Jared Freid on His New Relationship, Brand-New Book, and More – Part 1 | Golden Hour

Summary

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Bachelor Happy Hour – Golden Hour: "Jared Freid on His New Relationship, Brand-New Book, and More – Part 1" (June 2, 2026)

Episode Overview

This lively episode of Bachelor Happy Hour (Golden Hour) features comedian, podcaster, and Bachelor Nation favorite Jared Freid. Joining hosts Susan and Kathy, Jared opens up about his new relationship, his just-released dating advice book Walking Red Flag, and a range of topics from the economics of singlehood (“the single tax”) to navigating midlife love, vulnerability, and personal growth. The episode balances humor, relatable life lessons, and candid conversation—offering a backstage pass to the emotional and financial realities behind modern dating.

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Main Discussion Topics & Key Insights

1. Jared’s New Relationship: The Real Story

• Background: Jared reveals he’s now in a committed relationship after reconnecting with someone he previously dated. He shares why their story is not a fairytale, but a lucky, “messy” outlier.
  • “We actually dated, and then I ended it, and then we got back together…My story’s a warning. My story isn’t…an inspiration for others. My story's a warning. You’re lucky, you know?” — Jared (09:08)
• How They Reconnected: After more than two years without communication, his now-girlfriend reached out after seeing promotions for his show.
  • "She was braver than I was… I had been thinking about her over the years, and then I got a text from her." — Jared (09:23)
• Family Reactions: Jared jokes about his mother’s approval and the lack of dramatic family drama.
  • “She loves her. So that's like a problem for me? I have nothing interesting to say about it. I wish.” — Jared (12:13)
• Age Gap and Dynamics: Jared is 41, his girlfriend 32; he jokes about being into older women, but then he shares how being older brings clarity and maturity to the relationship.
  • “The beauty of waiting till you're 41 to get into a very serious relationship is that…I've already had these arguments with other people.” — Jared (21:39)

Timestamp: 04:52–12:33, 25:00–25:23

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2. The “Single Tax” and Financial Realities of Dating

• Defining the Single Tax: Susan introduces the concept as the higher per-person cost singles pay for things like rent and subscriptions, since couples can share expenses.
  • “It's a higher cost of living and financial burdens that single adults face compared to couples or families.” — Susan (13:10)
• Emotional Economics of Singlehood: Jared shares candidly about the comfort (and cost) of single life, and how that security can make it hard to risk coupling.
  • “You're paying a premium for your freedom... You become more precious about ruining that when you go into the next phase.” — Jared (14:19)
  • "A lot of people are single...living with bronze handcuffs, not even golden handcuffs. 'I'm getting by. I like my life. I'm happy enough. Why would I risk happy enough for probably miserable?'" — Jared (14:31)
• Financial Conversations in Relationships: With playful honesty, Jared describes negotiating logistical things like splitting bills, clearing closet space, and affording a shared life as “fun decisions” made easier by age and experience.
  • “It's more of, like, to me, it's a fun decision on how to do life.” — Jared (22:54)
  • “At 41…I've already had these arguments with other people. She shouldn't have to deal with these things, you know?” — Jared (21:39)

Timestamp: 13:06–15:11, 21:02–24:08

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3. Relationships: Readiness, Change, and Growth

• Why Commitment is Hard: Jared admits to repeatedly ending relationships before they could get serious, rooted in fear and lack of confidence more than actual issues.
  • “I'm the dumper. I would dump people before the next step because I wasn't confident enough to go through the next step.” — Jared (31:41)
• On Real-Life Change versus Advice:
  • “Advice: easy to give, tough to take…We can dish, but I had to be held to my own words…That was what made dating so hard for me.” — Jared (42:25)
• How Life Changes With a Relationship: He jokes about “less masturbation” (27:02) but reflects sincerely on shifting social spheres, travel, and how women’s friendships differ from men’s.
  • “Male friendship is a little easier…My friends, oh, what are you doing? Where are you? Who cares?” — Jared (27:17–27:39)
  • "Women go on trips together, and then they stay in the hotel room and then they talk about, you know, their lives together. There's just a different relationship." — Jared (27:41)

Timestamp: 24:08–28:50, 31:41–32:13, 42:25–43:39

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4. “Walking Red Flag”—Jared’s Dating Book

• Book Genesis: Jared’s new book, Walking Red Flag, is a collection of personal stories, a self-effacing look at dating trials from “getting dumped to getting dumped again.”
  • “It is a dating advice book. And it was really just personal stories about dating and how I felt throughout the whole process. It takes you from getting dumped to getting dumped again, because that's all I knew.” — Jared (29:29)
• Writing and Relationships Collide: He finished the book before getting back together with his girlfriend; she features in a few stories, demonstrating his lingering feelings.
  • “I wrote this book over the two years we hadn’t seen each other…and a couple of them had her in mind.” — Jared (32:13)
  • “She read it, and she's like, 'three stories. You did three stories?' And I was like, 'you're right, all three.'" — Jared (32:45)
• Life, Messiness, and No Instructions: Jared reiterates that no dating advice fits every situation, and that everyone’s story is unique.
  • “Life is messy…The consistent part was always that every situation is its own situation…Be a better buyer…consider your situation and go forth.” — Jared (35:30)

Timestamp: 28:55–36:32

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5. Body Image, Confidence, and Comedy

• Body Image & Social Pressures: Jared and Kathy discuss body image, confidence, and the pressures of social ideals. Jared acknowledges even “confident” comedians struggle behind the scenes.
  • “When you don’t feel good about your body, it is tough to go on that date, feel good. You skip things, you make rationalizations.” — Jared (44:10)
  • “People would think I'm the most confident person in the world. I don't care how someone—I don't care how loudly someone screams on the Internet about how confident they are. They're not.” — Jared (45:48)
• Culture and Social Media: The group notes a positive shift toward body diversity in media, but Jared remains skeptical of its impact on real-life confidence.

