From a recent episode of Man Up: Liam is a virgin. Now, I want to make this clear: There is no shame in that. But now that he’s 23 years old and most of his friends have passed that milestone years ago, he’s starting to feel like he’s been left behind. And the older he gets, the worse off he feels. So Liam—that’s not his real name, by the way—has decided he’s on the market, looking for love. But in the back of his mind looms this very difficult question: Is there something wrong with me? He’s decided he can’t afford to wait any longer to find out. Our conversation has been edited and condensed for clarity.

Aymann Ismail: What kind of girls are you interested in?

Liam: I’m into girls that I can relate to. So I’m into fitness and cars. Definitely someone who can—a gym buddy. A workout partner, rather. Someone who I can have a somewhat intelligent conversation with, and someone who just wants to be around me. Someone who wants to be intimate. Someone who wants to hug me, at least. I just think about that all the time. Just hugging someone. It just hurts so bad. [laughs] It’s like, “Somebody want me, please.”

To hear him describe his virginity, it’s like he’s longing for some type of intimate connection. He’s sure he should have lost it by now and even blames himself for not sealing the deal when he had the chance.

Oh, my God. I had the clearest opportunity to lose it when I was 18, and I beat myself up for it every day. Oh, my God.

What happened?

OK. I was 18. I literally had the house to myself with my girlfriend at the time, and she literally came over by herself. Her mom dropped her off. And my parents were gone until like 9 o’clock that night. And basically she came over and I just suggested, “Hey, let’s play board games on the floor in my room.” Or “Oh, let’s draw some pictures. Let’s watch TV, play video games, take a walk in the park.” So we were over there for like six hours, and all I did was suggest platonic activities. Now looking back, I wish I made a move or tried something. And it wouldn’t have been mean. Because I kept having this fear that it would be disrespectful or mean for me to make a sexual advancement towards a woman. But she’s probably wondering why I hadn’t done it. So looking back, yeah, I was just kind of too nice. That was an obvious chance for me to lose my virginity, but I didn’t. And she was nice, but I was a little bit too nice to her, if you get what I mean.

You keep saying that you were too nice, but was it coming from a place of politeness? Where was that motivation of wanting to do platonic things coming from?

It was coming from the fear of messing things up. I just felt like if I maintain this attitude, if I just had a consistent personality with her, then she would stick around. It was my first girlfriend. I didn’t want to lose her or anything. I didn’t want to do anything to mess it up. But also, I’m not going to lie, a part of the reason why I was being so nice is because I actually thought that girls are kind of sick of dealing with guys who are mean to them or are assholes to them. So I figured if I was nice, that would increase my chances of having a successful relationship. But that’s kind of the opposite of how that works, I quickly learned.

What do you mean by that?

Like they don’t necessarily want someone who’s going to be kissing their ass like that. They want someone who’s—there’s a difference between being nice and being a pushover, and I think I was being a little bit of a pushover.

The way you’re using “nice” has me so paranoid. I’m like: “Yo, please don’t turn into an asshole. Please don’t turn into an asshole.” Because, I mean, just to be real with you, man, I don’t think being nice is—I’m not sure that’s the issue. I really liked what you were saying earlier about how there’s this fear inside you that doesn’t want to fuck up. And so I’m really afraid that if you’re looking up how not to be nice, that you’re—

Oh, I’m not doing that.

—going to find something that’s like, “Yo, give her a compliment sandwich between two insults,” or that type of stuff. I’ve seen some of these relationship coaches, and a lot of them are great, but some of them are just toxic.

Yeah, exactly. I’ve seen those, and I typically stop watching after a few minutes. But yeah, that’s just me. I’ll never be—I’d be terrible at trying to be not nice.

What do you think you’re going to get out of losing your virginity?

It’s just painful knowing that I’m not doing that, or not sexually active. I want to be so badly at this age. And I just feel like I’m getting older and older and things are going to get more awkward and more awkward. And it’s such a simple thing. People have been doing it ever since the beginning of time. It’s just like, why is it so difficult for me to experience that?

Also, I know I’m a grown man, but I feel like doing it will make me more of a man. Because I honestly feel a little bit like a child when it comes to dating and confidence in general. I’m kind of an introverted guy. I can talk to strangers, but I feel like it would just help me in the confidence department a little bit once it happens. You know what I mean?

Yeah. I’m wondering, why do you think it hasn’t happened?

Well, I kind of went on this two-and-a-half- to three-year period where I was literally OK with just doing my own thing, going my own way. But then after about three years, I just kind of cracked. I’m just like, Ah, I can’t do this. I’m too young. I want a girlfriend. So I went back into the seeking-a-relationship type of mindset. And what I’ve been doing with that is just experimenting with all the dating apps. I’ve literally tried them all. I’ve literally paid for all of them, like the premiums, so I get more matches and stuff. And I just haven’t been successful. You’re familiar with the term ghosting, I’m assuming?

Yeah. It can be really rough on online dating. I mean, I did it for a little bit, and I definitely felt like the other gender had the pick of the litter.

Yes, exactly.

Do you have a go-to strategy? What do you usually start a conversation with?

That’s where I struggle.

Let’s talk about it, man. What do you do?

Well, when I first started out, I would just be like, “Hello.” And I quickly figured out that didn’t work. So I Googled, looked at some articles on what the best thing would be to do. And they were saying, or people online were saying, pick out something in their picture and compliment them on it. So then I’d be like, “I like that shirt,” “I like that band,” if it’s something I can relate to, or just point something out. And then I also heard you should try to make some jokes or be funny, but that just didn’t feel genuine coming from me. I’m not the kind of funny guy. I’ve tried all sorts of things.

So what are some other challenges that you’ve been experiencing so far?

Honestly, just being interesting in general. I feel like I don’t have—

Just being interesting?

Yeah. Like an interesting, extreme, daring lifestyle that a girl would want to be a part of. Because I’ve watched some videos on YouTube, and basically, it’s like, women want to be in your social circle. If you have a cool life, they want to tag along and be a part of your cool life, you know? And I just feel like I don’t really have that. I just think, why would anyone want to be with me? I just have a basic, boring life.

Liam’s talking about losing his virginity, but what I’m really hearing him say is he just wants to find someone. All of his concerns with being too nice or not being interesting enough—I had all those ideas too. What helped a lot was getting to understand it all from a woman’s perspective. And I knew just whose to get.

To hear the entire episode—including advice from Andrea Silenzi, host of the hit dating podcast Why Oh Why, and what happened next for Liam—subscribe to Man Up on Apple Podcasts, Stitcher, Spotify, or wherever you get your podcasts. Look for the episode “A Virgin in His Mid-20s Starts to Worry.”