I grew up in a rather toxic environment and therefore, didn’t have much self-confidence as a kid. It took me years and finally going to therapy so that I could work on myself to become a version of myself that I feel would… I don’t know. Be a good partner? Not repeat toxic behaviors I saw from my family?

What I’m trying to say is I had a lot of crap that I needed to work out before getting into the dating game. And at this point, by no means am I perfect, but I’ve gone to therapy and I’ve done a lot of self-work to the point I feel like now would be as good a time as any for me to begin dating in a healthy way. But even still, I’m facing a few barriers:

* I’m not attracted to anyone anymore. Even when I see someone who’s my type, when I actually walk through the motions in my head and picture us dating or in a relationship, I realize the idea doesn’t excite me and I abandon it because I don’t wanna be superficial and lead anyone on if I’m not really into them.
* I feel like I’ve been single for so long I would have absolutely no idea what to do in a relationship or how to behave
* I also have conflicting goals… I’m 27 and I want to find “my person” but at the same time, I’ve never had the chance to fool around like a lot of people did growing up, and as bad and superficial as it sounds, part of me is afraid of getting into a serious relationship, eventually losing interest in them, and hurting the person as a result because I never got the chance to “play the field” to see what type of partner I like.
* Where would I even meet anyone? I suck at dating apps and I spent so much time by myself working ON myself that I feel like I’ve almost forgotten how to “people” when it comes to dating.
* How would I even explain why I haven’t been dating up till now? Wouldn’t most women prefer someone with more experience at this age?

tl;dr: I’m entering the dating game for the first time as a 27 year old guy, and I feel like it’s too late for me.

5 comments
  1. I cant comment on some of your concerns but i can say, my dad was a drug addict, my mother has BPD and was abusive and eventually left. I saw her a handful of times in over a decade. Various sets of step parents. Both of my parents have been homeless when i was a child. I lived with my grandparents on and off.
    I didnt meet my husband till i was a few months shy of turning 28. We have 3 kids, a very healthy and open communication marriage. Own a home.

    Just because you experience toxic cycle doesnt mean you have to continue it. I didnt.

  2. I don’t think it’s too late for you, but you can’t date without communicating interest. You can’t communicate interest you don’t have. It seems like this is the issue to tackle first. You might have an avoidant attachment style (fearful avoidant or dismissive avoidant). If you read up on these and figure out which one you are, there are communities here on Reddit that can help you with coping strategies.

  3. My partner was 31 when we started dating. I’m his first serious relationship and the first person he had sex with. I didn’t date from ages 20-30. Had lots of one night stands. I gleaned nothing from it and have a much more meaningful sex life with my partner. The likelihood of your meeting The One out the gate is unlikely, so you’ll have the chance to casually date and play the field. It’s never too late to do the things you want unless you let it continue getting in your own way.

  4. Nobody’s really perfect. It’s very easy for people to seem like they have their shit in place from the outside, but everyone has some kind of trauma, prejudice, damage or other crap going on inside. Don’t worry too much about yours – you’ll fit right in.

    It’s normal not to be able to picture yourself dating a complete stranger based entirely on how they look, or a few cursory interactions. You literally don’t know them. How can you know if you’d want to spend time with someone without knowing what that time spent would be like?

    Everyone starts off single. You’re acting like you’re ancient – 27 really isn’t that old. I won’t say romantic experience counts for nothing, but it’s far from a death knell. You can talk to people. You have basic empathy. You can interact. That’s really all you need.

    I wouldn’t worry about why you haven’t dated so long. Most people are not going to care, if they even ask. Dating isn’t like applying for a job, you don’t need to present your relationship history for examination. If you do start seeing someone, they may ask, and then you just be honest – you just didn’t find anyone you clicked with. You don’t need to get into the why.

    It’s sad to say, but dating apps are sort of ubiquitous. People who want to find romantic connections tend to go to the place specifically designed for romantic connections.

    I’d suggest giving it a try. Stay away from “fast” dating apps like Tinder for now, stick to “slower” ones like Bumble. There is no harm at all in giving it a try.

    If it doesn’t work out, the general advice is to cultivate some social hobbies. Ungendered sports, arts and crafts, board game club, communal gardening, whatever you enjoy. Just, meet people, generally, outside of work. Most people you won’t particularly click with. Some will become friends. Some will become more.

    As far as playing the field Vs dating for marriage… That’s something that has a less clear answer. There is nothing stopping you from pursuing relationships on a casual basis, then dropping them when it feels like they aren’t going anywhere, but I’d say be a little cautious. Hurt feelings are easiest to find in botched casual relationships. You need to communicate clearly without being condescending or rude, and that’s not always easy.

    I’d say don’t worry about it too much for now. Go on dates, without stressing about “where in this going”. Go on dates just with the goal of enjoying the company of your date and doing what feels correct. Some of the dates are going to suck. But that’s normal for everyone – most dates suck, regardless of who you are. Don’t let it dissuade you.

    Best of luck.

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