What cancer taught Kaitlin Reagan about forgiveness

Summary

Episode Summary: “Brutally Anna” – “What Cancer Taught Caitlin Reagan about Forgiveness”

In this emotionally charged episode of Brutally Anna, host Anna Kai engages in a deep and heartfelt conversation with Caitlin Reagan, a beloved content creator known for her uplifting presence and authentic storytelling. The episode delves into Caitlin's personal journey through love, loss, and healing, highlighting the profound lessons she learned from her relationship with Francesco and his battle with cancer.

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1. Introduction

Anna Kai introduces Caitlin Reagan as a resilient and inspiring figure with nearly 4 million followers across TikTok, Instagram, and YouTube. Caitlin's positivity is rooted in overcoming significant struggles and losses, embodying the mantra: “We are not what happens to us. We are what we decide to do next.” (01:28)

Caitlin Reagan [01:28]:
"We are not what happens to us. We are what we decide to do next."

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2. Early Life and Upbringing

Caitlin shares her upbringing, raised by her mother and grandmother after her parents' divorce when she was less than a year old. Her father’s absence was marked by neglect and addiction, deeply impacting her sense of security and self-worth.

• Parental Figures:
  Raised primarily by her mother and grandmother, Caitlin had limited contact with her father, who remained in Pennsylvania post-divorce.

  Caitlin Reagan [03:05]:
  "My mom told him he was not coming home and she would leave if he didn’t fulfill his roles as a father and husband."

• Impact of Addiction:
  Caitlin recounts how her father’s drug addiction led to periods where her basic needs were unmet, fostering feelings of confusion and inadequacy.

  Caitlin Reagan [04:26]:
  "I was just confused because I was scared to say, like, hi, I’m hungry. Can somebody feed me?"

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3. Relationship with Her Father

Caitlin elaborates on the complexity of her relationship with her father, who struggled with addiction and depression. Despite his denial of drug use, Caitlin sought acknowledgment and understanding, striving to mend their strained relationship.

• Seeking Closure:
  After her brother's passing, Caitlin received a rare text from her father expressing pride and offering to reconnect, marking a turning point in their relationship.

  Caitlin Reagan [10:22]:
  "He texted me, and he was like, I heard about Francesco... I'm really proud of you."

• Efforts to Reconnect:
  Caitlin attempted to foster a closer bond through regular check-ins and creating a safe space for open communication, though full reconciliation remained elusive.

  Caitlin Reagan [12:02]:
  "I get sporadic texts like, 'How is everything?' and he's trying."

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4. Dance and Self-Identity

Caitlin discusses her 16-year journey in dance, describing it as both formative and challenging. Despite her dedication, she faced bullying and comparison to a more talented friend, leading to self-doubt and diminished passion for dancing.

• Bullying and Comparison:
  A particularly competitive environment left Caitlin feeling inadequate, which later influenced her pursuit of validation through social media.

  Caitlin Reagan [16:37]:
  "I spent all my life dancing in the shadows."

• Shift to Social Media:
  These early experiences propelled Caitlin into the world of social media, where she found a platform to express herself authentically and connect with a broader audience.

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5. The Relationship with Francesco

The heart of the episode revolves around Caitlin’s relationship with Francesco, her high school sweetheart. Their journey from innocent teenage romance to profound partnership underscores themes of trust, betrayal, and eventual healing.

• Early Relationship:
  Caitlin and Francesco met in high school, formed a strong bond, and moved into a long-distance relationship when Caitlin attended college in Florida.

  Caitlin Reagan [42:26]:
  "We got into a relationship at 15 and we were high school sweethearts."

• Breakup and Betrayal:
  The relationship deteriorated due to trust issues, leading to a painful breakup where Francesco accused Caitlin of cheating—a false allegation that left her devastated.

  Caitlin Reagan [45:30]:
  "He thought I was cheating because I wasn't."

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6. Francesco’s Battle with Cancer

Years after their breakup, Francesco reappears in Caitlin’s life, revealing his struggle with cancer. This revelation brings emotional closure and transforms their relationship, highlighting themes of forgiveness and unconditional love.

• Initial Diagnosis and Reconnection:
  Francesco confesses his illness to Caitlin shortly before passing, seeking forgiveness and closure for past mistakes.

  Caitlin Reagan [51:18]:
  "He texted me... I got true acknowledgment from him."

• Rekindled Relationship:
  Despite his diagnosis, Caitlin and Francesco reconnect, support each other through his illness, and use social media to share their journey, providing mutual support and inspiration to their followers.

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7. Lessons on Forgiveness and Healing

Caitlin emphasizes the importance of using personal hardships as catalysts for growth rather than sources of lingering bitterness. Her approach to forgiveness—both towards Francesco and herself—illustrates a path toward inner peace and resilience.

• Transforming Pain into Purpose:
  Rather than succumbing to anger, Caitlin channels her experiences into empowering herself and helping others, finding purpose in shared vulnerabilities.

  Caitlin Reagan [19:31]:
  "What good can come from this?"

• Embracing Faith:
  After Francesco’s passing, Caitlin reconnects with her faith, attending church and finding solace in spirituality as part of her healing process.

  Caitlin Reagan [60:41]:
  "I am on a journey of finding God again. I go to church every Sunday."

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8. Moving Forward and Dating After Loss

Caitlin navigates the complexities of dating after her profound loss, stressing the importance of self-discovery and authentic connections without rushing into relationships for validation.

• Self-Discovery:
  Taking time to understand herself and her needs allows Caitlin to approach dating with clarity and openness rather than seeking to replace Francesco.

  Caitlin Reagan [62:03]:
  "Learning about myself was crucial."

• Healthy Boundaries:
  Caitlin acknowledges the significance of setting boundaries and being honest with new partners about her readiness to date, ensuring that relationships are built on mutual respect and understanding.

  Anna Kai [70:18]:
  "You’re not wasting his time because you don’t know."

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9. Notable Quotes

• Caitlin on Resilience:

  “We are not what happens to us. We are what we decide to do next.” (01:28)

• Caitlin on Surviving Pain:

  “When you do good for yourself and put all that energy towards becoming something greater than you, you can't hate the world.” (19:31)

• Caitlin on Forgiveness:

  “I want to tell you I love you, you know?” (55:57)

• Caitlin on Finding Peace:

  “Now I'm on a journey of finding God again. I go to church every Sunday.” (60:41)

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10. Conclusion

In this episode of Brutally Anna, Caitlin Reagan offers a raw and honest exploration of her life's challenges and triumphs. Through her story, listeners gain insight into the power of forgiveness, the importance of self-love, and the resilience required to overcome profound personal loss. Caitlin’s journey underscores the message that even in the face of life's most brutal moments, there is potential for beauty, growth, and meaningful connections.

Key Takeaways:

• Forgiveness as Healing: Letting go of past hurts is essential for personal growth and peace.
• Authentic Relationships: Building relationships based on mutual respect and understanding fosters lasting bonds.
• Self-Discovery: Taking time to understand oneself lays the foundation for healthier future relationships.
• Resilience and Purpose: Using personal struggles to empower oneself and help others creates a purposeful life.

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Where to Find Caitlin Reagan:

• YouTube: CaitlinReaganTKAI
• Instagram: @caitlinreagan
• TikTok: @caitlinreagan

Follow Caitlin for more inspirational content and updates on her journey toward healing and empowerment.

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Join the Conversation:

Stay tuned to Brutally Anna for more episodes featuring inspiring guests who share their truths and help others navigate the complexities of love, loss, and personal growth. Follow Anna Kai on @maybeboth across social media and subscribe to Brutally Anna on your favorite podcast platform.

Transcript

[Caitlin Reagan]

Streaming December 12th on Peacock. Paris Hilton and Nicole Richie are back. That's hot. Loves it. For a show stopping reunion that will prove putting on an opera is anything but simple.

[Anna Kai]

We're really good at this.

[Caitlin Reagan]

One thing's for sure, they won't be upstaged. Good to have you back.

[Anna Kai]

Come on, we've got a show to do.

[Caitlin Reagan]

Paris and The Encore, a three part reunion special. Streaming December 12th only on Peacock.

[Anna Kai]

Being a marketer is no sweat. You just have to manage dozens of.

[Francesco]

Channels, launch hundreds of campaigns, score thousands of leads and.

[Anna Kai]

Okay, fine, it's a lot of sweat. Unless you have HubSpot's AI powered marketing.

[Francesco]

Tools to help you do all that and more.

[Anna Kai]

Get [e-mail] marketers. Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about but don't talk about enough. I'm your host, Anna Kai, AKA maybe both across social media. Here to remind you that life can be beautiful even when it's freaking brutal. So we were first introduced to Caitlin Reagan on YouTube over six years ago, and now she's amassed a following of almost 4 million followers across TikTok, Instagram and YouTube. And while she's mostly known for her uppy personality and Brooklyn twang, Caitlyn's positivity stems from a lifetime of struggle and loss. Here to remind us all that we are not what happens to us. We are what we decide to do next is Caitlin. Thank you so much for being here.

[Caitlin Reagan]

Oh, what an intro. Thank you for having me. Can I bring you everywhere with me?

[Anna Kai]

Dude, you are such an inspiration to me. We were just talking about this before we started rolling. We don't do small talk.

[Caitlin Reagan]

No.

[Anna Kai]

So I'm just gonna get right into it. All right. I went back, I stalked you hardcore. I went back to your first YouTube video you ever posted. It was like 31 fun facts about me, and some were very much not fun. You said you don't have a great relationship with your father, or at least you didn't six years ago. What was your upbringing like? I assume your parents were divorced, given how you've talked. You didn't have a great father figure in your life. So who was the parental figure? Was it your mom? Was it somebody else?

[Caitlin Reagan]

So I was raised with my mom and grandma.

[Anna Kai]

Okay.

[Caitlin Reagan]

My mom met my dad.

[Anna Kai]

That's why you're a girls girl.

[Caitlin Reagan]

I am such a girls girl. Literally, my mom and my dad, they did long distance at like a summer camp. And she always tells me to this day, never do long Distance. Because it's really hard to like, grasp who somebody is. She rushed into this marriage and she got married, moved to Pennsylvania because that's where he was from. And before I was even one years old, they got divorced. He just was not ready to be married or a parent even to this day when I ask him, I'm like, why? He's like, I just wasn't ready. And I'm like, that sucks because you made the decision. You know, like, it sucks, but at least you acknowledge that you weren't ready. Like, that's nice to know.

