Dating : In Need of Advice As Every Option I’ve Tried Hasn’t Worked Out
Throwaway because reasons, but this is kind of a crosspost from r/offmychest.
I’m an almost 30 Latino male, I’d consider myself to have a few extra pounds, even chubby.
Most of my life due to family issues (feel free to read my other post) I’ve spent a lot of time alone. Also, around the time I was 23, the main group of friends I had (3 other guys) since high school, phased me out. I’ve made new friends since, but nothing super close, mostly each friend is f I am sure that this has affected me up until now, especially when it comes to dating.
Lately though, and by lately I’d say the past few years, the sense of isolation and loneliness has only kept increasing. I’ve spent a lot of time on my own after my friend group dropped me, learning to be with myself, do things on my own, become self aware and hopefully figure out what happened. I went to (and to this day still) bars on my own, movies on my own, concerts, festivals, trips, restaurants, beaches, etc all by myself and with myself. However, it reaches a point where you’ve separated yourself so much that when you want to reenter the social world, it’s not as open as you’d like, especially as a male over 25. No one really is looking for friends like that, much less do women really seem open to the guy at the bar/club by himself.
I’ve tried dating apps and over the course of 4 or so years I gave up on them as I have never gotten a single match, and I’m not someone with a defined type, I just like who I like when I see them. I think I’m fairly interesting and into a lot of different things, and I’m great at conversation and approaching people, I’m also pretty funny. I may not be the most attractive or fit guy, but I wouldn’t say I’m even close to bottom of the barrel. I have a great and varied taste in music, I collect a few things like sneakers and records, but I’m financially responsible. I’m also very open minded and accepting. My love life hasn’t been stellar after high school. Things have sort of started here and there, but they never turn into anything. I have only had sex once and that was only a couple of years ago (my high school girlfriends weren’t ready when I was, but I respected that). Interestingly enough, just about every woman that I’ve been moderately involved with has ended up leaving me hanging and gone on to be with someone else, gotten back with an ex, or have gotten married and/or pregnant soon after. It’s some Good Luck Chuck type shit without the sex aspect.
Also, in the back of my mind I worry that I’ll fall head over heels for the first woman that shows interest even if she isn’t who is best for me. At the same time, I’m sure most women don’t like the idea of a guy that doesn’t really have any friends. I’ve seen and heard situations where they get offput by the first inkling of clinglyness, and I’m not clingy, but without anyone else to spend my time with they’ll probably end up not liking that I just wait around and do my own thing until we hang out again. Who knows. I know what I like and what I don’t like, and I am open minded enough to know that I will have to compromise on certain things.
Whether it would be a hook-up, fwb, or full on dating, I am open to all of these scenarios. Also, doing all these things on my own isn’t really an issue as I don’t have a problem approaching people, but a wingman would definitely be an asset in these situations. I’m good at flirting, whether in person or through text/DMs, so it’s not like I make it weird. I’m hygienic so I don’t smell and I brush my teeth regularly and have plenty of clothes where that’s not an issue either (although, I do lean more casual). I am open-minded, and never hassle women after it’s clear that there’s no interest. I’m great at conversation and equally great at just listening when it comes to it.
I have plenty of hobbies and interests, none of which are anything out there. I like clothes, sneakers, music, anime, movies, TV shows, sports events (rather go to games than watch it on TV). I’m never SUPER open at first in terms of laying all the cards on the table, but I’m never one to lie via omission. I also have asked friends, both male and female, about the photos on my social media and dating profiles, and I think I have a good mix. My friends also don’t understand how I’ve found myself in this position as I’m funny, caring, not an asshole, but also not a pushover or someone to pretend I’m something I’m not for the sake of possible sex or a relationship. That’s not to say I’m not compromising, I just am not gonna say I like X just because she likes X to increase my chances.
Effectively I’ve been single since high school if I don’t count the false starts. So, I repost this because I’m not sure what else I could possibly add to my repertoire to increase success.
Hi! I skimmed your post a bit.
I think a first step would to be expanding your social circle. I live in a big city so it’s always a bit of a dud when I start dating someone who’s just moved here. Just because he’s going to be clingy; there’s no one else he’s hanging out with. Expanding your circle can also lead you to potential dates. Your current friends like you, your new friends may like you even more to the point where they want to match make for you
Next is appearance. Our friends and family love us unconditionally so they don’t always see us objectively. We also don’t really have a great idea about what we look like all the time. I’d say to get some outside opinions from people you find attractive, if you can swing it. I’d avoid posting on Reddit because people can be mean but you can get some solid advice about more flattering haircuts and clothing choices. It’s also more of an investment but spending time on your health may help as well. Hitting the gym, spending time on facial care, getting your nails done; it all helps.
If OLD doesn’t work with apps I’d say to try a more traditional route like Match or EHarmony. I’d say to find social dating events around you. Speed dating, matchmaking happy hours, or similar events may be lucky.