Grow your dating confidence and ask someone out IRL

Summary

Life Kit: Grow Your Dating Confidence and Ask Someone Out IRL
Host: Marielle Segarra
Release Date: July 14, 2025

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Introduction: The Art of Asking Out in Real Life

In this engaging episode of Life Kit, host Marielle Segarra delves into the nuances of building dating confidence and the strategies to ask someone out in real life (IRL). Drawing from personal anecdotes and expert advice, Marielle explores practical methods to enhance self-assurance in romantic pursuits without relying on digital platforms.

Personal Anecdotes: Dylan Mietanen’s Creative Approaches

Marielle begins by sharing stories about her friend, Dylan Mietanen, who exemplifies confidence in his unique ways of asking someone out:

• At 00:19, Marielle recounts, "I have this friend who's really good at asking people out...he saw a guy outside who he thought was cute."
• Dylan Mietanen elaborates at 00:34, describing a scrappy method: "He opened up a Google Doc on his phone, turned the font size all the way up, typed out his number...it didn’t really go anywhere after that, but it was a scrappy sort of idea."

Another inventive technique Dylan employs is handing out business cards as a low-pressure way to express interest:

• At 01:15, Marielle mentions, "Another way Dylan has asked people out IRL is by handing them a business card as he gets off the subway."
• Dylan explains at 01:25, "If they reject you, you don't face that rejection in person. You just, you lost a business card and that's okay."

Dylan’s methods highlight that confidence can be nurtured and that creative approaches can make the process less daunting.

Building Confidence: Insights from Regina Bonds

To further explore confidence building, Marielle introduces Regina Bonds, a confidence coach, at 02:44. Regina emphasizes the importance of self-awareness and mindfulness in developing confidence:

• Regina Bonds states, "Meditation... allows you to get to know yourself and sit with yourself without judgment" (05:19).
• She explains the significance of self-reflection: "Who am I? Because chances are who you were five years ago is not who you are today" (05:39).

Key Strategies for Building Confidence:

1. Mindfulness Through Meditation
   Regina advocates for incorporating meditation into daily routines to enhance self-awareness and reduce self-judgment. Starting with short periods, such as 30 seconds to a minute, can gradually build the practice (06:28).

2. Body Awareness and Self-Appreciation
   Engaging in body scans helps individuals identify and appreciate different parts of their bodies, fostering self-love and reducing anxiety (07:33).

Applying Confidence in Romantic Contexts

Marielle transitions the conversation to how general confidence translates into romantic interactions:

• Regina Bonds advises, "You have to speak to yourself highly if you want to get out there and be confident" (09:28).
• She encourages positive affirmations: "Tell yourself that you're the type of person that someone would love to be around" (09:28).

Practical Tips:

• Affirmations and Self-Talk: Developing a personal mantra to reinforce self-worth and attractiveness.
• Making Eye Contact and Smiling: Initiating connections with subtle gestures, such as maintaining eye contact and offering genuine smiles (09:28).

Approaching Someone and Handling Rejection

Marielle and Regina discuss techniques to approach someone with romantic interest without feeling intrusive:

• Regina Bonds highlights the importance of reading body language: "If they look back and smile, that's an invitation... but if they look away, maybe leave them be" (12:14).
• For initiating conversation, Regina suggests, "Give someone a compliment... to open the door to an amazing conversation" (10:31).

Handling Rejection:

• Regina emphasizes maintaining self-worth by not tying personal value to others' opinions: "Don't allow what someone else thinks of you be what you think of you" (19:41).

Meeting Through Mutual Activities: Navigating Group Dynamics

The conversation shifts to dating within group settings, such as workplaces or hobby clubs:

• Marielle Segarra raises concerns about potential awkwardness if the romantic interest doesn't reciprocate (13:51).
• Regina Bonds advises caution: "I do not recommend dating someone that you are in close proximity with on a regular basis... weigh all your options and make sure you both are mature enough to handle if it doesn't work out" (14:25).

Guidelines for Mutual Activities:

1. Take Time Before Acting
   Assess the importance of the shared activity and the potential impact on your participation if the relationship doesn't work out.

2. Expressing Interest Gently
   When comfortable, initiate conversations about mutual interests without high stakes, allowing the relationship to develop naturally (16:31).

Maintaining Confidence After Rejection

In scenarios where romantic interest isn't reciprocated, Regina offers strategies to preserve self-confidence:

• Regina Bonds reflects, "I'm so glad it didn't work out. I'm so glad I didn't do that... I'm so much better off" (19:41).

