To start off, I'm 17 and just finishing my last year of high school before college. I'm not much of a social person; I have only one real friend and several many acquaintences. I never took an active interest in having a lot of friends, mostly because there aren't many of my peers at an intellectual level high enough for me to converse with. :S As such, I've never had a girlfriend and have only been on 2 dates before. My experience with girls has always been long periods of nothing where I have crushes but don't act on them, follwed by a break-down where I get so lonely I ask out someone I'm physically attracted to. Then I get ashamed of myself and never follow it up.
There is this one girl who was always better than average. I'm able to talk to her without holding myself back. She's very pleseant and has no real flaws (except one, I'll get to that), yet I've never been very attracted to her. Eventually, around Christmas this year I told myself I had no reason not to like her, and it must be the result of some crippling emotional problems from my childhood. I also knew she liked me in the past. So I asked her out, pulled out the stops, fancy words, flowers, etc. She agreed and we set a date.
What ended up happening was about 2 weeks and 4 postponements later we still hadn't gone out. We also didn't spend any time together seeing as we both had this understanding that it would mean more if we weren't open about it.
We were talking one night and I happened to bring up the one thing I tried to ignore about her: despite being a great person, practically every weekend she goes out with her stupid friends and gets plastered. I've witnessed it before and it's one of the saddest things I've ever seen. Now I don't have a problem with drinking itself, but what scared me was her reason for drinking: I couldn't see one. And when I asked what the reason was she refused to tell me. Then - and I credit this to her being special at least - she knew that we had to call it all off.
Now my dilemma: It's been 3-4 months since then and I'm having second thoughts. Was something like that so important as to not see her? At the time I weighed my values and decided it would be too painful being with her and knowing she's killing herself for some hidden reason. Now I'm wondering if the joy of being with her would've out-weighed it. There's almost no chance she'd try it again, she hasn't changed; if anything, she's gotten worse. But I can't rest now that I don't know if it was a mistake or not.
Secondly, though I know a relationship at my age cannot really go anywhere, I'm scared that when I do find a girl I love later in my life I'd be too inexperienced to get her. As it is, I only just had my first kiss in October; it was also my last. :S
I'd really appreciate it if somebody helped me with this. I can't think of anybody more suited to give me advice than fellow Objectivists.
[Moderator's note: This led to some discussion on alcohol, which can be found here.]