[Anna Kai]

Were they really young? You said summer camp.

[Caitlin Reagan]

Yeah, I know, I know. Weird, but 25, 20.

[Anna Kai]

Oh, so they were camp counselors.

[Caitlin Reagan]

I don't know what they were doing.

[Anna Kai]

Okay. I was like, were they at summer camp for 25 year olds? Yeah, I was like, were they like 12 when they were.

[Caitlin Reagan]

I know, Literally, it was weird.

[Anna Kai]

Okay.

[Caitlin Reagan]

Some sort of like summer. I don't know if it's like a.

[Anna Kai]

Camp or like a program or program.

[Caitlin Reagan]

Where all the, like, people her age would go. It was like something fun upstate. She just kept telling him after they got married and they had me, hey, like, you're not coming home and you're not doing what you're supposed as a father or as a husband, I'm gonna pick up and leave, you know? And she did. Cause he just wouldn't listen. And for majority of my life, from age 1 to about 12, I really didn't see him much because.

[Anna Kai]

Did he stay in Pennsylvania?

[Caitlin Reagan]

Yeah.

[Anna Kai]

And she moved you to Brooklyn. Is she from Brooklyn? Okay. So she was like, I'm gonna be close to family.

[Caitlin Reagan]

Yeah, she was.

[Anna Kai]

If I'm gonna do this alone, I gotta be near my mom.

[Caitlin Reagan]

Literally. She would try and have him see me as per. Like a divorce. And I think that's how it goes. Like, you have to share custody, literally. So I would go there to my dad and I would come back and I was so dirty. Like, my fingernails were black. Like, I just was hungry, you know, I would come back and tell her these stories and she was like, okay, we're going back to court and we're gonna discuss that. Like, this might not be like, safe.

[Anna Kai]

Wait, that's horrifying. You were hungry and dirty. That's your basic needs were not being met with. Do you remember that as a kid or do you only remember that because she tells you these stories now? Like, do you actually physically remember, like, being with your dad and I don't have anything to eat?

[Caitlin Reagan]

Yeah, I do remember. And I never really understood why? It's not like he was eating or my stepmom was eating, and I just wasn't like, nobody was eating. And I'm like, why is nobody hungry? You know, Like, I was just confused because I was scared to say, like, hi, I'm hungry. Can somebody feed me? I was just hoping, like, as humans, like, at some point food would be offered, and I was so confused. But as I grew older, I realized that drugs was a big problem.

[Anna Kai]

And this is where I was like, that's why nobody's hungry. So your father was addicted?

[Caitlin Reagan]

Yeah.

[Anna Kai]

Can you talk a little bit about.

[Caitlin Reagan]

Yeah, I actually, like, briefly just spoke about it online recently, but I never really talked too much about it, but. So I'll never really truly understand what drugs, you know, and how often. But my dad and my stepmom and a lot of my dad's side of the family, his sisters are still, to this day addicted to drugs. They're very, like, functionable drug addicts. Like, I feel like if you were to meet them, like, you'd be like, I'm torn if they're on drugs. Right.

[Anna Kai]

It's not, like, blatantly obvious.

[Caitlin Reagan]

It's not blatantly obvious. I wish that, because I've asked him a couple times, like, hey, will this ever get better? Will you ever fix this, like, recently, too? And he always just says that he's not on drugs. So I can't get, like, the proper truth. And I think that's hard because, like, you get to an age where you're like, this is so the truth. And, like, you keep.

[Anna Kai]

You know better now.

[Caitlin Reagan]

I know better now.

[Anna Kai]

Yeah.

[Caitlin Reagan]

I would love if you at the very least acknowledge it to me. So maybe I can help. Like, is there something that I could do to make this better for you? Because he's also, like, somebody that is depressed. So I always tell him, like, where is this coming from? And he's just. He can't understand himself because he's never sitting with his own thoughts because he's constantly being, you know, taking something to, I guess forget everything that's going on. I don't really understand the full extent, but what I do know is that I have a brother. He is my half brother. And that is why I even have a relationship with my dad at this point, because I love my half brother. We have the same dad, different moms.

[Anna Kai]

And he's younger or older.

[Caitlin Reagan]

He's 21.

[Anna Kai]

He's 21. Okay, so you're similar in age five years.

[Caitlin Reagan]

And I just remember at around, like, 12, 13, like, kind of like being like that mom figure. So when I got older and I was allowed to go back. Cause I would go see my dad's mom. So my grandma. Okay, I would be like, let me cook for him. Cause I knew he was hungry as well. So, you know.

[Anna Kai]

So you started becoming the parent.

[Caitlin Reagan]

Right. So to this point, when we got older and we had phones, my brother would call me. And we got so close. And when he got his license, he would drive to come down to New York and see me. And I remember one day we were sitting down, and he's like, you know, the drive isn't that bad. Like, I used to ask dad all the time, like, why don't we ever see Caitlin? I wanna see my sister. And he would say, it's so far. But it's not. No, it's really not. And he's like, you know, all along I thought that it was because of justified reasons. But, like, this is kind of messed up because it wasn't justified. Like, you just didn't want to go.

[Anna Kai]

Right? Exactly. Wait, did he grow up in the house with your dad? So your dad was his primary caretaker, whereas your mom was yours?

[Caitlin Reagan]

Well, so we have different moms. So he's my mom.

[Anna Kai]

Right, Right. No, exactly. But his mom didn't take custody of him.

[Caitlin Reagan]

Well, she lived in the house. It was them three. But she was also doing drugs as well.

[Anna Kai]

Okay, so your mom really was separate from that. Do you ever worry? Because I know a lot of children who have addiction in the family worry about it for themselves. Like, do you ever worry about, like, you drink casually? I mean, I've been. You know, that's how we met. We met at events, and you seem to handle yourself fine. Is that something you struggle with or worry about? Or is. Did you just not get that gene? It is genetic, I think.

[Caitlin Reagan]

Yeah, you're right. I think for me, I definitely learned as I got older, because we're constantly learning about ourselves, that I do have an addictive personality. So in an ideal world, if I lost control, I could get addicted to anything that I take. Like alcohol or maybe smoking a vape.

[Anna Kai]

Yeah.

[Caitlin Reagan]

But acknowledging the person that I am, I can take control of my life and say, okay, like, I know this could happen, so let me be on top of it. I think that when my brother, being a little bit younger, 21, he's like, having his party phase. The girls I get worried for for him.

[Anna Kai]

Right.

[Caitlin Reagan]

Because again, like, my mom took me away. So it was a little bit of a different situation. But for him, this is Kind of the norm, and I worry for that.

[Anna Kai]

Your mom never struggled with any of that?

[Caitlin Reagan]

No, thankfully. And I think that's why she, like, was like, holy shit. Like, the long distance, because she had no, like I said, functionable drug addicts. Like, I was even, like, how would you not like. I feel like I'm so good at character. How did you not speak up on what the hell happened? I'm so disappointed. Horrible judgment. Horrible Allison. But she was like, I. I swear I wasn't there for it. I'll give her the benefit of the doubt.

[Anna Kai]

But wait. You grew up very, very quickly, whereas I think the average. You know, I know when I was 24, 25, if you feel a sense of security and the age at which your brother is at right now, you feel invincible. You're like, nothing can touch me. I can do whatever. You know, that's why people experiment so much in their 20s, and you saw what can happen when shit goes awry. And so you have a very mature presence. Life just handed a lot of stuff to you that I think you were probably, I think, too young to have to handle.

[Caitlin Reagan]

Yeah.

[Anna Kai]

Has your relationship with your dad changed now that you're an adult? And, you know, obviously, I'm sure he knows.

[Caitlin Reagan]

Yeah.

[Anna Kai]

How successful you are now. What is your relationship with him like now? Do you drive to Pennsylvania?

[Caitlin Reagan]

So when Francesco passed away, and I know we're going to get into the whole. Oh, we'll get into Francesco.

[Anna Kai]

Yeah.

[Caitlin Reagan]

He texted me, and he was like, I heard about Francesco because he met him. I would bring Francesco there a couple times. See my brother, my grandma, my cousins, he said, I heard he passed away, and I don't know much about you, but, you know, based off the fact that you were there till the very end, I'm really proud of you. And I read that text, and I think for the first time, I got true acknowledgement from him, and it was really nice.

[Anna Kai]

Yeah.

[Caitlin Reagan]

So I texted him back, because when you're at rock bottom, like, you're looking, you don't have any more hate to give. You're just done. You're tapped. So I wrote back, and I said, hey, listen, I really appreciate this text, and if you ever want to sit down and get some dinner and get some lunch, just want to let you know it's not too late. I love that because I think he was scared. And to this day, he's very, like, a little bit on eggshells because I think he's very scared of, like, rejection, which is really interesting. So I always try to Go into having conversation with him, like, making him feel very safe, like, I'm not gonna run. I know you know that you messed up, but it's okay. Like, let's try. After that, he didn't necessarily take me up on a dinner opportunity, but I would go down during the summer to see everybody, and he would come up to me and have a little conversation like, hey, how's everything going? And I saw that, like, I would sit down and like, pick his brain, he'd pick mine. And we were naturally, like, kind of falling into line. And recently one day I said, hey, like, I'm gonna leave Pennsylvania, but when I get back to New York, you think I could get a text, how you doing? Maybe like once a week, little check in. Like, that's how I like, kind of like, play when I'm like a joke. I like, try to, like, loosen up and make him feel loosened up. And he's like, okay. So ever since then, I get like, my sporadic tags like, how is everything? I heard. I just went on a talk show recently. How is the talk show? I got to watch it. You know, he's trying. That's gonna ask at this point.