Strategies Include:

• Self-Love and Acceptance: Understanding that rejection is not a reflection of self-worth.
• Growth Mindset: Viewing experiences as opportunities for personal growth and better understanding one's preferences.

Recap of Key Takeaways

Marielle Segarra concludes the episode with a succinct summary of the essential points discussed:

1. Build General Confidence
   Start with self-confidence through meditation and body awareness to enhance dating confidence.

2. Positive Affirmations and Body Language
   Use affirmations and read body language cues to approach potential romantic interests confidently.

3. Cautious Approach in Mutual Settings
   Take time before acting on romantic interests within groups or mutual activities to avoid awkwardness.

4. Slow Down and Enjoy the Journey
   Allow relationships to develop naturally without rushing, maintaining a sense of self throughout the process.

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Notable Quotes:

• Regina Bonds at 05:39: "Who am I? Because chances are who you were five years ago is not who you are today."
• Dylan Mietanen at 01:25: "If they reject you, you don't face that rejection in person. You just, you lost a business card and that's okay."
• Regina Bonds at 19:41: "Don't allow what someone else thinks of you be what you think of you."

Conclusion

This episode of Life Kit provides a comprehensive guide to building and applying confidence in the realm of real-life dating. Through personal stories and expert advice, listeners gain valuable insights into cultivating self-assurance, approaching romantic interests thoughtfully, and maintaining self-worth regardless of outcomes. Whether you're an introvert or someone looking to refine your dating skills, the strategies discussed offer practical tools to enhance your romantic endeavors.

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For More Life Kit Episodes:

• How to Date Without Dating Apps
• How to Stop Overanalyzing Romantic Relationships

Stay Connected:

• Subscribe to the Newsletter: [e-mail]/lifekitnewsletter
• Feedback and Ideas: email [e-mail]

Produced by Margaret Serino.

Transcript

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[Marielle Segarra]

Hey, it's Marielle. I have this friend who's really good at asking people out. We met when we were both working at Marketplace. One time he was sitting at a restaurant facing the street and he saw a guy outside who he thought was cute.

[Dylan Mietanen]

He was speaking on the phone and just like we caught eyes as he walked by and he was kind of slowly like meandering in the corner. So I was like, okay, maybe, maybe there is mutual interest here.

[Marielle Segarra]

So my friend Dylan Mietanen opened up a Google Doc on his phone, turned the font size all the way up, typed out his number.

[Dylan Mietanen]

I held it to the window and then mal text me pointing at the phone. And he did. I don't think if I recall correctly, it didn't really go anywhere after that. But it was a scrappy sort of idea. And I do think that in certain contexts, like fortune favors the bold.

[Marielle Segarra]

Another way Dylan has asked people out IRL is by handing them a business card as he gets off the subway. He started doing this after someone did it to him and he was super impressed.

[Dylan Mietanen]

Right before he got off the subway, he handed me his business card and said, hey, I would love to go out with you sometime. And I thought, wow, this is something that I need to adopt.

[Marielle Segarra]

He says this move is likely to flatter the person. Plus it's low pressure and low stakes for you.

[Dylan Mietanen]

If they reject you, you don't face that rejection in person. You just, you lost a business card and that's okay. You have a hundred more at home now.

[Marielle Segarra]

You might be thinking, where does this man get his confidence? I could never. First off, I will say from where I sit, Dylan is a gorgeous and kind angel with an amazing fashion sense, epic dimples, and the bounciest curls you've ever seen. So I see why he should feel confident, but he does not actually think of himself as that confident. And he's a self described introvert. He says, though asking people out in real life is a skill we can practice, it's a muscle we can build. And the more you do it, the more confident you get. On this episode of Life Kit, we're going to talk about how to ask out or engage with romantic intentions. The people you meet in person, not on dating apps. And because this is a new skill or a rusty skill for many of us. Confidence can play a role here. That's why I'll be talking to Regina Bonds, a confidence coach.

[Regina Bonds]

Especially in this new age world of dating, everybody's behind the computer screen. I still believe in meeting people organically, but so many people are, you know, they have imposter syndrome. They don't know how to put themselves out there.

[Marielle Segarra]

We'll get into how to build our confidence in general, how to apply that confidence to romantic pursuits, how to approach people in real life without it feeling pushy or creepy, and why you might want to create rules for yourself about where you meet people. Because it is cute when you meet at work, but not so cute when you break up.

