I was talking to a friend last night, and he pointed out that I tend to put a lot of pressure on myself when it comes to dating. He suggested I try to relax and just have fun with it. He’s not wrong, I do have a tendency to overthink things but on dates, I really do my best to be laid back and fun.

You see, I’m 27 turning 28 in a month, and I’ve never been in a serious relationship. The closest I’ve come was a situationship that lasted about a month when I was 24, which also happened to be when I lost my virginity. So yeah, I guess you could say I’m a bit of a late bloomer. 

Even though I’ve never been in a relationship, I’ve never let that hold me back from living my life or doing the things I want to do. That said, I’d really like to experience being in one. It just seems nice to have someone who genuinely likes me in that way. It’s tough though, watching my friends, many of whom were single not long ago get into relationships, get engaged, or even get married. I’m happy for them, truly, but it also makes me question what I might be doing wrong.

I’ve worked really hard on myself over the years. I’m much more confident now, and I’ve learned to hate myself a little less. Honestly, the person I was five years ago wouldn’t even recognize who I am today. Still, it doesn’t always feel like enough. I know I’m supposed to tell myself that I am enough, but it’s hard to believe when life seems to keep proving otherwise.

It feels like there’s always someone better someone more attractive, more confident, and more desirable. Why would anyone settle for me when there are other guys with similar personalities but better looks? My hair has also started thinning. It’s not too noticeable yet, and I’m doing what I can to slow it down, but I know it’ll be gone in a few years. On top of that, I can’t grow a proper beard best i can grow are some gross face pubes that I shave off weekly.

I worry that as I get older, it’ll be harder to meet someone. I imagine most women in their 30s wouldn’t be thrilled about dating a guy with no real relationship experience. And as a Dominican, there’s also the added pressure from family. Ever since I graduated college, I’ve been asked, “So, when are you going to settle down?”

Last year was actually the best year I’ve ever had in terms of dating. I went out with 13 different women, but none of those dates led to anything serious. It’s frustrating because I have friends who didn’t need to go through so many people to find their partner.

At this point, I don’t really know what else to do. I have a great group of friends, and I genuinely enjoy spending time with them, but I can’t help feeling like something’s missing. And that “something” feels like being in a relationship.