[Anna Kai]

But you know what? It's also great because I think it's almost nice that he has humility about where he came from, because it shows that he's not like a sociopath. And he's like, oh, you know, I deserve to be in your life. Cause there are parents like that who totally drop off the face of the earth and they come back and they expect, like, they should have a relationship, like they're entitled to a relations. And I think what's nice about your dad is that he knows. He fully is aware. And I think that's why it's so nice that you are giving him permission to be in your life, because the ball really is in your court. You know, I think humor unites us all. So it's great that, like, you're using humor as a vessel to connect with him. But I think by doing that, you've given him the opportunity to be like, you know what? She does want me in her life. I'm not intruding because at this stage, I'm not entitled to be in her life. I didn't raise her. So I think it's a good thing in a way, if we want to reframe it like that. He fucked up when he was younger. All do. Some of us less than others. In that video of yours, you were talking about how one of the most traumatizing moments for you as a kid was he was supposed to come spend the day with you? I think it was a Christmas.

[Caitlin Reagan]

Was it?

[Anna Kai]

And you waited all day for him and he never came?

[Caitlin Reagan]

Yeah. Like, yeah, that happened a lot. He was.

[Anna Kai]

Yeah, that was just the one time.

[Caitlin Reagan]

It was a lot. And I. It's interesting because till this day, I struggle with not feeling, like enough. I don't know, in my everyday life. And I always, like, what is going on? Because, like, I've proven to myself, like, I do such great things. Where is this coming from? And I. My therapist, like, helped me kind of realize, like, well, when you're waiting by a window for somebody and your people, like, you're two people that put you on this earth, you're not. They're not showing up for you.

[Anna Kai]

Right.

[Caitlin Reagan]

You don't. You naturally, as a kid, like, well, then I guess I wasn't enough for him to come. Right. And so this is still something to this day that, like, I'm battling, like, learning, you know, how to, like, heal from that.

[Anna Kai]

I mean, aren't we all? It's like, I was lucky enough to have great parents growing up, and they were married, and we didn't have a lot, but they raised me in a loving household. I actually grew up in Pennsylvania. Where in Pennsylvania?

[Caitlin Reagan]

Westchester.

[Anna Kai]

Stop.

[Caitlin Reagan]

Is that where you're from?

[Anna Kai]

I'm from Malvern.

[Caitlin Reagan]

Is that close? Like, King of Brexit?

[Anna Kai]

Yes, it's next door to Westchester.

[Caitlin Reagan]

Wow.

[Anna Kai]

I grew up never really feeling like I belonged because now I think there's a lot more diversity in that area. But growing up, this is the 90s, and I never felt like I belonged because it's also a fairly affluent area, and I grew up with immigrant parents. So it's, like, interesting growing up in a very, like, wealthy area, but being the poorest kid there and not being able to keep up, I think that affected me so much. And, like, you know, I think kids can be so mean. I couldn't afford all the nice clothes and, like, this stuff that other people did and something as basic as, you know, my mom's Chinese. Chinese people don't bake. They cook. You know, they saute. But there's no culture of, like, baking as much for your birthday when you're 10, your mom bakes cupcakes for the class. Like, my mom never did that.

[Caitlin Reagan]

Gotcha.

[Anna Kai]

Not because she didn't want to or whatever, but, like, she would do other things that, like. And she's showed me love in so many different ways. But when you're 10, you don't realize that, like, you have other things and you have love in other ways. I just felt like I didn't belong. And so I think it's a similar thing to you where it's like, for me, it wasn't coming from my parents, but it was coming from school. And so this leads me into. My next question is like, I feel like such a huge part of the reason I, from a very young age, wanted to perform, I wanted to be on camera, I wanted to be in media and entertainment, was because I felt so unseen that my need to be seen, it was, like, overcompensating. I was like, I need to be so special and so glittery that, like, nobody can ever ignore me again. Yeah, everybody, I think, who decides to put themselves out there in this way is a little crazy. And I say that in a loving way. I'm like, what we do is kind of nuts, right?

[Caitlin Reagan]

Yeah.

[Anna Kai]

And everybody has a point at which they're like, I'm going to risk a lot to try and do this. Like, what was that for you? Do you think it comes from the fact that you felt like you weren't seen as a kid?

[Caitlin Reagan]

I'm going to be honest, that was a great question because you have my brain going right now. I have never thought about it in that way, but I would say absolutely. I remember before social media was even a thing, like, in elementary school, there was a thing called, like, Project Arts. And I just. I always wanted to be a part of, like, being on stage and dancing and singing. And I was very. Not only, like, adamant about it, but, like, pushing for it. Like, I was, like, going up to my teachers and say, like, hey, like, I want to do this and I want to do that. And they're like, this kid, really, like, someone give her a role. Like, this is interesting, you know, so.

[Anna Kai]

Yeah, because you were a dancer for 16 years, right?

[Caitlin Reagan]

Yeah, yeah. My dancing. My dancing life, I would say, was not something that I loved. Wasn't really, like, the best experience for me, but definitely built me into who I am today.

[Anna Kai]

Why was it not the best experience? Experience?

[Caitlin Reagan]

I had a best friend from my elementary school who I. I started off at this dance studio, and I don't know what happened, but I guess, like, my parents told her parents, like, she should come dance at the studio. She came to this dance studio and they loved her so much. She was so good at dancing, and she just was better than me, and that's okay. But nobody held space that, like, that was hurtful like, that I wanted to be as good and Instead of using that as motivation, I fell victim and said, like, I'm not a good dancer and like, I'm gonna own that, so I wouldn't really practice. And like, I spent all my life, like dancing, like in the shadows entirely, you know, I was also kind of bullied in the dance studio. There was times where better dancers would all sit at a table and I wasn't necessarily welcome there. It was a little bit. It wasn't. It was okay.

[Anna Kai]

I think that's really tough too. Especially in, like, performing arts. Some people are just like, naturally better. Singers, dancers, actors, whatever. And like, it's tough because I think human nature is to compare yourself. I think when you're that young, you don't have the skills to process. Like, hey, you know what? Even though she may be a more naturally gifted dancer than I am, I am probably more naturally gifted than her in something else and I should go do that thing. Instead of trying to be as good of a dancer as her. Like, maybe you're a better. You know, you're an amazing storyteller. Obviously, now this is your career. Like, that's your strength. But what is the quote? I'm probably going to butcher it. It's like, you know, if you're a fish and you spend your life trying to be a bird, you're going to think you're a failure. I'm fucking that up. But it's basically like, if you spend your life believing that you should be something that you're not, you're never going to actually get good at what you're supposed to be getting good at, you know? And obviously now you're here and like, you know, you are the after. But I think at the time, it's like, if you had been taught, like, you should just try and be a dancer, you'd fail because it's not what you were meant to do, right?

[Caitlin Reagan]

Absolutely. My mom used to always say too. I'd come home and cry and she'd be like, it's always the guys in the back corner that one day. And now my dance studio would be like, hey, you want to come do an event here? And I'm like, you guys forgot about me my whole life. But maybe just cause I don't hold hate in my heart.

[Anna Kai]

But that's the thing. You are so not bitter. Which is something I struggle with because I like to say, I mean, I've kind of owned it too. Like, I feel like part of my charm, if we can call it that, is like, I'm angry. I like, I've owned my anger. I'm angry at, like, the shit that's happened to me. I'm angry at the stuff that, like, you know, from 25 years ago that I probably shouldn't be angry about and comes up in therapy. How do you manage to grow up the way you did? And on top of that, you lost your. The love of your Life at, like, 24, 25. How do you go through that and not just be angry?

[Caitlin Reagan]

I think when everything happens, I, like, take the situation. I'm like, what good can come from this? Even though that sounds so weird, like, what am I supposed to learn here? And what can I become from this? And instead of spending so much time falling victim of a situation, I would use it to make myself better. And I think that the biggest revenge because, like, sometimes, like, you hate the universe and you're. You could be just mad at not no one specific, just life. I. I feel like when you do good for yourself and you put all that energy towards becoming something greater than you, you don't. You can't hate the world almost, you know, like, you're like, I. I'm so proud. All I can focus on is, like, what I can control, which is, like, me. So I think that's kind of like where I am. Like, I. I think if I let everything happen to me and then just like, completely lost control, never went to the gym again, looked in the mirror, was so disappointed with how I looked or just completely spiraled, then I would hold that hate, you know? So I think using it to become more than. And acknowledging that, like, it doesn't end here, like, really helped me to just be at peace.

[Anna Kai]

It reminds me of something you said in one of your videos, that I always wonder what it would have been like growing up if I had somebody that pushed me, that would have told me I could do it. Because you didn't have a ton of people in your life that were like, hey, you can be a star one day, right? And I think what's so awesome is that you didn't have that. You didn't have the stage mom, and you didn't even really have much of a dad, and you did it anyways. And I think so often we become what we need. Your mom, was she supportive of your dreams? Obviously, she raised you as a single mother. So do you think a lot of your grit comes from her? And what did she do to support you guys growing up?

[Caitlin Reagan]

I was just going to say I think that my mom did a good job at making me feel like I could be A potential star. The thing that, like, I wish that my mom did better was that when I would finally accomplish one specific thing, instead of, like, helping me celebrate that win, she'd be like, but what about this?

[Anna Kai]

The next thing. Right, the next thing. And by the way, so Asian. She's not Asian, obviously. That's like, Asian mom or Asian parents are just like, oh, you got an A. It's a stereotype. It's like, you got an A minus. Why didn't you get an A plus?

[Caitlin Reagan]

Literally. Okay, well, glad to know it's not just me. So what ended up happening was that I spent majority of my life, even though I don't think she meant to, feeling not again, not enough. Like, not like I'm never accomplishing anything. Cause I wasn't taught to necessarily celebrate wins. I was taught to just, okay, you did this. That doesn't matter. There's a million other things on the list, you know, And I think that's where she could have done a little bit better.

[Anna Kai]

Do you talk to her about that?

[Caitlin Reagan]

Yes, but we.

[Anna Kai]

It's so tough talking to our parents.

[Caitlin Reagan]

About what they could have done better.

[Anna Kai]

What they could have done better. I don't.

[Caitlin Reagan]

You don't like that. I know.

[Anna Kai]

I just, like, you know, I don't.

[Caitlin Reagan]

Like it either, but.

[Anna Kai]

And I think there's a part of me that it's like, you did such a good job that, like, I don't know if I could have done better given the circumstances. Like, you think about you as her. It's like, would we have done much better? I mean, we're all just making it up as we go. Right? So you have talked to her about it, and what has she said?