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[Marielle Segarra]

Okay, Regina, let's start by talking about building confidence in general. One tip you offer is to practice mindfulness through meditation, which I have to say, isn't the first thing that comes to mind for me when I think about building confidence. But you say it allows you to get to know yourself and sit with yourself without judgment.

[Regina Bonds]

Absolutely. We live in a world where people are constantly comparing themselves, they're judging themselves, they don't even spend time with themselves. And so, you know, for me, meditation, I use that as a tool for my clients to just be self aware of. Who am I? Asking yourself that get still, get quiet. Who am I? Because chances are who you were five years ago is not who you are today. And you may be, as it relates to dating or life or building a career, you may be trying to attract something in your life that you no longer even want, but you don't know because you don't know yourself. So meditation is a way to really open the door to say, let me get to know myself and ask myself, who am I? What do I really like? What do I want? You know, the first romance needs to be with you.

[Marielle Segarra]

Is that as simple as just sitting for 10 minutes? Like, do you need to do a guided meditation or do you want to be actively thinking about these things? Or are you just sort of taking ten minutes a day to sit in silence?

[Regina Bonds]

You know, for me, I've been years in the game, so now I can meditate for, you know, 45 minutes to an hour. But in the beginning, it starts with something as simple as, I'm going to set my timer for 30 seconds to a minute. And if you may have to start with something that's guided, the key is not to beat yourself up about how long you did it or if a thought passed or if you couldn't hold a thought. But in the beginning, it's about, I'm creating space for me to spend time with me. And the longer you do that, the more you'll get better at it. It's almost like going to the gym. You know, you. You don't go in the gym expecting to lift all the weights, but you start somewhere.

[Marielle Segarra]

There's something about meditation that I think can allow us to be more embodied as well.

[Regina Bonds]

Yes.

[Marielle Segarra]

Like for me, I've done, you know, body scans or different kinds of meditative states that, where I'm just like touching different parts of my body, like maybe my stomach or my chest or whatever, and I'm. I've gotten to know where I hold my tension Where I hold my anxiety, but also appreciate myself. The same way that like I appreciate my romantic partners.

[Regina Bonds]

Absolutely. I mean, you hit the nail on the head. What you're practicing is not only self awareness, but you are practicing what I call being very in tune with your body. You know, being able to touch certain parts of your body as far as your hands or you know, your heart, your stomach, you know, your legs. And being able to look at those freckles and say, oh my God, you know, I never noticed that one. Or I love the way that curve feels that creates such a momentum when it comes as it relates to confidence and self love and also welcoming others into your space to know that they're accepted for their flaws too.

[Marielle Segarra]

All right, takeaway one. If you want to build confidence in dating, start by building your confidence in general. Meditation can be one way to do that because it allows you to practice sitting with yourself without judgment. You can also practice tuning into your body. What parts you like, what feels good for you, where you hold tension. This self knowledge can help you understand who's right for you and how you want to engage with them. It can also help you come back to yourself and remember your inherent value. If you get rejected in dating, how does that confidence translate into a romantic context?

[Regina Bonds]

As far as romance, I always say, you know, you have to speak to yourself highly if you want to get out there and be confident. The game starts long before you get in the room, long before you have the dating partner. And so the first step for me, and for what I would tell my clients is to get in that mirror and tell yourself that you're the type of person that someone would love to be around, that someone would love to have in their life. Create some type of mantra that works for you. Talk to yourself like you would talk to a best friend. And then don't be afraid to make eye contact with people. So many people are so timid and shy and scared. But if you have a smile on your face, make a cute little eye contact with someone. If they look back, maybe that's the signal that you can invite them over. You can walk over and say something like, man, that's. I haven't seen a smile like that all summer long. Be flirty, you know, be open.

[Marielle Segarra]

Ooh, now I wanna know your favorite pickup lines. Cause that one was really cute. I really like that. And I might use that.

[Regina Bonds]

Yes, that's what I mean. I am not afraid to give some. I think the best thing to do when you're dating or when you're trying to get yourself out there is to give someone a compliment. You know, we live in a world now where people have so many rules. Oh, he must come to me first. She needs to come to me first. Can we just be open and be nice to people? And that can open the door to an amazing conversation that can lead to other places.