Timestamp: 43:50–46:51

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Notable Quotes & Fun Moments

• “The only person that will ever compare their mom to a finger…” — Jared, after a notorious digression (12:48)
• “It’s a lot less masturbation…you know, that [is] a huge change for me.” — Jared on how getting into a relationship changed his life (27:02)
• “Divorce is for the poor and the very rich.” — Jared reflecting on the financial trap of relationships (26:03)
• “Write a book about it. Wait for her or him to reach back out to you. And life will be fast.” — Kathy’s tongue-in-cheek PSA inspired by Jared’s real-life story (35:14)
• “Advice: easy to give, tough to take.” — Jared distilling the challenge of giving and living by your own relationship advice (42:32)
• “Fake it till you make it, babe.” — Susan on confidence and social pressures (46:13)

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Structure & Flow

0:00–4:16 – Ads and catching up
4:16–13:06 – Jared’s introduction, travel banter, and the beginning of relationship talk
13:06–21:02 – The “single tax” and economics of dating
21:02–25:23 – Moving in, money talks, age, and relationship dynamics
25:23–32:13 – Changing relationship status, book writing, and personal growth
32:13–36:32 – Book backstory, dedication, life is messy
36:32–42:25 – Ad breaks
42:25–46:51 – Advice, honesty, and body image
46:51–49:26 – Closing questions about dating history and careers
49:26–52:39 – Outro and ads

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Takeaways for Listeners

• Relationships rarely go “by the book”—messiness is part of the journey.
• There’s no formula for when or why things finally “click”; readiness is personal, not prescriptive.
• The hidden economic and emotional costs of being single are real, but so are the challenges of coupling.
• Personal growth and honesty—whether in podcasts or books—drive real change.
• Humor, vulnerability, and self-deprecating honesty offer healing (and some great stories) for everyone navigating love.

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Tune in to Part 2 next week for more with Jared Freid!

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Transcript

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[Kathy]

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[Susan]

Welcome back to Golden Hour. Hi, I'm Susan.

[Kathy]

And I'm Kathy. How are you doing, Susan?

[Susan]

I'm doing great. I'm jealous you're still in Portugal and I'm not there yet.

[Kathy]

I still am in Portugal. And you know what? We have such a special guest this week and if it doesn't work out with him, I'm hanging out at the Ferrari dealer. So let's introduce our special guest because you know, I am a quarter of a mile from the Ferrari dealer. Okay. We have a really special guest this week. Comedian and bachelor, live screamer. A man who I adore, Jared. Hey, Jared, how are you?

[Jared]

So good to be here with you guys. Obrado, Kathy and oh my God, he knows.

[Kathy]

Obra Godo.

[Jared]

I mean I listen, you both look amazing. Kathy, you, you're, you're glowing. You have your very much Kathy got her groove back European vacation vibe. I can Feel it. You're having spritzes in a piazza. This is just. And Susan, a little blonde in your hair, going a long way. You look amazing. I love it. Love it.

[Susan]

You're in Florida.

[Kathy]

You're looking mighty happy.

[Jared]

Thank you. I'm in Florida. Yes. Delray Beach.

[Susan]

Oh, in Delray.

[Dietz and Watson Advertiser]

I was in Miami last night.

[Jared]

Oh. And last night. Look at Susan, just hopscotching across this great nation of ours. Just Miami knights, New York days. Oh, my. You guys are really women of the world. It's really great to be here.

[Kathy]

Wait, do you live in Delray?

[Jared]

I live in Delray.

[Susan]

Yeah.

[Dietz and Watson Advertiser]

I don't think I knew that.

[Jared]

Okay, I forgot to call you. I should have called you and let you know.

[Susan]

So can we just, like, jump ahead just for a second? Let's jump ahead because Kathy told me a little something about you. First of all, you look fabulous. Did you lose weight? Like, you're all cut now. Their face is looking good.

[Jared]

They have this new drug called Ecstasy. And what's her real name? I'm taking the boomer ecstasy. GLP1. I.

[Susan]

Well, it shows how much weight have you. Really good.

[Jared]

I. I don't live my life by the scale. I live my life, you know, one. One cheeseburger at a time. And I. No, I. I think I lost ten pounds. But, you know, when you live by the beach, it changes your old demeanor. You know, this. You get it? You're looking right now, you're out in Lisbon. You're looking at the sea. We just saw you chase away a young Portuguese man to get out of your room. Before we taped, I just saw a guy. He was wearing Speedo cut underwear. Very European. Kathy, you get it?

[Kathy]

No.

[Susan]

He ran because she pulled the suitcase

[Jared]

up a mile hill.

[Susan]

She's nuts.

[Kathy]

No, Jared, I'm just gonna say, don't

[Jared]

wear your heels in Lisbon. I've been.

[Kathy]

Jared, let me just tell you, in Lisbon, it's all hills.

[Jared]

I. I know. I've been. I. I literally, I, I. Lisbon was beautiful. I loved it. Don't go to Camparda. Horrible. Not worth it.