[Caitlin Reagan]

She says, oh, but you knew what I meant. No, I didn't. That's why I'm here right now to have this conversation. Oh, but I. You know, it's always like, but this is what I did do. But I'm not talking about what you did because I've already acknowledged that in another breath. Let's talk about what you didn't. That's okay to hold space for that, but there's such a defense mode. It's very hard to properly sit down and really be heard sometimes.

[Anna Kai]

Do you wanna be a mom? Do you want a family in the future?

[Caitlin Reagan]

I do.

[Anna Kai]

Okay, so you know what you're not gonna do going forward? You have so much life experience behind you these days that you're not gonna repeat the same mistakes that your parents made at all.

[Caitlin Reagan]

No, you stop the cycle here.

[Anna Kai]

Yes, exactly. Generational trauma does not have to continue on. So it's interesting that you said that, like, your mom always wanted you to go after the next thing. And I think that's a common thing in our industry specifically, is because we do such a public thing that everybody's always comparing to the next big thing. It's like, okay, you got a win, but somebody else got a bigger win. And you had said in your video that you care way too much about what other people think of you. I love that you admit that, because I feel like that too. Do you still feel like that, though? It's been six years since you made that video? I know how I feel about the way other people perceive me and how that's shifted as I've grown up. But I'm curious to know.

[Caitlin Reagan]

I've come such a long way. I think that at this point, what makes it different is that even though I may care to a certain degree, it won't stop me now. I'll still do what it is knowing that this is gonna cause some. Some noise and be okay with the noise. Even though when I get the noise, I'm still gonna sit with it and have to deal with it.

[Anna Kai]

It still stings.

[Caitlin Reagan]

It still stings. I think that when you lose everything and, like, you really do inner work, you get a good, better grasp of who you are. And when you, like, look in the mirror and you're like, oh, this is who I am. But why is everyone else saying this? Then I'm like, oh, my God, they just don't know me. How can anybody from a screen know me the way I know me? And I'm like, wait a minute. I'm letting people that proof that this is a fact don't know me. What am I doing here? I have to, like, walk in integrity and my dignity, because that's the only way. Like. Cause you lose sight of that. Cause you're like, sometimes I feel like when you're weak. And that's why it's so important to really do inner work and heal and be proud of who you are and confidence. If you don't know who you are, like, you're gonna think other people know better.

[Anna Kai]

If you don't know who you are, you're gonna become everybody else. Everybody else I will never stop caring about. I mean, I applaud the people who say, like, I genuinely don't care about what other people think about me. I'm like, that is so freeing. I was like, I do. I will always care, but I will never let it stop me. It's really hard because you realize, like, other people probably think you're crazy. And I had some people say some things to me. It's like, you know, this is a hobby, like, do you really want to be doing this? And so did you have any naysayers? And maybe they weren't like, hey, you're crazy, but you could just tell. Maybe they were not as supportive or thought you were crazy.

[Caitlin Reagan]

I would say that it wasn't necessarily where people thought I was crazy of what I was doing. It was how vulnerable I was online. Like, don't put your dirty laundry out there. Like, what are you doing? Like that part of it, like how vulnerable and how honest I am with everything that I've been through is what people say is like almost psychotic. So I'm like, am I insane or do I just have a passion?

[Anna Kai]

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[Caitlin Reagan]

The world and really have these serious conversations and be okay with it and as long as it's helping somebody. With everything that I've been through, through it all, what has made it just a little bit more worth it was the fact that there were so many people getting, like, gaining some sort of something from what was going on that, you know, even for Francesco, he was like, I'm so happy. At least that number one for me, I know I'm not alone. And number two, like, they don't feel alone. So, like, everything that we did, like, this whole social media thing and, like, being so vulnerable just really gave us purpose.

[Anna Kai]

Right? You're not just famous for no reason. You are actually helping people.

[Caitlin Reagan]

Yeah.

[Anna Kai]

I feel like my audience helps me and I help them. It's a very symbiotic relationship. You sharing your whole life is so interesting because it's like, I wonder if it's like you could never share as much as you wanted with the people that you were supposed to be able to share everything with growing up. So you're like, I'm just going to lay it out there.

[Caitlin Reagan]

You are just blowing my mind today.

[Anna Kai]

You were searching for a connection with your father. And, like, you know, in a way, I think you obviously are very close with your mom, but it's like you couldn't talk to them the way that you needed. And like, I wonder if so much of your desire right now to share is because you didn't have an outlet. I'm not. I don't know. This is just like a hypothesis.

[Caitlin Reagan]

That's it. Yeah, that is it. I mean, wow. I even, like, I. When I was younger, not so much anymore. Like, in my early 20s, like, anywhere from like 19 to, like, 22. I had, like, friends in every angle, people coming in and out of my house. My mom was like, what is this, a frat house? Like, so many friends. And she's like, what are you doing with all these people? And I just had, like, this passion to just Gather as many people and be around as many people as I can. And my mom's like, do you ever want to be, like, alone or, like, maybe one or two people? And I just needed all these people. And then when I got older and started to, like, understand, like, okay, like, there's. There's some problems here with some of the people around me. This doesn't make sense. And I kind of got myself back to center and I lost all those people around me. And I. I kind of found it from the outside world with social media. So I'm still living out, like, that desire.

[Anna Kai]

Yeah. You have everybody in your phone now when your mom's asking you, do you ever just want to be alone? It's like, mom, I grew up alone in my head, wanting to find connection, and that's why I'm here. You're the daughter of a single mom. I can't imagine things from a financial perspective were that easy for you guys growing up. Am I correct there to assume that?

[Caitlin Reagan]

Yeah. Okay. So we grew up and we lived. It's so funny that you asked me that. And I think the reason why I was never really, like, so vocal about it is because everybody in my family is very like, like the mob. Like, oh, we don't talk money. I'm like, why not? How much money you got?

[Anna Kai]

A generational thing, too. I think that's generational.

[Caitlin Reagan]

I'm like, I'm your kid. Why do I not know how much you got?

[Anna Kai]

Right?

[Caitlin Reagan]

But I just knew that to be a competitive dancer was like X amount a month. I was a middle class kid. We lived in, like a little apartment. I remember, like, my Christmas tree was a little tiny, and I used to go to other people's houses and, like, they have, like that beautiful big tree. So I knew that I wasn't racking, but I had what I needed. Where I never felt like I couldn't go on like a senior trip, for example. You know what I mean?

[Anna Kai]

Right.

[Caitlin Reagan]

So I would say I was very solidly middle class.

[Anna Kai]

But you knew you were like, I gotta make some money when I grow up if I want to live. I don't have, like a trust fund or.

[Caitlin Reagan]

Yeah. If my mom was very content having just the, I guess, like your average.

[Anna Kai]

Needs, her basic needs fulfilled. Yes.

[Caitlin Reagan]

I'm like, no, you're like, I like my Chanel, you know, like, because I went to college in Miami, like at Boca, which I was always in Miami, and I saw this lifestyle and I'm like, I don't need all this. This is a little Too, Too much.

[Anna Kai]

Miami is. Yeah.

[Caitlin Reagan]

I was like, everything.

[Anna Kai]

You literally thought.

[Caitlin Reagan]

And I was like, okay. But I acknowledge that there's more to what I knew.

[Anna Kai]

Right.

[Caitlin Reagan]

You know, and that if I didn't go way to college, I would have not known that.

[Anna Kai]

You go from kind of zero to everything in social media. Right. I think you're doing well now. How do you budget? How do you handle your finances? Because I grew up very middle class too. I remember like having to learn how to open a 401k on my own and nobody taught me about personal finance. I didn't realize, like, you can't apparently you're not supposed to let cash just sit in a bank account.

[Caitlin Reagan]

I just learned that too. Yeah.

[Anna Kai]

Somebody was like, oh my God, no, you gotta invest in them. Like, what do you mean? They're like, it depreciates every year. And it was like just this mind boggling thing to me because I was like, what do you mean? I can't just put it in a savings account that's bearing 1% interest a year. They're like, inflation's what, 5% a year? I don't know. It's something crazy. So how did you learn how to handle your money? Have you learned. Should we talk about this?

[Caitlin Reagan]

Yeah. No. So I, like you said, I never had anyone to explain it to me. And I met somebody recently who actually started off that he wanted to take me out on a date.

[Anna Kai]

Okay. But you're like, he's now my financial advisor.

[Caitlin Reagan]

He really is.

[Anna Kai]

You're like, didn't work out that way. But he handles my money, which is also scary.

[Caitlin Reagan]

I know.

[Anna Kai]

I'm joking. No, literally, I'll let you talk.

[Caitlin Reagan]

No, no, it's okay. So we went on his date and he like owns like a bunch of places and I was very. I wasn't into him romantically and I communicated this to him. But I did tell him that, like, I think that he'd be like a great friend and I really admire how much you've created for yourself. And he was really respectful of me not wanting a romantic relationship, although probably hoping that I would change my mind. But he is the one that has said, make your 401k and explain to me all the different ways to not have to pay so much out on taxes each year.

[Anna Kai]

You got a lot of business expenses.

[Caitlin Reagan]

Literally a lot of business expenses. For sure. You could pay out your personal account X amount a month and you don't have to pay taxes that. Your 401k every year put in X amount. You don't have to tax on that. So he's. I'm fairly new to really learning how to, like, be smarter with my money. But I've. Up until this point, I've lived at home. And I actually am moving to the city soon.

[Anna Kai]

That's so exciting.

[Caitlin Reagan]

I know. So this is gonna be like, finally. So I'm subleasing during the summer.

[Anna Kai]

Okay, great.

[Caitlin Reagan]

Just to see this air financial district.

[Anna Kai]

I have lived in so many apartments in Fidi. Okay. That is amazing. I love Fidi. I think it's like a hidden. Yes. Okay. I would love to move back there.

[Caitlin Reagan]

I just like the high buildings. I need some.

[Anna Kai]

I love new windows. You need the natural light for the videos. Oh, my God. Nothing beats the natural light from a high rise in this city. Nothing.

[Caitlin Reagan]

I'm a little bit weird. I always thought that I was good with change, but I don't. I don't really like it. And I know that's, like, normal, I think, just crazy.

[Anna Kai]

Because you've been through so much.

[Caitlin Reagan]

You would think I like it so.

