Hey all.

To make a long story short as possibly I was homeschooled through high school, and what's more developed crippling anxiety/ADHD after puberty so I never had a chance to explore normal relationships during this period. These issues persisted into early adulthood, when I worked sporadically, but continued living at home and was a semi shut-in. I always had college aspirations but my ADHD was so bad during this period that I was unable to focus on goals and really get anywhere in life, and it took a long time to finally set my life on course.

Flash forward to now, I'm in my late-20s, am finally enrolled in college, am prescribed ADHD and anxiolytic medications and in most ways have made a complete turn around in my life(doing well in school and work etc). I thought spending so much time sequestered when I was younger would have a long-reaching effect stunting my social skills, but not really: I have actually very strong communication skills and people generally like me. I've had people tell me my entire life I was good-looking, I'm too skinny(5'9 and about 130lbs) but have a fairly athletic build/work out a lot, good communication skills, by most metrics highly intelligent, loyal etc but dates/sex/relationships have proved a lot more difficult for me than they have any right to.

I've had some incipient success but nothing really salient. I had my first kiss with some (very drunk) girl, and more substantively, had a first date with a customer I met at my last job, which actually went fairly well, but the writing on the wall is she's not looking for any type of relationship now even though I could tell she liked me. I know a lot of this has to do with my relationship history, but I really don't know where to go about finding women, and the entire methodology feels really unnatural to me. I've gone out to a lot of bars and actually had a lot of luck/engagement with women I was really interested in but every single one of them ghosted me after really promising initial encounters which was highly discouraging. I get that maybe bars aren't where people go to find a long term relationship but where else do you go to find an environment where the social dynamics are conducive to interacting with a large volume of strangers? It's like social life here is established through the dorms, but due to age it seemed more rational to live off campus, so as a result I feel forever out of context.

Also, it seems petty, but in social environments/work etc, I see women flirting with guys who look a lot worse than I do and seemingly have a lot less going for them in other area and I really don't get it. It's like something puts people off on me when it comes to  emotional and sexual signaling, whereas on the occasions where I've actually been able to sit down and have an in-depth conversation with a girl, a lot of them seem really engaged.

There's social circle game but I don't have all that huge of a social circle. I'm just entering sophomore year, so in my first year here I've made maybe 3 people I'd consider to be "friends" and a few more acquaintances, and none of these have proved really helpful. I have to fight against inertia here because I don't really have any desire for a lot of male friends. Mostly because, while being so solitary most of my life hasn't diminished my desire for love/sex, it has made it so I don't really care much about making male acquaintances. If it happens, good, but just instinctively, spending too much time around people who aren't family and who I'm not romantically interested in tends to grate on me.

I also have this huge psychologically preoccupation with age. OK, so I'm 27 but not psychologically 27. In terms of where I am and the experiences I've had so far(which have been extensive but without the traditional rights of passage typically associated with adolescence and young adulthood), and the fact that I'm just starting school, in terms of emotional development, I'm early-20s at most. Since I'm in college, I'm surrounded by a sea of 18-22 year olds, and I can't help but feel out of place, even though emotionally I'm in much the same place that they are. I could just focus on dating women my own age, but I feel a mental barrier of alienation around them as well. It sounds over dramatized but it really is the dysphoria of being an early-20 something trapped inside of a late 20-something's body and I'm not completely sure how to unpack that just yet. One advantage, is I look extremely young. All of the people I've told my actual age to were surprised and some were even speechless or shocked. I'm really tempted to just pass myself off and tell everyone I'm 22 or something, but I constantly vacillate on whether this is a good idea or not.

I haven't had sex yet, which sort of is what it is as an experience, but the specter of sexual inexperience really bothers me as well. Obviously I'm not going to tell her, not only am I a virgin, I've also never had a relationship of any sort before, because that sends up all sorts of red flags, but I'm left wondering how easy it is to fake, if not sexual skill, rudimentary sexual competence. I don't have to be great and the sex doesn't have to be multi-orgasmic, but would she be instantly able to spot my virginity and would that potentially jeopardize a relationship? 

I hesitated writing this for a really long time but I'm not exaggerating when I say that at various stages, this problem, and almost the existential/unresolvable nature of it has made suicide seem like a desirable outcome at times(contrasted with periods of hope and confidence), and that emotional lability really scares me. I'm at a point where I'm willing to venture and try almost anything, so hopefully some of the suggestions here can help me, and I feel like being able to look at the situation outside of my own head(which hopefully isn't as bad as it seems to me), will be useful.