[Kathy]

Okay.

[Jared]

Not a great beach town. Lisbon was awesome. The food was great. The people were wonderful. Very much a laid back surfer vibe in Lisbon. Very laid back. I. Kathy, I. You couldn't be more the opposite of the people of Lisbon. I. I'm just imagining a guy on one. I'm just imagining Cathy yelling at one of those people with one of those tiny. What are they called? Shooks. What are the. What are the Speedos? The Tuk tuks, The Tuk tuks are these little tiny cars, and the guys who drive them, they're like, hey, you need a ride? I'm just imagining Kathy. I need a seatbelt back here. There's no seat belts back here, Jared.

[Kathy]

Jared, I'm just. Susan is going to start this off because we want to talk to you about the single tax. I am, first of all, exceedingly single here in Lisbon. Exceedingly single. And I just want to say, even though I'm in Lisbon hunting for a Portuguese man who I don't speak a word of Portuguese except abregado. Abregado. I've learned that one. Here's the deal. You have broken my heart because you told me that you were into older women and I was going to be the one. So, Susan, why don't we just start on this single tax discussion, since he is.

[Susan]

He looks younger to me, too.

[Jared]

I mean, I've gotten younger. I keep getting younger. I use skin cream now. Listen, you get a girlfriend, you start using her products.

[Susan]

GP1. What is it?

[Jared]

GLP1.

[Kathy]

GLP1.

[Jared]

I call it Chubby Medication.

[Kathy]

Jared.

[Jared]

Yeah.

[Kathy]

We're just jumping ahead here. I'm going off script.

[Jared]

Okay.

[Kathy]

How long have you been dating her and when did you meet her? What does she look like? What does she do? I want all the details.

[Jared]

So she's. She's in wealth management. She's a sugar mama. I'm got my. My mortgage taken care of now.

[Kathy]

Okay.

[Jared]

Rich woman who wealth manages. And she's. She. We go way back, actually. We actually dated, and then I ended it, and then we got back together. And so it's one of those stories that I wouldn't tell someone can happen to them. Like, you know, the worst thing that people in relationships do is try to make their story somehow an inspiration for others. My story is probably not an inspiration for others. My story's a warning. My story isn't. You're lucky. You know, what people should be, you know? Right. I mean, like, I feel lucky that she and I were in the same space to be able to want to give it a shot. And I feel lucky that it worked out the way it has, but also, like, to count on this being, you know, for other people. We. We were. We didn't talk for two and a half years and then came back into each other's lives. And she reached out, she texted me. She was braver than I was. I had been thinking about her and over the years, and. And then I got a text. I was going to Philly for a show and I was like, should I do it? Should I not? Should I text? Should I not? And then I got a text from her like, hey, your sponsored ads for your show keep coming up. Want to get coffee?

[Kathy]

Is she in Philly?

[Jared]

Yeah, she was. Is she living with you now, moving down here?

[Susan]

Is that why I didn't get the call that you were in Philly? Like, Kathy gets the call, you're in Austria. Well, I could have went sat next to her. We could have been friends, you know?

[Jared]

I know. Well, she didn't come to the show. I was like, I had the show. I was like, let's wait. I'm not going to, like, you know, we got coffee the night after day after my show and just caught up. And, you know, it was like, I just had like a body feeling where I was like, this is. You know, it was a little bit like this person's happy and just a breath of fresh air. And then also like, you know, don't, you know, don't with this person, you know? You know, it's kind of like, you know, if you're going to do this, do this, but don't mess with it, you know? So I. I think that's why I was so afraid to text, because I was like, I knew that, you know, you have. There's a part with dating where you have the information you need, and it's like, okay, am I ready to do that next thing? Go over that next hump? Considering there's a point where it's like, what else do you need to know? You know, so. And I was. I'm definitely one of those people that puts off decisions with everything. I don't want to hear the answer. Two years, right? Two years. Well, even before that, when we dated you, I was. We got to the point of like, hey, what's the next thing? And it's like, you either keep going, doing something that's below, you know, makes everyone feel uncomfortable and not a real relationship, or you push through to the next thing. And I just didn't have the confidence then, you know. Okay, I still don't.

[Kathy]

I gotta interrupt you.

[Jared]

Yeah.

[Kathy]

We are of the same tribe. Last time we were talking about your mom and your mother's like, if you found a nice girl, I'd be. First of all, is your mother happy?

[Jared]

She's very happy. She's great.

[Susan]

She likes her.

[Jared]

In the beginning, I, you know, it'd be more fun stories if she hated her then now she likes her. So she loves her. So that's like a problem, you know, for Me? I have nothing interesting to say about it. I wish. You know, my mom's a pain in the ass at some point.

[Kathy]

Don't say that.

[Jared]

That she's a pain in the ass. It's the truth. What, do you want me to lie?

[Susan]

It doesn't mean he doesn't love.

[Jared]

Right. Jared, you can be a pain in the ass and also love it. Like, that's it. Right. I've gotten a finger in the butt during a blowjob. Like, that's. I love that. And it's a pain in the ass.

[Susan]

Literally.

[Kathy]

So, okay.

[Jared]

The only person that will ever compare their mom to a finger.

[Kathy]

Will you please? Because this is a perfect segue.

[Jared]

I just come on here to make Susan laugh and. Kathy.

[Susan]

God, I can't catch my breath. Wait, wait. Jarrett, we are going to talk about something today, and it's called the single tax.

[Jared]

What is the single tax?

[Susan]

Okay.