[Anna Kai]

Much else that I'm like. It's way more traumatizing that than, like, just moving to a nice apartment.

[Caitlin Reagan]

You know what? I think because of all the trauma, I've kept a couple things that, like, make me feel comfortable.

[Anna Kai]

Yeah.

[Caitlin Reagan]

And like, my home and like, my surroundings. And like, being close to Francesco's family that's like, two blocks down has been like, help has helped for so long that, like, at this point. Cause I've healed so much. I'm like, I'm ready to now take this next step. So I think that's why I'm a little bit scared. Cause I'm like, I know what I'm doing here. Like, it's deeper than, like, taking that move.

[Anna Kai]

Yeah.

[Caitlin Reagan]

So.

[Anna Kai]

But you're excited too, right?

[Caitlin Reagan]

I am. And I love. The one thing I love about me is even though I'm scared of something, I'll still do it.

[Anna Kai]

Yeah.

[Caitlin Reagan]

And that's what's most important.

[Anna Kai]

And, you know, I think the best things in life come from when we're scared and excited at the same time. If you're just scared, it probably means you're about to do something really stupid, you know? But it's like, if it's a mixture of scared and excitement, it probably means something great is going to happen. There's actually a very small window in your life that you get to live alone. I only lived alone for three years, and then I met my husband, and then we moved in together. And so for you, you've Lived at home with your mom, and now you're moving out on your own. Who knows when you're going to meet the next person. So you're never going to go back in time and get this time back. So you should just really enjoy living alone while you can, because, trust me, I love my husband, but my God, the way he will load a dishwasher. I am just like, what? You know, nothing is ever. When you. Even when you find your person, you're like, the way you do shit around the house, I'm like, that's where you put that cup, the wine glasses, where the coffee mugs are. Like, why would you do that?

[Caitlin Reagan]

Right?

[Anna Kai]

So you get to have your space exactly as is. Which is.

[Caitlin Reagan]

Speaking of your husband, do you think that you ever find everything that you're looking for out of somebody? Like, is that a realistic expectation?

[Anna Kai]

It depends on what your list is. I never had a running list in my mind of like, these are my non negotiables. And I hate questions like that almost when people ask me, because it feels so limiting. I needed somebody who was financially stable. I agree, because I was not in the position you are now. When I was 26, I was making a decent living. I was a real estate agent in the city. I was a struggling actress and I did real estate because it afforded me the opportunity to audition because it's flexible. So I was doing fine. But I was like, I cannot support a family off of my income and I don't know what my life is going to look like. I was a creative, and so it was not so much about, I want a guy to take me on vacations. I was like, if I'm going to have a family, I cannot subject my future children to this instability that is my life. Like, my husband at least needs to be stable. And I will provide a lot of other things. Like, we have a fairly traditional relationship in the sense that obviously we both work now and we're both contributing financially, but I am still primarily the CEO of the house, like a lot of women are. So my thing was I need him to be financially stable. I need him to be very family oriented. And those were kind of like, I'm very, very close with my parents and I'm like the daughter of immigrants. So like I've said to my husband, I don't ever want to put my parents in a nursing home. So if it ever comes to the point that they can't live on their own one day, hopefully very far into the future, they're moving in, or we're building, you know, a guest house or. Or something. If we were lucky enough to have the means to do that, it's like they're not going. Cause that's not like our culture. And like, I see it as. They raised me when I was, like, incapacitated as an infant. If and when it comes time to do that, and it may never happen. I mean, my grandfather lived on his own until the last day.

[Caitlin Reagan]

Wow.

[Anna Kai]

He had help in the end, for sure. But he was 95, living in his own apartment. He was never in assisted living. I knew those were my two qualities. And beyond that, I was open. And I think on paper, you wouldn't understand why my husband and I mesh because we come from very different backgrounds, but, like, we have the same values, and those values are what's important. And so, you know, I would love to know what your core values are, because for me, I think the reason why we've worked so well, we're both weird in the same way. We are both very, very into our careers. So that's why. And we've waited to start a family because we're both not, like, it would be really problematic if I was really into my career and I wanted to wait to have a kid. And he was like, no, I want to be a dad today. So that's. I think more important is that you're both weird in the same way when you think about it, because you were in such a long term relationship, Francesca. Which we need to go back and we will dive into that. But what are your values and where do you see your life More so in 10 years? And how does a partner fit into that?

[Caitlin Reagan]

All right, so. And I think I'm exploring this as I go right now too, so I.

[Anna Kai]

Forget you're so much younger than me. I have space for me, which is amazing because you have such an old soul. But. Do I? You do.

[Caitlin Reagan]

Okay, Good to know, y'all.

[Anna Kai]

She's 26 and I am 33. And it's like, I remember being 26 and I did not have my shit together.

[Caitlin Reagan]

All right, I'm going to tell you what comes to mind. So I am a person that really values, like, my goals and my career and, like, what I do. And I think I would love a person that has that drive in themselves, whatever that is. And I think that I want the man. I want to be so important to him, but I also want himself to be, if not just as important, like neck and neck or a little bit less than. I just want him to, like, care deeply about himself. As well. And I don't know if that sounds weird.

[Anna Kai]

No, no, no. You want him to have his own thing?

[Caitlin Reagan]

Yes. Yeah, I want, like from Monday to Friday, while I'm going here, he's like, perfect. Cause I'll be here. And obviously, you know, when you think children, as I'm speaking right now, I'm like, ooh, like, how would this work? But I'm sure, I guess when we get there, things would change. But I guess, like, at the core, that's who they are. And like, we'll obviously make those adjustments as like, like we evolve. But I just. That's something very important. I also really family oriented as well. A true ride or die. Like, if I'm sick or if something, you know, you're there. Like, you know how many people said to me when Franchesca was sick, like, I. I honestly, like, at this age, like, I would have left, I just wouldn't have been able to do it like that. I, like, hold space that, like, you know, that some people just can't. But I was like, I.

[Anna Kai]

You couldn't imagine doing that, can you?

[Caitlin Reagan]

Like, I would hope somebody would be there for me, like, truly, like, ride or die, like, there till the end. Like, you love somebody so much that, like, just un. True love. I wonder if, like, in our generation, like, we're like, losing sight of, like, what that really means.

[Anna Kai]

I think a little bit, because I think we think of relationships so much as it's almost like a business transaction now, when you ask me, it's like, did you get everything you wanted? Or do you think it's possible to get everything you wanted? It's like, you know, you could drop the perfect man, but at the end of the day, the perfect person. It's a feeling. It's not so much a list. I think we are losing it a little. And I think maybe because we are spoiled for choice now, that's why. Because we have so many options, Right? Before, it used to be who's in your community? Who does your mom or your friend know? And then who can you meet at a bar on a Friday night? Now I could go meet a thousand guys with the swipe of an app. And that fucks with you.

[Caitlin Reagan]

It does. You know it does.

[Anna Kai]

So now I want to switch gears a little, and I want to talk about Francesco to people listening who are not aware of your story. Can you just take us back?

[Caitlin Reagan]

I got you. Okay, so there was this boy who was at my dance studio, and his name was Francesco. He was the breakdancer. So around the age of like 11 or 12 years old. He was like the popular guy of the studio. And like I said earlier, I was not, not one of the best dancers there. So I was a little bit intimidated, but I had a little crush on him. And I wasn't definitely not seen by him because he was with all the girls that danced better. He ended up leaving the dance studio because of grades in school and like, he wasn't able to balance both. And I was like, well, this sucks because, like, not only did I not get to like, properly like, introduce myself, but I probably won't ever see him again. So at a very young age I was like, oh. And years go by, four or five years, and my best friend is like, just starts high school. And she's like, there's this hot guy everybody's talking about. And she's like, his name's Francesco. And I'm thinking in my head, I'm like, that name sounds so funny.

[Anna Kai]

There's like not that many people named Francesco.

[Caitlin Reagan]

Wait a minute, like this is ringing a bell. What's the odds it could be him? So I tell her I'm gonna come pick her up from school just to go see him. And I run into him and he's like, I feel like I know you. I'm like, oh, no way.

[Anna Kai]

But like, I've known.

[Caitlin Reagan]

I know you, but you don't even know that. But we just. From that from there on. We got into a relationship at 15 and we were high school sweethearts. We had a beautiful relationship while we were in high school. He was like very popular. I was a little bit more. I didn't have time for like a social life. So it was like school dance, homework, bed, school dance. Like he was like, school chillin, cool guy, like hanging out after hours. So. So I was like, he was like my world. And I don't think I was necessarily his just because he had so much going on. But you know, he really valued me. Would come over and pick me up from dance all the time. But when I went to college, I went away to Florida. I asked him like, do you want to do long distance? And he was like, yeah, like, I don't want to lose this. So when I went away to college and now he didn't go to college, but he was working. What happened was, is no longer was I to girl with this tight schedule. I'm a girl, like one class a day. And like, life is different.

[Anna Kai]

College is easier than high school. I thought it was because high school is all about getting into college. And Then you get into college and you're like, I have nowhere to go after this, so it's fine.

[Caitlin Reagan]

It was crazy. I was like, holy shit. Like, I don't have to do a whole day of classes. Like, what? So we would just all meet up and go on boats. Like, this is Florida. And he was like, what is going on out there? And, like, slowly but surely it went from now. Instead of him being the popular guy after school, he was just working all day. And now I turned into the girl where, like, he wasn't. I was his whole world. And now he wasn't necessarily mine. And it kind of switched. And he wasn't used to that. We ended up breaking up because. Trust issues. And he just, like, sourced so much going on.

[Anna Kai]

That's young. That's. I mean, it's such a young age.

[Caitlin Reagan]

It was, you know, both kind of just on different paths at that time, and it just wasn't working. But he. We broke up, and because he cheated, he thought I was doing something wrong. And so he just.

[Anna Kai]

He cheated because he thought you were cheating?

[Caitlin Reagan]

Yep.

[Anna Kai]

Yes. That's a lot to unpack. But, yeah, that is. I know, because he was like, you know, it's like. It's almost sad because it's like he probably didn't want to cheat, but he thought you were cheating because you had all these options now.

[Caitlin Reagan]

He had this motto where it's like, you always cheat first before they do, so it doesn't hurt so bad.

[Anna Kai]

And it's like, it's a defense mechanism.

