Long post, ye be warned.
Mid 20s/M. Dating has always been very hard for me, and I've spent a lot of time trying to figure out why. The story was pretty standard when I was younger. Oblivious to hints, too afraid to act when someone caught my eye, the usual stuff. I sailed past 21 without so much as a first kiss, and that fact bothered me deeply. Romance and connection had always been something I wanted, I just didn't know how to go about it.
Part of the problem might have been that nobody in my life could give me a straight answer on what dating was even about. Was it about marriage? Sex? Finding someone who sets your soul on fire and makes life worth living? I was told all those things, but those were meaningless words to a kid who hadn't experienced any of it.
I also didn't understand girls, to me they were mystical beings of grace and beauty whose affection could only be earned through esoteric means. Seeing other boys find girlfriends looked like magic, and the ease by which it appeared to happen frustrated me. I knew girls were just people, but without sisters, cousins, or close female friends my age to set the record straight, I never learned how to really connect with them.
Things were better by college. I had some female coworkers I'd managed to get along with, I got a little braver, and I was observant rather than oblivious. I made a commitment to go to every party I was invited to, put myself out there, and finally leave my comfort zone. I kept that commitment, and the final tally was 2 parties and 1 horrible fling with a deeply unstable person. Turns out there weren't as many "opportunities" as I had hoped for.
Graduation came and I wasn't in very good spirits. I had technically achieved my goals, kiss a girl, go on dates, not be a virgin, but with the exception of my first kiss I hadn't really enjoyed any of it. The partner had certainly left a lot to be desired, and I figured that was the problem. I just needed to find the right person, then I'd figure this out.
I had a "right person" in mind, an old crush from high school who I'd never really forgotten about. She was pretty much my only female friend, though we were never that close. Mostly spending time around each other in group settings if at all. I wanted to change that, we were living in the same town again for the first time in years and I knew if I didn't make a move now, I'd never get the chance again. So I got serious, and I made a real effort to reconnect with this girl.
For about 6 months we hung out, just the two of us, and it was sublime. First it was lunch, then barhopping, then hiking and eventually a concert night (she invited me and paid for the tickets). I made the choice not to use the word "date" because I didn't want to add any pressure, and we never got physical, but they felt like dates and everyone I've told the story too thinks something was definitely happening. I was over the moon, but it didn't last. She got a job out of state, and right before she moved I initiated The Conversation to see where things stood. She denied anything was happening, didn't elaborate, and in less than a week returned to the occasional online presence I'd known for years. Ouch.
After a while coming to terms with that, I finally got dating apps to semi-work and went on enough dates with strangers that they stopped being scary. Most went nowhere, I kept an open mind but found again and again that I wasn't really interested in any of the people. Part of it I think was the inequality of dating apps for men. The profiles which actually stirred something in me were in demand, and never matched, so I took dates where I could and tried to make the most of it. Years in, it took a second empty fling for me to finally accept that the apps were too fundamentally toxic to lead to anything worthwhile.
So now it's the present, and my biggest problem is meeting someone who isn't taken. That's a slow process for me, and I still suck at small talk so approaching women never works sadly. I think the way forward is to focus on my own life and happiness, get out more doing social hobbies I actually enjoy, and hope serendipity strikes before I'm an old man. This approach hasn't worked yet, but it feels better. Dating is an old wound at this point, and even thinking about it hurts, but there's still time to meet someone nice. I'm optimistic.