[Jared]

Which life costs more when you're single?

[Susan]

Exactly. It's a higher cost of living and financial burdens that single adults face compared to couples or families. I mean, when you're in that, they split it. Right. It refers to the lack of shared expenses for rent, utilities, and subscriptions rather than a literal government tax.

[Jared]

I think the single tax is a wonderful discussion point for why people stay single, too. You know, like I. And why I was so afraid of moving into the next level of life. I. And I think a lot of people who are single, once you get to a point where you can take care of the cost of your life.

[CeraVe Advertiser / Product Promoter]

Yeah.

[Jared]

Then you get comfortable and you're like, I'm not going to bring in someone who could ruin this. So, yeah. You know, you're paying a premium for your freedom. Freedom, Right. So you could look at. I'm an economics major. Kathy. I know you're an economics person yourself. So I was. The single tax speaks. I love the meshing of dating relationships and. And the economics of it, because I do think that matters. When I was single, the only thing that could ruin my life was a woman. You know, I had my life set up. I could afford my life. I had my comfortable couch. I was able to go out anytime I wanted. And the only thing that could be brought in to ruin me, both emotionally and financially, was a woman. So it became. You become more precious because you're paying such a premium to be single. You become more precious at ruining that when you go into the next phase. So a lot of people are single. They're kind of like living with bronze handcuffs. Not even golden handcuffs. They're going, I'm getting by. I like my life. I'm happy enough. Why would I risk happy enough for probably miserable?

[Susan]

Yeah, but that's you. There's people out there that would but enjoy.

[Jared]

People out there say that. I think people out there who would would say, well that's, that's just me. Until they get to the point where you're on the precipice of like do I enter in a relationship? You go I don't want to. You know, to me, I'd rather pay the money to not deal with did

[CeraVe Advertiser]

you know you can hydrate your skin up to 10 layers deep with CeraVe facial moisturizing lotion?

[CeraVe Advertiser / Product Promoter]

Their AM facial moisturizing lotion SPF 50 provides SPF 50 protection and lightweight hydration

[CeraVe Advertiser]

that lasts and when it's time to wind down in your day with PM Facial Moisturizing Lotion that lasts through the night and has 48 hour hydration. Both contain three essential ceramides and MVE delivery technology to help strengthen the skin barrier in just one hour.

[CeraVe Advertiser / Product Promoter]

I love CeraVe. My dermatologist recommended it to me years ago and it works incredible on my skin. I love that the AM Facial Moisturizing lotion has SPF in it so I don't have to add an extra step to my routine.

[CeraVe Advertiser]

I also love the PM Moisturizing Lotion to help my skin recover and be restored at night. If you're looking to be hydrated all day, check out CeraVe.

[CeraVe Advertiser / Product Promoter]

It's developed with dermatologists and is fragrance free, paraben free and won't clog your pores.

[CeraVe Advertiser]

CeraVe is the number one dermatologist recommended facial moisturizer brand and offers a range of facial moisturizers for all skin types.

[CeraVe Advertiser / Product Promoter]

Find yours.

[Dietz and Watson Advertiser]

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[Kathy]

Here's the question, Jared. I need yes or nos here. This is. Let's keep it simple here.

[Jared]

Okay? Kathy. Kathy's never given a yes or no in her life, and she's asking for yes or no.

[Kathy]

Keep talking, Jared. Keep talking. Let's tell that. Is she paying half the rent? You know, are you going to give her any of the closet. How's it going to work here on this single?

[Jared]

I've cleared out a closet for her. I. She's gonna pay the whole rent, and I'm gonna, you know, make love to her. You know, in exchange for that, I'm gonna give her everything she needs physically, and she'll take care of us monetarily. No, I'm gonna.

[Susan]

I call you.

[Jared]

Those are discussions. You know, it's funny. We did. We did talk about the, the finance stuff. And like, it's. The. The difference is. So when you're afraid of entering in a relationship, you're like, I'm gonna avoid that conversation completely. When you're like, kind of when you're happy and ready to do it. That was like, so e. Like, to me, it's right. It's right. To me, it's like a negotiation. Let's figure it out. Like, I bought a place here in Delray and I'm like, I want you to feel like it's your place. I want it to be our place. Like, I want you to, like, come here and, like, feel like we're. We have a thing. And I'm saying that at 41, like, I, I don't think at 23, these conversations are as easy or as I'm. Or I'd be as thoughtful. So, like, the beauty of waiting till you're 41 to get into a very serious relationship is that, you know, I've already had these arguments with other people. She shouldn't have to deal with these things, you know, So I. I don't know. There's things that we're gonna have to deal with that I. That happened because I'm 41, and there's things that we, you know, I've already worked out. You know, like, it's. There's pros and cons to everything, you know, so she could do the food

[Susan]

shopping without asking for money.

[Jared]

Right. Well, that's the money thing, right? She.

[CeraVe Advertiser / Product Promoter]

I.

[Jared]

It's funny because, like, when we were talking about, like, how do we divvy up the expense or how we combine, it's more of, like, to me, it's a fun. It's a fun decision on how to do life. Like, it's not. This isn't as stressful to me. Like, I actually, I was like, oh, you're paying that in rent, and I'm paying this in a mortgage. Oh, we might have this money free to do this with it, or maybe we can go into an aggressive stock account, you know, like, whatever. Like, I don't know. Like, these are. And now I feel like. Like, these are, like, you know, I wish it was more. I. I don't know. I. I'm. I'm very. What's it called? I'm very. That seems fun to me more than it feels.