[Caitlin Reagan]

Defense. And I was so confused. If we really want to, like, I was going to just, like, brush through it, but I was very hurt because when, like, somebody's so convinced that you're doing something that you're really not, how do you change that?

[Anna Kai]

I know.

[Caitlin Reagan]

I literally was. I would sit there and beg him to believe me, but you just can't. You just like, this is your world.

[Anna Kai]

That's a hidden. That was a Francesco. Insecurity thing that he needed to figure out. And I think it's tough because he was Mr. Popular. He was. It's like, he didn't have to try growing up, and now all of a sudden, he has to try. And so, you know, maybe to somebody else, they would be like, yeah, this is just life. But to him, it's like, wait, I'm not used to this. So, you know, we do immature things when we're young. You guys were so young that. How did you find out that he cheated on you? Did he tell you or. Well, did he Let you find out, because that was probably the goal, to make you jealous a little bit.

[Caitlin Reagan]

That would have been nice. No, it was the complete opposite. I saw that he was struggling with the distance and I saw that he was struggling with how, like, she's doing all these cool things, like, how can she still love me the same like she does? That's why, like, I'm insecure. Maybe she's cheating. So I was like, you know what I'm gonna do? I'm gonna book a surprise flight home for Valentine's Day to surprise him, to show him that I've cared all along in it, you know?

[Anna Kai]

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[Francesco]

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[Caitlin Reagan]

So I get home and I show up to his door and he was so happy. A little bit off, but very happy. And he's like, I have this taekwondo. Cause that's what he did at the time. He's like, I have a show in Times Square tomorrow. Like, come. And I was like, of course I'm gonna come. Like, I'm here for the weekend, Valentine's Day. We'll do whatever. So I go to. And he's like, can you record the performance for me in the audience? So I'm like, yeah, so give me your phone. So I take his phone and I'm sitting in the audience waiting for him to go on. I was like, this whole karate performance, I'm like, what's going on? He's breaking things with his head. I'm like, okay, but if you love it, no problem. But I just. The music wasn't working. I don't know, it was like, meant to be. Like, the whole show was just delayed. And I'm sitting in the audience with his phone, like, Waiting to record it. And I'm like. So I go through his phone, and I'm like, oh, there's no girls. I thank God. But it's always with the boys. Him and his conversation with the boys. And he's just, like, texting his friend. He's like, I feel horrible. She flew here. And I, like, did this with the so and so. And, like, I just feel horrible. Like, this is not good, bro. What do I do? Kind of thing. And I was just so heartbroken because I already flew all the way this. This long of a way.

[Anna Kai]

When you're in college, you have, like, no money to begin with, so a flight's very expensive, right?

[Caitlin Reagan]

Everything just. All the effort and just the idea of, like, hurting so bad that, like, somebody was so convinced of something that just simply wasn't your.

[Anna Kai]

Wasn't your. Yeah.

[Caitlin Reagan]

So I'm like, now what do I do? I'm in New York, you know, I just did all this. He's cheated. I'm sitting in the audience. He's about to go break bricks with his head. Like, what am I doing here? So I'm like, you know what? Let me wait.

[Anna Kai]

Should have thrown a brick at him.

[Caitlin Reagan]

Literally. Literally. So I'm like, let me wait for the performance to be over. He does it, and I go backstage, and he's like, did you get it on the camera? I said, no. Hand him his phone. I was like, I don't even know what I said. Something. Something like, I'm gonna go home.

[Anna Kai]

Yeah.

[Caitlin Reagan]

And he knew. He was. I didn't do anything. I'm like, I didn't even say anything, like, right away. Yeah. So he ended up telling me that he just told his boys that he cheated to look cool. So I left the relationship with no closure at all and just trusting my gut that that was not the truth, that he definitely did cheat.

[Anna Kai]

Either way, it's bad. No, it's like, either way sucks. By the way, you don't look like a better person if you lied about cheating versus. Yeah. Yeah.

[Caitlin Reagan]

So we broke up. A year goes by, and it was hard to, like, kind of move forward from that breakup without. Because he was, like, saying, like, all right, if you leave this relationship, that's on you for thinking, you know, leaving for a lie. So really tried as hard as a gaslight the situation.

[Anna Kai]

So, dude, not cool because you were the one who fucked up. Don't put this on me.

[Caitlin Reagan]

I know. It was really. He didn't do the right thing by me, you know, at all. And a year goes by, and he Calls me. He's like, hey, I would love to meet up. I heard you're home for the holidays, you know, from Florida. In person, if. If you're okay with that. And I'm like, finally, I'm getting that. I'm sorry. Because they always come back. I always do. I'm like, this is perfect. And when I got in the car to meet up with him, he just looked different, and I didn't really understand why. And this is when he was like, listen, this is crazy. I. I don't even know what this means, but I'm just letting you know. I got diagnosed with cancer. Took his hat off. He was bald. He said, if there's anything that I do, because I don't know what's going to happen to me, I'll never forget this. I just want to let you know that I did cheat on you and I'm sorry. Like, that was like his. Like.

[Anna Kai]

Yeah.

[Caitlin Reagan]

I need to make sure, like, if. If I pass that we're at least okay, you know, that you got that.

[Anna Kai]

It's almost like he was like, you know what? I need to give you closure.

[Caitlin Reagan]

Yeah. And from there, that version of him, he just. He just grew so much. I mean, not completely. It could really make you into. You really get what life's about, you know? And it really just shaped him. And we didn't get into a relationship till years after. I always wonder, like, if he did not get cancer, if we would have ever been together. Cause, like. Because it really changed him to be such a beautiful person. Which sucks that it took for that. And I also always wonder, like, could he have gotten there without this? Perhaps, you know, but we just. We grew up and I got home from college and we gave it another go and it just. It just clicked and it just worked. And we were finally aligned and had similar morals. And that was when we started, just for fun. Tick tock on social media.

[Anna Kai]

Right? What year was this?

[Caitlin Reagan]

2020 for Covid. Yeah. So we just started making funny videos, just like an Italian Brooklyn couple just being funny. And then. Then he got re diagnosed and so.

[Anna Kai]

He was in remission at that time.

[Caitlin Reagan]

He was technically in remission. But the reality is it's. It's always one of those things that for him at least, because, like, he. He was in remission, but like, not entirely. He was like floating right on the tippy top.

[Anna Kai]

Okay.

[Caitlin Reagan]

It was always like a life that you just need to, like, it's. It's a change of life, so you need to make sure you're eating properly. And like you don't want to activate anything and like you're very cautious. And he's not drinking, doctor, you know, visits. And so it was always like a part of his life and my life while being with him, but it was sustainable. So we could still do everything that we wanted to do as young 23 and 24 year olds, travel, he would just bring his medicine with him. You know, he really tried to fit in, didn't want anyone to know he was struggling with this, just didn't want sympathy, didn't want to talk about it.

[Anna Kai]

He just wanted to live his life.

[Caitlin Reagan]

Just live his life and be happy.

[Anna Kai]

When you got into a relationship with him, were you thinking, like, he's going to beat this, he's young. Or was there always in the back of your head he might not make it?

[Caitlin Reagan]

When it was like sustainable and like we were like living our normal lives knowing that he had it and he knowing that he had it. I think deep, deep down it was like, well, I hope that wouldn't happen, but can't. Like no way. Like look at our lives. Like we're like a famous TikTok couple, we're in la, walking carpets. Like there's no way like that. It's almost like you said with my brother, like invincibility, like dying just doesn't sound like a possibility. Like that's not on the table, that's.

[Anna Kai]

Not on the table and you're just living like, yeah, yeah.

[Caitlin Reagan]

And so when we did do our LA trip in back right before, he got re not necessarily rediagnosed because he was always had this cancer, but when we found out that it spread because it started as testicular cancer, we were in LA for a big work trip and he was like, my back is killing me. And I was like, it's from the gym. And he was like, I hope so. And I just could tell that he was worried because I think he recognized the pain that I can't even understand to this day what that means, but he felt like something similar to what he's had in the past. And he was like, yeah, I hope it's just from the gym. And I'm just always like, come on. Like, stop. Like, it's fine. We get home from LA and like one day he wakes up in the middle of the night, he's like, this pain is horrible. Like, I gotta go to the hospital. Like, I can't sleep, I can't. He was trying so hard to hold it out, hoping this would go away one day, you know, it just wouldn't went to the hospital and they. They gave him scans, and we found out that the cancer out of nowhere, just spread in his liver and lungs and main organs. And that was, for me, the first day where I was like, could it be a possibility that we lose him? You know, like, is this it now?

[Anna Kai]

Yeah.

[Caitlin Reagan]

But when you have that thought, I feel like something like your survival mode pops you back into now. Can't be back into denial. And I faced that, like, maybe. Maybe not for a really long time.

[Anna Kai]

What's the process of saying goodbye, like.

[Caitlin Reagan]

At that age, after, like, so many months of, like, doing everything that they offered and doing outside research and don't. Trying our own things. There was one day, very close to a couple weeks after this, he passed. Where the doctors like, hey, like, we did everything we could. There's nothing more we could do. We could set you up at, like, hospice or. And for us, meaning me and his parents, we were like. And I was super involved as, like, a caretaker role. They don't know what they're talking about. We'll figure it out. Where the doctors now just really thinking that we were so deeply in denial. And I remember one day he sat us down. He's like, can you just stop, please?

[Anna Kai]

He had accepted it and everybody else hadn't.

[Caitlin Reagan]

He's like, just enjoy me. And for so two weeks, just going by on and on and on. And one day, I don't know what made me surrender, but we were just sitting down, and I just saw how much pain he was in. And he could no longer lay in the bed. He was like. Like, scrunched over. Like, couldn't even sit up anymore. And I sat down on the floor, and he was scrunched over, and I was just looking up at him, and I was. He was just, like. I just knew, Like, I. I don't. I don't know how to explain. I was like, okay, like, this is it. So, like, I'm done playing this game of what can we do? And trying to give him. Have nurses come in to give him my miracle vitamin C. Let's just. I just want to tell you I love you, you know? And, like, it just started, like, this whole chain of, like, here's what I want you to know. And it was kind of interesting because even, like, with the cheating came up and, like, how much, like, he. He learned, like, it was just so much stuff that feels like the biggest deal, like, even, like, past fights that we would have that we were laughing about in that moment, because it's like, that was so Stupid, like, true real life conversations that by the time that he took his last breath, I feel like it's just so nice when two people, like, have peace with it, and it just. When he's gone, you're like, okay. Cuz like, when you watch somebody suffer, like, the way that he did, like, nothing's worse than that. Like, hopefully there's something better than this because he just can't. It's not sustainable for him.

