Life Kit - Grow your dating confidence and ask someone out IRL

Episode Date: July 14, 2025

In the era of online dating, asking someone out in real life has become a lost art. This episode, confidence coach Regina Bonds shares tips on putting yourself out there, bouncing back from rejections and talking to people in person.Learn more about sponsor message choices: podcastchoices.com/adchoicesNPR Privacy Policy

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You're listening to LifeKit from NPR. 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. 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

So my friend Dylan me at an in opened up a Google Doc on his phone turned the font size all the way up Typed out his number. I held it to the window and then Mal's like 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. 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. 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. He says this move is likely to flatter the person. Plus, it's low pressure and low stakes for you. If they reject you, you don't face that rejection in person.

You just lost a business card, and that's OK. You have 100 more at home. Now, 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 gonna 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. 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 know, they have imposter syndrome, they don't know how to put themselves out there. 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. You have your job, but you also have a life and you're not just one thing. Neither is the Here and Now Anytime podcast. Every weekday we break down the biggest story of the day and something else, like a new trend everyone's talking about. It's Here and Now Anytime, a daily podcast from NPR and WBUR.

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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. 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, you know, five years ago, it's 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. 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 10 minutes a day to sit in silence?

You know, for me, I've been years in the game, so now I can meditate for 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. And it's almost like going to the gym. You don't go in the gym expecting to lift all the weights, but you start somewhere. There's something about meditation that I think can allow us to be more embodied as well. Like for me, I've done, you know, body scans or different kinds of, 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'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. 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.

Being able to touch certain parts of your body as far as your hands or your heart, your stomach, your legs, and being able to look at those freckles and say oh my god You know, I never noticed that one. All right. I love the way that curve feels that creates such a momentum when it comes when 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 welcoming others into your space to know that they're accepted for their flaws too. 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? 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 to them and say something like,

man, I haven't seen a smile like that all summer long. Be flirty, be open. Ooh, now I wanna know your favorite pickup lines, because that one was really cute. I really like that and I might use that. 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.

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. Takeaway two. Confidence in the romantic context can start with affirmations. And I know it might feel cheesy, but the only person who's gonna 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. 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 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. 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 it 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. Let's say you approached them and you are chatting and it feels like it's flowing and then you've got to go. Asking for their number or asking for their info, how might one go about that?

So from my perspective, if the conversation is flowing 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 on to the next one. Don't get hung up on one person. Be proud of yourself for putting yourself out there. So another way that we can meet people is through some sort of group, whether it's at

work or a sports team or 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 or doing it sooner rather than later? 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 going to 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 type of environment is that going to put you in? So I would say, wait it out. And 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. Yeah.

What about for something that's a more casual space, like a running group that 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 up to bring pleasure into your own world? So it's all about your maturity level in my mind. Takeaway three. 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 were 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. Do you have

any advice for people on how to express that without making it too high stakes, right? And making it also possible for the other person to be like, no, I don't see you that way. 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 find yourself meeting for coffee or going out to have a drink after, gently say, I'm really enjoying your company. I was wondering, are you enjoying mine? We see each other all the time.

Make it playful. And if they're like, 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, 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. I love that. Yeah. And 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, because 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. And the beautiful thing about dating is the exploration, the, yes, sometimes our arms touch, like, ooh. Yes, 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, 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 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? 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? 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 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 think really understanding that what's for you will never miss you. Mm-hmm.

Okay. Thank you so much. It was really nice to talk miss you. Mm-hmm. Okay. Thank you so much. It was really nice to talk to you. You're welcome. Thank you. Okay, time for a recap. Takeaway one, 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. Takeaway 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 four, 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 LifeKit, check out our other episodes. We've got one on how to date without dating apps, and another on how to stop over-analyzing romantic relationships. You can find those at npr.org slash life kit. And if you love life kit and

want even more, subscribe to our newsletter at npr.org slash life kit newsletter. Also, if you have episode ideas or feedback you want to share, email us at life kit at npr.org. This episode of life kit was produced by Margaret Serino. Our visuals editor is Beck Harlan and our digital editor is Malika Garib. Megan Kane is our senior supervising editor and Beth Donovan is our executive producer. Our production team also includes Andy Tagel, Claire Marie Schneider and Sylvie Douglas. Engineering support comes from J-SYS. I'm Mariel Cigarra. Thanks for listening. These days, there's so much news, it can be hard to keep up with what it all means for you, your family, and your community. The Consider This podcast from NPR features

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