In this episode of the Rewind podcast, hosts Steve and Matthew AI explore the nuanced role of vulnerability in dating. They argue that being vulnerable does not mean unloading every insecurity on a first date; instead, it requires strategic timing, discernment, and an awareness of the social context. The conversation distinguishes between authentic self‑expression and oversharing that can derail a fun, relaxed atmosphere. They emphasize the importance of bringing warm, positive energy in the first five minutes, assuming the best intentions of the other person, and treating a date like a guest‑host interaction where both parties are responsible for making the experience enjoyable. Practical examples illustrate how excessive self‑deprecation, venting about exes, or sharing therapist‑level details can be inappropriate, while modest, relatable anecdotes can foster connection. The hosts also discuss how a partner’s reaction to a small “chink in the armor” can reveal their own comfort with vulnerability. Throughout, the tone is conversational and supportive, encouraging listeners to balance authenticity with social awareness to build healthier dating dynamics.
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When people talk about they struggle to be vulnerable, I was trying to think what that means because we don't really mean when you are being vulnerable, you don't mean early on you want to reveal every pertinent fear and phobia and worry and inner insecurity you have to someone. What is it you want to reveal at the beginning or when you're dating someone? Is it just that you think you are putting on a pose? and you want to drop the pose with someone. And I guess for some people, they find it hard to ever drop the pose, and that's why they're always being the witty one, the cutting, sarcastic one, that sort of thing. But do you think it's like people just don't want to lose control?
Yeah, yes, yes, they don't want to lose control. And by the way, that can go in two directions. It can be by never revealing anything about yourself, or you get that person who is self-deprecating in a really brash way where they always voice their insecurities and they always talk about every part of themselves and whatever. And it's like a kind of, in a way, it's its own defense mechanism, isn't it? I'm gonna. I'm gonna tell you everything about me. And if you don't like me for me, then screw you. You know, this is me. And I think that is also a sort of. God, it's a. It's a really aggressive form of vulnerability where you're preempting any way that you could be rejected by them by either rejecting yourself first or wearing it really brashly, like you. Well, if you can't handle me, then that's on you. Like, I'm gonna just be me, and I'm gonna tell you everything about me, and that's up to you. If you can handle it, handle it or not. And it's like, well, you don't. need to say everything all the time. Like, you know, the, like, I speak my mind. I speak my mind. And you know how annoying the person is who says, I speak my mind. Like, well, not every thought you have is something that needs to be said or is useful to the rest of us.
Yeah, that person's never the most charming one in the room or the most interesting one to talk to.
Part of great conversation is knowing is, is being Discerning about what to say and what not to say. It, you know, you may say vulnerability may say to maybe saying to someone, I was a little nervous coming on a date. You know, I haven't been on a date in, in a minute, but it may not be saying I I I. For the last three hours, I kept changing dresses because I felt like I looked overweight in every single one of them. like that's not.
Right? Yeah, that's a good example.
Yeah.
What is that then? That is vulnerability, that second one. But it's a kind of, is it an overexposure?
Is it a bit of an overshare in a way? You know, there are things that are appropriate for a first date isn't therapy. they're not being paid.
Yeah. Yeah. It's supposed to be fun.
It's supposed to. You're supposed to have a good time. And you have to ask yourself, it's like those guys. Remember the guys on the Montreal episode of Anthony Bourdain, Parts Unknown, where the guy who he has dinner with in Montreal says he literally sees being. He sees hosting as an art, but he also sees being a guest at someone else's dinner party as an art. Oh, yeah. And He will come with stories prepared, whether he's the guest or the host at a dinner party, because he believes in the art of being a great guest, of being a great host. And Bourdain kind of laughs because he's like, wait, you prepare stories? And he's like, yes, absolutely I do. Because it's my job to go and be a great person to spend time with. And, you know, you may or may not go that far on a date, but there's something to that. There's something to understanding that part of our responsibility on a day, I'm not saying it's not both people's responsibility, but being yourself doesn't mean not working to be an entertaining person to spend company, to spend time in your company. You can be yourself and try. And being entertaining is not wearing every one of your emotional wounds on your sleeve. That's not funny. Yeah, it's like, like, it's not entertaining.
Going on the date and revealing all these ways you think you're a total mess and what you'd say to your therapist, it's like you've picked the exact wrong context. It's not that, oh, they can't handle me. It's that they're thinking, why, why in this moment when we're supposed to be having fun and getting to know each other, am I getting revealed traumas or revealed, you know, deepest insecurities? It's like it's inappropriate, right? So it is, yeah. It is a timing issue. That's why I think some people do think, so what? I can't really be myself. And it's like, no, there's always a timing and a strategic time to be your weaker self.