[Anna Kai]

Yeah.

[Caitlin Reagan]

It was almost like a. A sense of peace for everybody.

[Anna Kai]

Because you're like, he's no longer in pain.

[Caitlin Reagan]

Yeah. It was so bad to pain.

[Anna Kai]

And you've talked about this publicly, and you and I have talked about that, but Francesco has shown up for you in so many different ways since he's physically passed. But I think one of my favorite videos of you had a horse race and you were like, don't even. And that, like, gave me chills because. So for those of you who haven't watched this video, Caitlin was. And correct me if I'm wrong, at a horse race. And there was a horse that you bet on named Francesco. Cause you were like, oh, my God, the horse is named Francesco. And he was the slowest horse. And he was, like, last place.

[Caitlin Reagan]

Last. Like, not even last, like, in the back. Like, not even in the race.

[Anna Kai]

Not even in the race. And you were saying, oh, that's so on brand for you, Francesco. Cause he was always late, though, you know, Human Francesco was always late. And as soon as you said that.

[Caitlin Reagan]

The horse just, like, jets, like, goes through all the other horses and wins, and like, we were just, like. It was just crazy, too. Cause whenever I would, like, tell him in person, you're so slow, he'd get all, like, pride and ego, like, oh, yeah, watch this. And all of a sudden, man's moving, like, 100 miles per hour. So I'm like, oh, that's how it's gonna be, huh? So it just felt like the same thing through a horse. I can't say that. I'm sorry.

[Anna Kai]

You can't tell me that that's coincidence. I just. I refuse to believe that's so wild.

[Caitlin Reagan]

Also, it's like, all the other horses names were, like, not human names, let alone, like, you said, Francesco is not a name you hear.

[Anna Kai]

It's like Sparky. Sparky the horse.

[Caitlin Reagan]

Sparky, Pinky, Francesco. What? So I was like, wait a minute. An Italian horse?

[Anna Kai]

I didn't. The Italian Stallion.

[Caitlin Reagan]

Literally. What are we talking about here? So it just. It was really crazy. Really?

[Anna Kai]

That's wild. Have there been other Instances like that where he's shown up.

[Caitlin Reagan]

I think my second favorite one is that when he was here and I was at his house, I'd have my straighteners, my curling irons, and I would always leave them turned on by accident before we'd leave. And he'd be like, you're gonna burn the house down and rip the thing out of the outlet.

[Anna Kai]

Right?

[Caitlin Reagan]

So I have this system now. When I get ready to go out, I do my. No, no, no. I turn the straightener on so we can heat up. I leave it in wherever it is that I put it in, and I go downstairs, I pick an outfit. During that time, I come back up, my outfit's on, and I do my hair, so I turn my straightener on, and I leave it somewhere, and I go downstairs. Nobody's in my house. And the long story short is that when I came back up, it was turned off. It was weird. Like, I. I thought this through. Is. This has been an ongoing discussion in my head. I'm. I'm like, maybe I'm like, no, no, no. Like, I know I turned this on. Not only was it turned off, but it was, like, moved a little bit. Like, in a. In a place that, like, would not go on fire. Like, I don't remember the specifics. If you asked me the story, like, a year ago, I would have it better for you. But it was just, like, the way that I left it. Like, the house could have went on fire, and it just. When I acknowledged that it was turned off, I, like, looked up, and I just started dying of laughter, like, the same way I would when, like, he would yell at me in person. And, like, you just know that was him.

[Anna Kai]

He was like, girl, come on. You are gonna burn this house down.

[Caitlin Reagan]

Sometimes I tell you, you look straight.

[Anna Kai]

Fire, but you are also gonna cause a fire.

[Caitlin Reagan]

Yes. Literally.

[Anna Kai]

What is your relationship with your faith, spirituality, whatever you want to call it, like, since Francesco's past?

[Caitlin Reagan]

Oh, I love this question, because I'm on this journey right now. So when he first passed, I hated church. I hated God. I just, like, lost hope in everything because I'm like, there's just no way. There's something beautiful after this or somebody out there that's beautiful. When I lost him, he was such a good per. Like, why? And then after a while, you surrender, because holding hate in your heart does nothing for you. It's not a good feeling. And now I'm on, actually a current journey of finding God again. I go to church every Sunday. I have my little Bible that I read. So I'm Catholic, and I just want to keep growing that and just finding faith again. Truly.

[Anna Kai]

That's awesome.

[Caitlin Reagan]

Yeah.

[Anna Kai]

I truly think that we're too stupid to be it, and I don't believe in coincidences. I've realized that, like, God has shown up for me and so many times. I can't deny the timing of my life. Well, so you go every Sunday?

[Caitlin Reagan]

Every Sunday.

[Anna Kai]

That's amazing.

[Caitlin Reagan]

I've been trying. I mean, there's. Of course, there's some days that I'll miss if I have a night out. Sometimes I get a little hungover.

[Anna Kai]

Okay.

[Caitlin Reagan]

I'm like, no, not the Sunday mass. The morning can't get up.

[Anna Kai]

Do you go with you with family or do you go alone?

[Caitlin Reagan]

I actually go with Mr. Miro. He's on this journey with me. So that's amazing. We're both Franchesco's best friend. For context.

[Anna Kai]

You recently started dating again.

[Caitlin Reagan]

I did.

[Anna Kai]

How do you date again after that? And you're still so close with this family.

[Caitlin Reagan]

Yeah. So it's a very complex journey. First things first is not rushing into dating again. So I took a really long time, two years, just, like, learning about myself and, like, trying to re identify who I am, because I think Francesca was my purpose while he was here for so long, especially when he was sick, that it was very important to, like, understand, like, who am I? Because, like, if I don't know who I am, I can't show up for somebody else or a date or anything like that. But I think that what I really. When I really knew that I was ready to date again was. Was when I would finally come to terms with not feeling like I'm cheating on Francesco anymore. I think, like, when somebody passes on, like, you guys don't agree for it to be over, so it's like we're still together. It feels like. So how do I. How do I feel?

[Anna Kai]

You're like a widow almost.

[Caitlin Reagan]

So it's like, how do I not feel guilty? How do I not feel like I'm cheating? And I think that just comes with time and, like, understanding everything, talking it through. I had my podcast where I dive deep into everything that happened, which really helped me find peace. And then one day I woke up, I was like, you know what? Like, I want to give this a try, and if I don't like it, then I don't do it again for a little bit. And I figure out why I didn't like it and worked through it. But I just kind of woke up one day. I Was like, okay, let's. Let's do this. I think when you lose a significant other and, like, you. You go two years without dating, at a certain point, it's like, I'm gonna continue looping, like, where I am in life if I don't take this next step. And I think it was very important for me to date again, to, like, move forward with the grief and everything. So I just woke up one day. I was like, okay, let's give this a go. And I had a great first experience because the guy was really nice and understood kind of everything that I've been through.

[Anna Kai]

Are you still seeing him or was it just kind of like a, you know, I needed to do that, but he wasn't it kind of like, I.

[Caitlin Reagan]

Needed to do it. And I was. I felt deep down that it wasn't it, but I was a little bit, like, I'm just so proud that I did this. Like, I can't imagine and, like, trying this with somebody else. Let's just, like, stay put for a second and, like, understand what's going on. But he was just like, hey, listen, this was interesting too. I'm not really, like, into this whole social media thing, and it kind of freaks me out. And he's like, I just. I'm a very, like, quiet person, and, like, I just don't know if this is going to work. And I was like, that's actually very.

[Anna Kai]

Respectable that he said that to you up front.

[Caitlin Reagan]

Yeah, he was just like, you know, I know that you take people on your journey of life and, like, dating after grief, and it's just like, it's hard. Like, you know, it's just a lot. And I was like, that's okay.

[Anna Kai]

Yeah.

[Caitlin Reagan]

You know, but it was a little bit like, like, do I stop for a second? Like, is everybody gonna feel this way? And then I was like, no. Like, this is. This is what I do. And, like, it was. It was a good little wake up call because me and Francesco did social media together. And I was so used to a man being okay with this because, like, that's all we did together. So I was like, okay, I need to go into this remembering. Like, not everybody's like Francesco. Like, it's another thing, like, not comparing.

[Anna Kai]

You know, you're not trying to find Francesco 2.0.

[Caitlin Reagan]

No.

[Anna Kai]

Yeah, exactly.

[Caitlin Reagan]

And that's unfair. And that's another thing that goes into waiting before dating.

[Anna Kai]

Right. So you're not constantly comparing to, well, Francesca would have done this or he would have done that, or he would have helped me Film content. I never dated when I was in the public eyes. By the time I went viral, I was already basically married. And so we kind of figured it out together. Whereas I think it's interesting because I would imagine a lot of men are probably scared that, you know, if it doesn't work out, like, blast you, which is not your brand. And I noticed this when you were talking with your hands. You wear a ring on your left finger.

[Caitlin Reagan]

I know.

[Anna Kai]

And it looks like an engagement ring.

[Caitlin Reagan]

It does.

[Anna Kai]

Is there a story behind that? Or is it. You're like, no, I just like, this ring.

[Caitlin Reagan]

No. Yeah. Franchesco got me these two rings. And, yeah, I mean, they. They were promised rings. I definitely acknowledge that wearing it on my finger can give the wrong impression.

[Anna Kai]

Yes.

[Caitlin Reagan]

Right.

[Anna Kai]

You're probably not going to get picked up at a bar anytime soon, so.

[Caitlin Reagan]

Funny you say it like my. I just went out with my friend the other day. She's like, you're not going to get picked up at a bar. And I'm like, wait, like, is that true? And, like, yeah. And like, it's kind of interesting, though, because, like, with that being said, I still am like, but I still want to wear this ring right now. So I'm just trying to, like, give myself grace because, like, I'm just not ready to, like, do that. I don't know. I don't know why.