[Susan]

And because you're 41 and established and you can do it.

[Jared]

Right?

[CeraVe Advertiser / Product Promoter]

Right.

[Jared]

It's not like I'm, like, worried about my. I. I are not worried yet. Well, we'll see.

[Kathy]

I would say to you, Jared, a couple of things here. Buy low, sell high. There's some financial advice for you. Next question. Has your mother purchased the glasses for y' all to step on at the wedding?

[Jared]

Not yet. We. We're. We're a little bit far away from that. We'll get there. We look at glasses, you know, to step on. But we'll. We'll get there at some point. Point.

[Susan]

Do you talk about marriage or. Right now? She's.

[Jared]

Yeah, I think it's, like, a fact of life, you know, like the. Again, like, I have the information, you know, the toughest part for me was really to, like, say, go and. Well, being on a podcast and saying I have a girlfriend because I would be dating someone, and I was dating. Like, I wasn't I wasn't like, you know, being casual with people. I was. I was going on dates and having, you know, conversations with people when I was dating. And then it would get to a point where, like, okay, well, I go on a podcast and talk about how I'm single with someone who I'm, like, kind of close to not being single with. Like, it got uncomfortable. It's like I either have to lie here or lie to them or lie to both or feel like I'm playing a part, you know, that once that kind of got out of the way, which was tough for me.

[Kathy]

Yeah.

[Jared]

All that other stuff was kind of a little bit easier, you know?

[Kathy]

So I have a question, Jared. How. I don't know how old she is. Do you? We. Are you willing to share?

[Jared]

She's 82.

[Kathy]

No, seriously, come on.

[Jared]

I told you I liked older women. She's 82.

[Kathy]

She's a.

[Jared]

She's 32. She's 32.

[Kathy]

Okay, so. Okay, so here's my question. She's. She's a bit younger, but you're 41. How does that look different?

[Jared]

The sex? It's different. We, you know, I have to find a way to show up.

[Susan]

So let's talk about people that aren't as fortunate as you. And don't worry about splitting the bills, because a lot of people that are comfortable living together, do you think they stay together because financially they're not going to be as comfortable?

[Jared]

Well, that's. Well, this is the problem. You know, Like, I, you know, I'm not doing well enough to get a divorce. You know, I'm doing well enough to get in a relationship. I. But I can't get. I don't have enough money to get out of a relationship.

[Susan]

So, like, exactly.

[Jared]

You know, there. That. That's. I know a lot of people. I. I would say more people than would like to admit are financially not able to divorce. Divorce is for the poor and the very rich.

[Kathy]

Hold on here. You just entered into this relationship.

[Jared]

I'm just telling you the truth.

[Kathy]

We're gonna change the narration here. I want to know, and I'm being serious here, which I always am.

[Jared]

Always.

[Kathy]

How do you think your life, you know, you've been single, and you told me once not too long ago that with all your traveling and your, you know, your stand up, you do a lot of traveling, that you weren't really ready to enter into a relationship. So now I know, on top of everything else, you're a liar.

[Jared]

Total liar.

[Kathy]

But here's the thing. How is life? And I'm being serious, Jared. How is life going to change for you? Because you do travel on the road a lot. How is it going to your friends? I'm guessing, I don't know. Are most of your friends single couples? How is that good? That sphere going to change for you?

[Jared]

It's a lot less masturbation. You know, it's really. That Help himself a huge change for me. You know, I don't have to buy as much lotion. And I.

[Susan]

And when you go out, you're bringing somebody with you, right?

[Jared]

And so that's different. Set me up. I. I mean, first of all, my friend, you know, male friendship is a little easier, I think, because male friendship's not as depthy. Like, the way my life went wasn't. Yeah. Like, female friendship. You got Susan. You're going to Lisbon to go hang out.

[Susan]

No, I'm going to Italy, actually. She's in.

[Jared]

You're going to Italy? You know, like. But, like, women go on trips together, and then they stay in the hotel room and then they talk about, you know, their lives together. There's just a different relationship. I. My friends, oh, what are you doing? Where are you? Who cares? You know, how many people when I moved to Delray beach were, like, women? Every woman would ask me the same question, do you have any friends there? And I'd be like, friends? Who the fuck cares? What do you. What am I, 8? I'm going. I'm moving to a beach town. I'll figure it out. And I think that a lot of men feel that way where it's like, you know. You know, when I was single, it didn't matter to my friends. And when it. When I got a relationship, oh, bring her in. You know, like, men, you know, the only one was their wives. They'd be like, oh, we. You know, I. You know, because when I dated Emily before, my good friend, you know, his wife was like, I really liked. You know, would always bring her up. And I'm like, oh, they could be buddies again, right? Well, she was so happy when we got back together. She was like, I can. You know, I really liked her. And I was like, boy, no one else really was affected. You know, my friend was like, whatever. You do, you do, we'll figure that's how men are.

[Susan]

What did she. Please tell me. She said these words. It took you long enough.

[Jared]

Well, I. Actually, the. Here's the crazy part. I wrote a book, so I, I, you know, you could be like, well, Jared, you're just saying these things because it's easy to Say now that you were thinking of her. Well, I actually have a book that comes out that you can pre order now. It's called Walking. Red flag. It is about. It is a dating advice book.

[Kathy]

Excuse me, can you send us signed copies? I'm not paying.

[Jared]

Always looking for something free. It's always. I'll send you guys a copy. I'll send you a copy. It's called Walking.