Yeah, exactly. And look, we reveal our wounds in all sorts of ways. Sometimes it's not by saying, I have this deep, dark insecurity that I'm not enough. Sometimes it's like, you know, the great one is, like, where someone's, like, telling a story, and. And so it's like, oh, so you went to Antigua. Who did you go with? And they're like, oh, I went with my ex-husband but the less said about him, the better. And you're like, okay, well, they get that. That's a story for another time.
Yeah.
Okay. Like, what? What's someone supposed to do with that? Like, you know, the snarky comment made about someone or gassy comment made about someone or. you know, I remember. I remember years ago being on a date with someone who. Who's, like, just spoke with such Venom still about their ex. And I just remember thinking, why are you telling me this? This isn't. This is not date conversation.
Yeah.
Like, you may have a problem with your ex, but don't. You don't. Like, this isn't the time to bring Venom towards someone else. This is the wrong audience. Like, know your audience. Your job on a date is to bring the best of you. It's not like, take me as I am. Well, is that fair? Like if you took you, if you're having a shitty day, and that means take me as I am means take me as a shitty person today because I'm having a bad time. That's not fair to the other person. Don't go on the date.
Yeah.
Don't go on the date. That's more fair to the other person because they've given up their time and energy to be with you tonight. like, that's not respecting someone else's time and energy is to, is to bring that to them. It's not, I'm just being myself, you know? And I've said this to you before, Steve, I don't just make a video and go, well, you know, if I'm, if I'm feeling really negative today, the audience is going to get that me because that's just, I want to be me. Yeah. Oh, they expect better from me today. They, if I'm gonna get on and make a video, then I have a responsibility to, to bring an energy that is good for people, not an energy that brings everybody else down. I mean, honestly, the things people say where they don't read the room, like, this is what's called for in this moment. It's fascinating to me. And it's how little sometimes people are preoccupied with being charming, how little they are preoccupied with coming across well or just coming across as a nice person, a kind person. You know, how many people don't think it's their job on a first date to show up and give someone really warm energy in the first five minutes? How many people think it's someone else's job to come along and impress them? Well, I'm going to see if I like you first.
What?
Someone came out to see you. You don't have to go on another date with them, but you're there.
Yeah.
You're there. So give them your best energy. And it's the same thing when someone goes on a date and they, it's always like you're immediately assuming bad intentions instead of just going, you know what? I'm gonna assume the best intentions right now. Just for this moment, I'm gonna, you know, hear what someone does for a living. I'm gonna get curious about them. I'm gonna see what they're all about. I'm just gonna listen and be impressed with some things about them. I don't have to act impressed with things I'm not, but I'm just gonna give them the benefit of the doubt as a human being. Because when we do that, people warm to us. They become their best around us. And we may decide at the end of it, I didn't like the vibe I got from that person. I don't want to see them again. We may decide that, but for the time we're with them, unless they do something obviously disrespectful, obviously egregious, assume the best of that person. Assume the best intentions, assume the best traits, because you want to have a nice time and people tend to rise to the occasion around people that actually see them in a positive light.
Yeah. And I think with the vulnerability thing, it's always that thing of, you talk a lot about unique pairings. I think you can, that can get popped in at some point or it will come naturally. There might be a point where you'll say something a little more vulnerable or a little more honest. And, but if that's interspersed with you also being self-confident in other ways, being self-assured being, you know, you know who you are in other ways and you don't think, well, I'm a complete mess. You're like, no, I've got all these things, these things that are great and these things I love about myself. But then it's all in context and it doesn't feel like such a big thing. And you can always decide, right? If they react badly when you show one tiny chink in your armor and they suddenly are like super, like, uninterested or they judge you, then you can be like, okay, that tells me something about this person. You'll find that out.
But you'll know that person who doesn't value vulnerability because they won't be vulnerable themselves.
Right.
You'll literally, you'll see a lack of humanity in that person. You'll see someone who is, you know, everything they do on a date is perfect and they never can laugh at themselves. They take themselves very seriously. They're always talking about all of the impressive things about themselves, but there's never any like that human warmth that, you know, that person who you can relate to. It's the same thing, isn't it? Whether it's a politician or a celebrity or whoever, when we talk about, oh, you know, he's the sort of, he's the sort of politician or the sort of celebrity or the sort of whatever that you'd want to grab a beer with. What we're saying is that's someone who feels like a human being. Yeah, that's someone who feels like I could actually, you know, relate to them. Before you go today, I have something for you. If this year is the year you want to meet your person, it is a free training I did called dating with results that shows you how to avoid the early mistakes that people make in dating. Finally meet your person and get the safety and the commitment that you deserve with them. Go to dating with results to watch this free training right now and don't forget to let me know what you think.