[Anna Kai]

That's fine. Yeah, that's also great, by the way, that you're like, you know what? I am not ready. And I'm not going to force myself to be ready for the sake of anyone else.

[Caitlin Reagan]

And it's also, like, if it does stop somebody from coming up to me, like, totally respect it.

[Anna Kai]

Right.

[Caitlin Reagan]

Maybe somebody comes up to me and doesn't recognize it right away. And while we're already talking, if he asks, I can explain. And that has happened and we still move forward for a day, and it went amazing. You know, I just feel like what's meant to be will be. I just think that, like, this is where I'm at and, like, this is me being authentic to, like, where I'm at in my life. So, like, what's meant to be for me will, like, come, you know, and.

[Anna Kai]

Some people, to be fair, like, not everyone notices because depending on the bar and everything I've had met, like, I've been on bachelorette parties since getting married or engaged. And, like, they don't notice because it's dark and you're holding a drink. And then they. And then I always have to be like, I'm you know, I'm sorry. I know. You know, you're not just asking me to hang, like, talking to me to be a friend. I'm married, you know, but, like, you can then have the conversation where if they come up to you because they don't notice the ring that, like, hey, by the way, I'm fully single, but this happened to me.

[Caitlin Reagan]

Yeah.

[Anna Kai]

You had a video recently that I absolutely loved. Cause you were like. I just had this epiphany where you're like, I used to be so worried about fitting into everyone else's life.

[Caitlin Reagan]

Yeah.

[Anna Kai]

And I think obviously we've talked so much about your childhood and, like, your trauma. It's like you were trying to fit into your dad's life. You know, you were trying to fit into this idea of what your mom thought you should be doing. And you were like, I just realized, like, you know, this was not an ego thing. It was no hate. I wanted to see this guy. He was so busy. He was like, let me see where I can fit you into my schedule. And you were like, you know what? I looked at my schedule, and I can't fit him into mine. I was like, you know what? Don't bother. That is so cool. That is so cool that you're like, I'm too busy to see you, you know, this week. So, like, let's not even try.

[Caitlin Reagan]

Don't you worry. Yeah, yeah. Don't worry.

[Anna Kai]

And I still think this is the case. So often we're kind of just waiting to be picked.

[Caitlin Reagan]

Right.

[Anna Kai]

You know? And you're like.

[Caitlin Reagan]

Which, by the way, because I. I have, like, a similar sometimes vibe. Like, in that video.

[Anna Kai]

It's more like empowerment.

[Caitlin Reagan]

Yes. Empowered woman. And, like, the guys attacked me. Like you were saying, like, I got. What's up with. Why are they so mad when, like, a woman, like, shows up and says, like, hey, I'm busy? They're just like, no, you're not. Like, what can you be busy doing? Getting a coffee? I'm like, wow. Like, it's so.

[Anna Kai]

Hey, if you could make money getting a coffee, wouldn't you, too?

[Caitlin Reagan]

Yeah, right.

[Anna Kai]

No. It's so funny because I never thought I was a controversial person when I first started making. I was like, I'm just empowering women because this is. I felt disempowered, and I felt disenfranchised for so much of my life. But I think what it is is, like, there is a subsect of very insecure men in real life where they feel empowered online because there's the anonymity of it. And they think by tearing you and me down that they will find their empowerment. Right? They're angry because they could never get you. You wouldn't even want to fit these men into your schedule, girl. You're right.

[Caitlin Reagan]

You're right.

[Anna Kai]

So that's what it is. It's like, you know what? I can't have it, so I'm going to reject. Maybe it's a little bit like what Francesco did when he first cheated on you. He was like, because I can't have her in the way I want to, I'm gonna reject her first. It's just immaturity. And a lot of people are like that, and they feel like that's how they can deal with the hate and the feelings of insecurity. But wait, did you ever see that guy? Did you. Did you guys figure out a schedule or.

[Caitlin Reagan]

Yeah, we did. I was like, wait, I feel like the bachelor of my life right now. Right? Yes, we did. And we had a great date. Watched the Knicks game.

[Anna Kai]

Oh, nice.

[Caitlin Reagan]

That's fantastic. Yeah, it was really fun.

[Anna Kai]

Will there be another date, you think?

[Caitlin Reagan]

Yeah, I'm still trying to figure out. Here's my thing. I'm in a place where I am dating, but I also am not really running for a relationship. I really would prefer to not be in one right now during this self discovery time. And I just wonder, okay, you get to the. The fifth date, it's like, what? Like, okay, how many dates are we gonna go on? Then it's like kind of like the conversation of like, is this going anywhere?

[Anna Kai]

So it doesn't have to be. It doesn't have to. Yeah, it could be anything you want it to be.

[Caitlin Reagan]

Okay. I just feel bad. I'm like. I'm like, am I wasting everybody's time?

[Anna Kai]

No. I mean, here's the thing is, it's like, I think we have to think about dating as the trial phase for marriage. If marriage is the end goal. Monogamy and traditional relationships. So I always think, like, you should not feel bad for dating. I mean, look, if you knew the answer, you should only feel guilty. If you were like, I don't like this guy. I don't want to date him, but I'm using him for something right now in my life because he feels a void or like, whatever. I just want to be taken out. Which, like, we know you can take yourself out. So we are all good there, right? I think you are allowed to explore. That's the dating phase. It's the exploratory phase. And I think we as a generation have become so non committal because, again, we're spoiled for choice. So we feel like we have to make the right choice because we have so many choices. But the thing is, you don't know what the right choice is until you figure it out, until you live it.

[Caitlin Reagan]

You're right.

[Anna Kai]

Right?

[Caitlin Reagan]

Yeah.

[Anna Kai]

So you're not wasting his time, because you don't know. You don't. You. You think, ideally you don't want a relationship right now, but you don't know. I mean, you could date him for another three months and realize, wait a second, like, I actually do want a relationship with you. I agree with that, you know, but you won't know until you get there. So many things have to be lived in order to be, you know, understood. You couldn't have known what. What would happen with Francesco in the beginning.

[Caitlin Reagan]

That's true.

[Anna Kai]

So you shouldn't feel guilty, because trust me, men do not feel guilty about taking their sweet ass time deciding whether they want to commit to women. Also, I think on a separate level, you should not assume that, like, he's pressuring you, you know, he's figuring it out too. You're getting to know each other. So I think when we try to jump too much into the future, it's like we forget to live in this moment, and the moment informs the future.

[Caitlin Reagan]

Were you dating more than one person ever at one time? Like, out putting yourself out there? Like, have you ever had a phase.

[Anna Kai]

Like that in the introductory? I never had more than one relationship at a time. So when it got serious enough to be like, the. What are we talk?

[Caitlin Reagan]

Okay.

[Anna Kai]

But I would date multiple men. Like, the first three to five dates, all at the same. I mean, I was crazy. Yeah.

[Caitlin Reagan]

I feel crazy. I'm like, what am I to bachelorette? Oh, yeah.

[Anna Kai]

No, it's like, you. And you know what? I'm so glad I did that. Like, I was. I had moments in my 20s where I was going on, like, three new dates a week. Thursday, Friday, Saturday, New guy, new guy, new guy.

[Caitlin Reagan]

Gotcha.

[Anna Kai]

And, you know, it gets exhausting, but it's like at some point you stop or you, you know, recalibrate, or you find the one guy that does break through the noise, the mo. When I met Dave, my husband, I had just gone out on a date with a guy that had asked me out. He was a client of mine, actually, and he'd asked me out after I rented him an apartment. And I was like, oh, this guy's, like, really cute. And, like, I had a really great connection and he was, like, very, like, witty and everything. And then. And then once I started dating Dave, it became very quickly apparent after about a month, that other relationship was like, I'm sorry, I can't. So when you know, you'll know, which is so, you know, overused. But if you.

[Caitlin Reagan]

That's true.

[Anna Kai]

If you can't decide between, like, three dudes, then none of them are. None of them.

[Caitlin Reagan]

Wow.

[Anna Kai]

None of them.

[Caitlin Reagan]

Very good to know.

[Anna Kai]

Right.

[Caitlin Reagan]

Advice.

[Anna Kai]

You will know. Just like you knew with, you know, when you said, I. I graduated from college, something had changed. I just knew. Yep, this is it. This is my person.

[Caitlin Reagan]

Yeah.

[Anna Kai]

Do you have, like, a rejection in particular that you always remember? And you're like, thank God that happened. Like, thank God I got rejected by this man or this business opportunity, or I didn't get this role because I wouldn't have the life I have right now if I had been accepted.

[Caitlin Reagan]

All right, so there's two things that come to mind. I would say one of them is definitely getting cheated on because, like, it really, like, taught both of us so much. But I would say the more important one is that going away to college. I wanted to go to Juilliard here for acting or just, like, any. There were so many at the time. Rutgers purchased Tisch.

[Anna Kai]

Anything like that.

[Caitlin Reagan]

Yeah, all, like, the acting schools. I got rejected from every single one because of my grades or my satisfaction and my last choice.

[Anna Kai]

Your SAT has nothing to do with how your ability to perform.

[Caitlin Reagan]

I literally don't even know why. Prep monologues, because, like, they're like, oh, sat. Sorry. I'm like, okay, then why am I here? But whatever. I FAU was my last choice. The college in Boca. I did not want to go to college in Florida. It's not known for acting. I'm like, I'm in New York. What am I doing? And my mom's like, look, you gotta go to college. Or, like, you go to, like, a community college by the house. And I was like, I guess I'll try Florida. It was scary. It's, you know, so far away, but that getting rejected from every college. I was crying. I was so miserable. I'm, like, downplaying, like, how horrible it felt. You know, it was the best thing that ever happened to me. Entirely shaped me. It showed me, like I said, that there's more than just, you know, there's more out there in life and just a different lifestyle, of finding myself, being on my own, like, navigating a new state and new people and just a whole new life. It really made me who I am today. Entirely so awesome.

[Anna Kai]

Yeah, I love that. Thank you so much for coming here today and sharing everything. Where can people find you on social Media?

[Caitlin Reagan]

All right, CaitlinReagan K A I t L I n underscore R e a G a N thank you so much for having me on here and you inspire me as much as you say I inspire you. So thank you so much for your videos.

[Francesco]

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