[Susan]

I need to read it.

[Jared]

And it's a dating advice book. And it was really just personal stories about dating and how I felt throughout the whole process. It takes you from getting dumped to getting dumped again. Because that's all I knew was. I only knew how to do, like a year in a relationship and this is all this is about. So you get dumped and what do you do? How do you figure it out tomorrow? Okay, I'll send it out today. I'll send you both copies.

[Susan]

So tell me. Tell me one key word, please. What was that? Trigger. What made you change all this?

[Jared]

Well, the. The opening page is like a story about growing up. The. The opening page of the book is about. I was 13 years old and I remember I was like, I'm gonna call this girl to be my girlfriend. Because I was like, everyone's got a girlfriend. I gotta have a girlfriend. I remember going in the phone book and finding her number and then going on the second line. Like, this is like. I'm literally like, all these are words that people wouldn't understand. I go on the second line and I pick up the phone quietly. Like, I'm like, not even allowed to use the phone in my house. And I'm sneaking and I call the girl and all of a sudden my mom picks up. The second line is like, hello, Jared, Why are you on the phone? What are you doing on the phone? And I'm like, shaking. And I take the phone and I throw it across the room and I just run. I run away. I, I, I, I. And I end up not calling her to be my girlfriend. It's like, it's such a butterfly effect moment. Like, what if I had asked her to be my girlfriend? She said yes, and now I'm like, cool guy with a girlfriend. I wouldn't even be a comedian. I wouldn't be the sad loser who goes on stage and talks about his body issues. Maybe I'd be a cool guy and a lawyer. Like, have a family already. Like, this is a huge moment of my life. And my mom kept going, why are you on the phone? What are doing you are you doing on the phone? And I literally was, like, playing video games, acting like nothing had happened. And this is the opening page of the book.

[Kathy]

I love it.

[Jared]

And I always tell people from this, you know, what do you learn? Is that you should always try and.

[Kathy]

Okay, I have a question. Are you the dumpy in your life?

[Jared]

I'm the dumper. I. I would dump people before the next step because I wasn't confident enough to go through the next step.

[Susan]

What was that? Fear.

[Jared]

What?

[Susan]

That wasn't confidence. Obviously, you got the confidence, but you had the girls. You just dumped them.

[Jared]

Yeah, but confidence comes in different forms in different ways, you know, like, you know, some of you. Some people are confident enough to go on a first date and then not confident enough to have a family and kids. Like, I think that takes a different type of confidence or delusion. It's a mix of the two.

[Susan]

Or.

[Kathy]

Or they miss birth control.

[Jared]

One or the other. And then they rationalize, wow, well, we can do a kid. And you go, okay. You know, like, so I. I don't know. I just think I. I didn't even take my own advice, you know, Like, I didn't even try, you know, she took the advice without even reading the book. And then. So I wrote this book. Over the two years that we hadn't seen each other, I wrote this book, and I ended up writing all these stories out with regrets and how I would have done things differently. And a couple of them had her in mind, you know, And I proof

[Susan]

you were thinking about her, right?

[Jared]

And then. So did you dedicate it to her? No, because when she texted, it was already published. And she texted, and she was like, let's get coffee. And then we got coffee. And then we, like, started going on, you know, getting back together. And I was like, by the way, there's a book. And by the way, you. And she's like, let me read. And she reads it, and she's like, three stories. You did three stories? And I was like, you're right, all three. She remembered these specific moments that I was, like, hashing out, because really, it's a snapshot, this book, of, like, the two years in between and the dating I was doing. And, like. And then. So it is kind of interesting the way it, like, I don't know. I don't know if someone. If someone just had a relationship end and they think the person could come back. Like, just have that person write a book, you know, that's all there is. That's all you have to do.

[Susan]

Well, can I ask you a personal question? Were you really Falling in love with her to the years before. And you left because you were afraid. Yeah. Or you weren't ready, if you will.

[Jared]

I. I don't think I was ready.

[Kathy]

Before you answer was, did your fam. Had you met her family?

[Jared]

No.

[Kathy]

Had she.

[Jared]

She met.

[Kathy]

Had she met your family?

[Jared]

She met my brother and his wife before, in the first time we dated, and I didn't handle that as well as I would have liked to. I didn't take it as.

[Kathy]

How long did you date her the first time? How long?

[Jared]

Two months.

[Susan]

Oh.

[Jared]

Oh, yeah.

[Kathy]

Wow.

[Dietz and Watson Advertiser]

Wow.

[Jared]

Yeah. But the. You know, so.

[Susan]

Well, you know, she's the one now because it's on our podcast, right, Emily? I'm writing down.

[Jared]

Well, you can read about it in the book so that I can afford, you know, the. The house that we have. I know that. Walking Red Flag. You can pre order it. And I do the voice. I do the audiobook so you can hear my beautiful voice.

[Kathy]

Can I ask. Can I ask you a question? Jaron?

[Jared]

You're on a podcast. You can ask me anything.

[Susan]

Ask what?

[Kathy]

My question is, have you written a book lately? And if you have, what is the title? And how can I pre order.

[Jared]

Walk. I have. Thank you, Kathy. Walking Red Flag and just go on Amazon. You can just go. You can just go order it now. You can pre order. Actually, I'm going to beg the listeners pre order it because it gets me on the New York Times bestseller list. And I told my dad, I was like, there's a chance I get on the New York Times bestseller list. And my dad went, how you gonna do that? He scoffed louder than I've ever heard someone scoff at my supposed success.