[Marielle Segarra]

Takeaway 2 Confidence in the romantic context can start with affirmations. And I know it might feel cheesy, but the only person who's going to be there when you do this is you. Look in the mirror and tell yourself, I'm the kind of person that someone would love to be around. I'm the kind of person that someone would love to date. Tell yourself some of the things that you like about yourself and your body, too. I know you can think of something, even if it feels hard. Look at those incredible eyelashes and that beautiful smile. Speaking of, if you see someone in the wild who you think is cute, don't be afraid to say hi. You can ask them something about themselves. Compliment their outfit or their smile as Regina suggests. Compliments can be lovely and flattering for the recipient, but steer clear of anything overtly sexual and don't start objectifying them like, hey, sexy, what a juicy booty you've got. Even if you're thinking it. Save that for if you have a relationship with somebody. And yes, this can be a fine line. Sometimes you don't want to scare someone or creep them out. And I think that's why a lot of folks don't approach people at all. I asked Regina what advice she has on that front.

[Regina Bonds]

Okay, so the top thing that I would say, to not creep someone out or to not feel like you're creeping someone out is number one, look for the clues. Body language. Don't be afraid to study someone's body language. You know, make eye contact. Make sure that person looks back at you. If they look at you, you look at them again, smile. If they smile back, that's an invitation. That's not creepy. But if you look at them and smile and glance and they look the other way, that may be a signal to, you know, maybe leave me alone, I'm not interested, or I don't want to talk or I'm busy. So take the clues. I would say would be the first step. But I think for you, you have to be confident in yourself enough to know I'm being real about it. I really want to give this person a compliment, and I'm going to say something. You don't wait to get chosen. You get to Decide if you want to speak up for yourself.

[Marielle Segarra]

Let's say you approached them and you are chatting and it feels like it's flowing, and then you've gotta. You gotta go asking for their number or asking for their info. How might one go about that?

[Regina Bonds]

So from my perspective, if the conversation is flowing, you know, and you have to go and that person is still kind of carrying on conversations with you, I would say something as gentle as, you know, I'm really enjoying this. I would love to. To finish this, but I have to go. Would you like to exchange, you know, information, something as simple as that? And don't be afraid if they don't call you. That's okay. Oh, well, onto the next one. Don't get hung up on one person. Be proud of yourself for putting yourself out there.

[Marielle Segarra]

So another way that we can meet people is through some sort of group, whether it's at work or a sports team or a night class. And to me, this feels hard in a different way because you're worried you might make things awkward or that, you know, you won't be able to go back to the group afterwards if things go weirdly. If you have a crush on somebody that you're seeing in one of these situations, do you recommend taking a lot of time to think about it before you try acting on it or doing it sooner rather than later?

[Regina Bonds]

This is my honest opinion. I do not recommend you dating someone that you are in close proximity with on a regular basis. You have to be very careful. I'm not gonna tell you you can't. But I would urge you to take your time and to make sure that that's something that you really want, you know, to partake in before you do. Because if it doesn't work out, you know, what. What type of environment is that gonna put you in? So I would say wait it out. If it seems like something that you're very interested in and that other person is. Just weigh all your options and make sure you both are mature enough to handle if it doesn't work out.

[Marielle Segarra]

Yeah. What about for something that's a more casual space, like a running group that.

[Regina Bonds]

You do sometimes, if it's something gentle like that, you know, you go to the same gym or, you know, you're part of the same networking groups or some type of chess club and you meeting someone there. There's nothing wrong with getting to know someone. But again, think about it. Are you mature enough to handle this? If it doesn't work out, will you still be able to enjoy your life? The things that you've set to bring pleasure into your own world. So it's all about your maturity level in my mind.

[Marielle Segarra]

Takeaway 3. If you meet someone through a mutual activity, especially if it's your job, be very careful and thoughtful before you ask them out. If things don't go well, that could make this other part of your life miserable or at least awkward for a time. If you're in a more casual space like a club, sport, or you go to the same pottery studio, just take your time, please. People meet this way for sure. But ask yourself, how important are this community and this activity to you? If things don't work out, will you keep going with it or will you have to find a new place to do this hobby? If you did decide to like approach someone that you are becoming friends with, let's say you have a running group and you're like, oh yeah, now me and this person, we go for runs. Yeah, we do you have any advice for people on how to express that with without making it too high stakes?

[Regina Bonds]

Right.

[Marielle Segarra]

And making it also possible for the other person to be like, no, I don't see you that way.

