Where should I restart?

I’m a 21-year-old man who’s had little experience in dating. I’m making this post because I want to have more experiences, but find it difficult to get myself into them. I’m interested in hearing what advice this community may bring! Thanks for reading.

I grew up heavily isolated (online) and was homeschooled too. My staggered social skills and ADD have put me socially “behind” most people in many ways, but ahead in other ways such as by developing communication skills most don’t have the time to develop (I did this by managing projects online in teenage years).

When I was 19 I met and eventually flew out a 31-year-old woman that I thought I was in love with. She quickly became pretty scary and imposing and almost right away I felt like I’d made a mistake but I deal with stress by emotionally shutting down and becoming very analytical. She took my virginity and she stayed for about 8 days.

I broke up with her a few weeks after she flew back because beyond the age gap, there were many red flags and things I was uncomfortable about. She was devastated and could not deal with it, causing so many boundary breaks within mutual online communities that nearly a year later I completely blocked her.

I did date a guy my age a couple months later since I wanted to see if I was bisexual — I’m a curious person and like to try new things) but it didn’t go that great since he was more interested in a hookup. We did things like making out, but after I didn’t want to do anything past that right away (oral), he stopped showing interest and we stopped seeing each other.

That takes us to now. I’m a junior in college and don’t really know where to start. I work a lot (being a youtube content creator) and so I have a pretty different lifestyle and work life than most people. But I want to date, I just haven’t figured out how.

I’m attracted to older women but that experience was traumatizing and I never want that again. And when it comes to men, I’m just not really attracted to them sexually. Women my own age, I’ve noticed are really hard for me to approach. My great communication skills are useful for work and management but mean very little in flirting or showing romantic interest. Being a good communicator does not mean you are charismatic — there is a distinct difference.

I commonly don’t get subtle hints, and am always worried about over stepping boundaries (i try not to stick around people for too long or overstay my welcome) I think this fact prevents me from getting into organic situations where I’d strike up a conversation. I’m definitely getting better at conversing but I feel isolated and “different.”

Getting the ADD diagnosis and medication prescribed helped me a lot but it doesnt stop me from knowing my brain chemistry is different. While I’m okay with the feeling that I never fit in now, that feeling is still there.

So with that said, does anyone have advice for how I should approach dating? I want the closeness of having someone to hang out with, have a romantic and sexual relationship with, and get to know, but what do you recommend for me to find that?

Thanks!
N