[Kathy]

I just wanna give the PSA for today. If you are struggling out there and you've dated someone and it just didn't work out, here's what you need to do. Write a book about it. Wait for her or him to reach back out to you. And. And life will be fast.

[Jared]

Well, here.

[Kathy]

And then there's.

[Jared]

Here's the thing, Kathy. I'm sorry to interrupt, but, like, you know, the. The reality is life is messy. You know, like it's not going to work out the way you thought it would. It's not going to be, you know, and I've. I've always, you know, I'm consistent. I've been doing dating podcasts and dating advice for 15, 16 years, as weird as that sounds, Because I've been getting questions and doing podcasts, advice podcast for that long. And the consistent part was always that every situation is its own situation. And you know, if it's raining out, bring an umbrella. Be a better buyer. Like don't, don't just do something because someone else did it. You know, don't not do something because someone else said here are the rules. You don't text this. You know, consider your situation and go forth. And as the situation you know didn't

[Susan]

come with instructions, life doesn't come with instructions.

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[Kathy]

Jared, here's the thing. Back when you had a podcast, yeah, we, Susan and I talk about this as a single man, which you were up until 10 minutes ago when you broke my heart. When you were single, did you and people wrote questions, did you live by the advice you gave?

[Jared]

I always said that it is way easier to be honest on a podcast than it is in real life.

[Kathy]

Oh, my God, you're so right.

[Jared]

Like, you know, advice, easy to give, tough to take. You know, like, that's the fun of a podcast, is we can dis. And, and I think what happens is on podcasts, I, I wouldn't listen to a podcast that wasn't as vulnerable as I was being with the podcast I'm listening to. You know, there's a lot of people selling, you know, snake oil. If you're not going to reveal things about your life, then why would I come to you for advice on mine? I need to judge, you know, where you're coming from and how and your life experiences. You know, I, that was what made dating so hard for me, is that I was so open, you know, with how I dated and how I am. I'd have to answer to myself, you know, if someone was dating me and heard my advice, they go, well, you said, yeah, I'd be like, don't listen to that piece of. He's a chubby loser. He doesn't. He's never committed in his life. And then he'd be like, well, you said on this podcast that, you know, after the, you know, so it's like I had to be held to my own words, you know, if I, like, hid, you know, big facts about myself. We had this, you know, so I, I'M not gonna.

[Susan]

But that helped you. That's, that was your therapy in your

[Jared]

own way a little bit. I, you know that, you know, I, I don't think the people on Reddit would believe that, but, you know, so.

[Kathy]

Hey, Jared, I'm serious. As somebody who was a very chubby girl as.

[Jared]

You look amazing.

[Kathy]

I'm actually.

[Dietz and Watson Advertiser]

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[Kathy]

Off the script here again. How. Because I will tell you, I had no confidence when I in my younger years because I was incredibly overweight. How has it changed your confidence level

[Jared]

that much has changed. You know what's changed? It's the ability to leave the house. It's like, you know, I think when you don't feel good about your body, it is tough to like go on that date, go feel good. You skip things, you skip, you know, hangs. You, you make rationalizations when you don't feel good about your body, when, when you don't feel good in your clothing, you, you go, well, I can't make it tonight. You know, like, I, I think that's a big thing. You know, I think people can relate to that, especially if you're single. Because when you're single to go on a first date, you have to really, like, set aside a lot of reasonable, you know, thoughts like, hey, you're 41. It's never worked out until. What makes you think you're gonna meet someone you like today? You haven't met anyone you like in 41 years. You don't like anybody. You know, you have to set that. You have to be delusional and, you know, nothing feels less, you know, it's tough to delude yourself into thinking the pants fit when they won't button, you know, so.

[Kathy]

Okay. But I gotta say, I gotta say the re. One of the reasons I brought this up was I grew up in a, that we called it the Twiggy culture. Skinny, skinny, skinny. I'm glad to see that now. All sizes, all shapes are welcome. People are much are welcome. I love seeing models of all different sizes, shapes, I think, Kathy, what are

[Jared]

you running for president?

[Kathy]

What is this someone needs?

[Susan]

No, but you get full figured women and they look stunning, sure, but they, I don't. And they're confident now.

[Jared]

You know, like, I, I, I don't, I think there, I, I think there's maybe a space for it and there's a place online for it. But as you guys know, the online world doesn't represent the real world every now and again. You know, that's a, I, I as con, I mean, I'M a comedian who goes on stage and, and, and tells jokes. And people would think I'm the most confident person in the world. I don't care how someone. I don't care how loudly someone screams on the Internet about how confident they are. They're not.

[Susan]

You know, you fake it till you make it, babe.

[Jared]

Right. And, and that doesn't mean the world treats you in the way that you should be treated. Sometimes the world isn't fair to you. And, you know, I, it's just, I, I, I, I'm. I'm happy there are spaces for people, but I don't think that makes it easy for people. When it comes down to you in the mirror and the date that's in a half hour and you're sweating because you just got out of the shower and the pants that you thought you were gonna wear don't fit.

[Susan]

Oh, it's all.

[Jared]

I, I just want to scream and say the world and sorry I can't make it. Good luck with everything. I'm just going to die alone in this coffee.

[Susan]

Because that was your. Your way out was saying, I'm not going to go. That's. You ran from that all that time. And now at 41, you're feeling yourself, baby, and good.

[Jared]

You know, I'm feeling myself. I got to beg people to.