[Regina Bonds]

Something that you said earlier, I think is the number one thing in this situation is to play the long game. You know, if you find yourself liking someone in the same group as you and you're starting to take those one off runs together, or you know, you find yourself meeting for coffee or going out to have a drink after, gently say, you know, I'm really enjoying your company. I was wondering, are you enjoying mine? I mean, we see each other all the time, you know, make it playful. And if they're like, you know, I'm feeling the same way, then that's your open door to have a conversation about it. As long as you're not in a rush, I would say don't stress about it, don't overthink it, just be relaxed about it. Don't try to over control things. If you're enjoying their company, they keep showing up, they keep wanting to meet with you after or before or doing the one off things that is them showing interest. People are so easy to read. You know, honestly, if you study human behavior, people let you know if they like you or not.

[Marielle Segarra]

I love that. Yeah. And I, I feel like there can also be a mindfulness component here too. Like you say, just enjoy each other's company. So often we want to rush things to the next place, but it's a pleasure to just spend time with them. Obviously you've been doing it and you've been liking it. And that's kind of a fun stage too. Just being like, oh yes. Sometimes our arms touch like ooh, yes.

[Regina Bonds]

And the beautiful thing about dating is the exploration, the simple things really savoring in every moment of the journey. It's what's going to make you know, if you make it to that next step, even better. But don't rush through that. That's pleasure, that's enjoyment. That is you, you know, having human connection which heals, by the way. And then, you know, you have to ask yourself, especially if you're going to walk in confidence and if you're going to be a confident person before you start rushing into a relationship, am I really even ready? Do I have space in my life to really operate and function in a full fledged relationship? Or should I just enjoy this dating season a little bit longer?

[Marielle Segarra]

Okay, Takeaway four is to slow down. I know that when you have a crush on somebody you can feel a sense of urgency. Like you have to figure out what this thing is and if they like you back but you actually don't. If it's a good fit, it'll still be a good fit in a few months or longer. We can't give you an exact timeline, but just get to know each other, spend time together, enjoy this stage of the connection and see what else unfolds. This can be protective too, because it allows you to maintain your own sense of self rather than rushing into a relationship and attaching to someone else and what they think of you too soon. So big picture, if you do express interest in someone, romantic interest, and they don't feel the same way towards you, how do you kind of maintain your confidence in yourself. How do you maintain your self worth?

[Regina Bonds]

That is such a beautiful question. The way you maintain your self worth is by not allowing what someone else thinks of you be what you think of you. You know, you really have to love yourself enough to know if it didn't work out, that was just not for you. I can think back to so many times where it crushed my heart back then. Now I'm like, I'm so glad it didn't work out. I'm so glad I didn't do that. Like, do you know who I'm dating now? Do you know, you know, what I've experienced, how much I've grown now, what I am attracted to now. I'm so much better off and so I really understanding that what's for you will never miss you.

[Marielle Segarra]

Okay, thank you so much. It was really nice to talk to you.

[Regina Bonds]

You're welcome. Thank you.

[Marielle Segarra]

Okay, time for a recap. Takeaway 1. To build confidence in dating, start by building your confidence in general. You can try meditation, which allows you to practice sitting with yourself without judgment. You can also practice tuning into your body, what parts you like, what feels good and what doesn't. Take away two. If you see someone who you think is cute, pay attention to their body language. If you look at them and they look back at you and smile, that's promising. If they look the other way or seem buried in their book or laptop, you should probably leave them be. If you do say hi, you can ask someone something about themselves. Compliment their outfit or their smile, but steer clear of anything overtly sexual. Takeaway 3 if you meet someone through a mutual activity, take your time before asking them out and make sure that's what you really want. People meet this way for sure, but how important is this community or this activity to you? And if things don't work out, will you be able to keep going with it? And takeaway 4 in general, slow down. When you have a crush on somebody, there can be this sense of urgency, but if it's a good fit now, it'll be a good fit later. Once you know them better, enjoy getting to know the person without all the pressure to figure out if it's a romantic connection. For more Life Kit, check out our other episodes. We've got one on how to date without dating apps and another on how to stop overanalyzing romantic relationships. You can find [e-mail] LifeKit. And if you love Life Kit and want even more, subscribe to our channel [e-mail] lifekitnewsletter. Also, if you have episode ideas or feedback you want to share, email [e-mail] this episode of Life Kit was produced by Margaret Serino. Our visuals editor is Beck Harlan and our digital editor is Malika Garib. Meghan Keane is our senior supervising editor and Beth Donovan is our executive producer. Our production team also includes Andy Tagle, Claire Marie Schneider and Sylvie Douglas. Engineering support comes from Jay Siz. I'm Mariel Segarra. Thanks for listening.

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