[Kathy]

He's been feeling himself.

[Jared]

I, I feel yourself for years.

[Susan]

He's been feeling himself.

[Jared]

I just did shows in Jacksonville for 15 people. These two people brought Stanley water jugs with alcohol in them. Like I was performing at a campground. You know, I'm still a loser. You know, like, you're not a loser. I performed in a Ramada Steak and Shake last weekend. Okay. Things aren't that great.

[Kathy]

So wait, I have a question. Other. Before Emily, because we're getting out of that.

[Jared]

There's no, there's nothing before Emily. There's only Emily.

[Kathy]

No, no, no, Seriously, I'm good. What was the longest time you ever dated someone? Seriously?

[Jared]

Two and a half years. I was like, you know, but that was young. I was very young. And then, you know, I was. Two and a half years I lived with a, a woman. And then we broke up. And that was like pandemic kind of. You know how pandemic everyone. You went one way or the other. You'd have people that like, run, jump, or they got out that I was the, the opposite. My brother got. Met a girl this day. I moved in with my ex. They ended up moving in when I moved out, you know, like, so. So that was a serious Relationship and then I was single for, you know, 2021 till 2026. So but you know, a series of three months to five months or you know, over the course of that time.

[Susan]

And I have a question is, does she have a career and is she walking away from something?

[Kathy]

She's in wealth management.

[Jared]

She's a, she's doing great. She's got her own, she could work at home. She, so she works at home. She does a lot over zoom and stuff like that, you know, like the way, that's the way of the world. It was. But you know, that discussion of like, you know, move down here figured out, you know, I kind of was like, I can go, I can do whatever if, if it's important you to be, let's figure this out again. It was the negotiation. Let's talk.

[Susan]

Yeah.

[Jared]

You know, there's no wrong answers, you know, I, I, yes. Right. Well, as much as you can with, you know, not to say it won't come up again. You know, listen, I got back from Jacksonville, I said maybe I got to move back to New York. I just did five shows, you know, in an alligator swamp for a bunch of idiots.

[Kathy]

Okay everyone, that's all for part one with Jared. Stay tuned for part two dropping next week. See you then.

[Dietz and Watson Advertiser]

I just received my order from Dietz and Watson. I am so excited. I got chicken sausages and flavored cheddar cheeses. I think my favorite one was the champagne cheddar. Dietz and Watson has been handcrafting premium meats and artisan cheeses for over 85 years. They're family owned and operated and they've never cut corners, ever. Dietz and Watson is simply made. It's as simple as that. Visit Dietz and Watson.com the right way to learn more about the deets difference.

[CeraVe Advertiser / Product Promoter]

If you are looking for a cute new pair of sandals for summer, you have to check out Reef. I have been on the hunt for a perfect pair of flip flops. So I was so excited when I got my pair of reefs because not only are they so cute, but they're actually comfortable and exactly what I've been pinning to my Pinterest board. They have been doing this forever. It's kind of their thing. Flip flops, platforms, slides, premium materials and so stylish. So whatever your vibe is, they have your wardrobe set for everything on the agenda. Styles for the beach, brunch, date night or vacation. They're super comfortable, they look great and you'll feel effortlessly put together. Explore the full collection on reef.com and get 15% off your first purchase. You know that pile of clothes that you've been meaning to deal with? Yeah, same. This is the easiest way to clean out your closet, send your clothes somewhere better and actually get rewarded for it. No more letting things sit around wondering what to do with them. You just fill up a take back bag with clothes that you don't wear anymore, send it in and Trashy takes care of the rest, keeping it out of landfills and giving clothes a second life. It's such a simple way to feel good about clearing space and doing something better for the planet. And here's the best part. You earn cash rewards back for every bag you send, which makes it even easier to stay consistent. You can check it out at Trashy I.O. plus with Trashie Unlimited you can get unlimited bags for just $48 for your first year. An easy at home cleanout system so you can stay on top of things all year long. Clean it out, donate, earn rewards and head to Trashy I.O. to get started. Today, history is full of mysteries like how people ever survived before. Modern laundry detergent Luckily, Tide is here with boosted stain fighting for cleaner, whiter, brighter and fresher laundry versus Tide. Simply no wonder it was America's number one detergent in sales last year. If it's got to be clean, it's got to be Tide. Tide is a proud sponsor of the Elton John Impact Awards, honoring those who have helped shape a more inclusive and compassionate world with their artistry, advocacy and unwavering commitment to equality. You won't want to miss the Elton John Impact Awards podcast, available on June 1st on the iHeartRadio app and everywhere where podcasts are heard. Think about it.

[Podcast Host (Ad Read)]

When it comes to your own food, you can walk into a restaurant, see what's being made, and know exactly what you're getting. But with dog food, most brands keep that completely hidden. Just food for dogs does the opposite. They've built their entire brand around open kitchens. You can actually walk in and watch them prepare your dog's meals with real human grade ingredients like chicken, beef, carrots and peas cooked right there in front of you. No mystery, no behind the scenes, you're not allowed to see. That kind of transparency is rare in the pet food world, and it's a big reason they've become the number one vet Recommended fresh dog food Earning trust from pet parents who want to feel confident in what they're feeding When a brand is willing to show you exactly how your dog's food is made, it says a lot about the care, quality and standards behind every meal. They produce nothing to hide, everything to love. Go to justfoodfordogs.com and get 50% off your first order. This is an iHeart podcast. Guaranteed Human.