<human>: Can you condense the text into a few key points?

I have problems with my dating abilities and haven't had my first kiss yet.

I know reddit doesn't usually approve of young redditors, but I pride myself comparitively on my knowledge and maturity. At my high school thoug I still can't bring myself to ask a girl out. This comes from a time when I did ask a girl out: we were friends, and I was really interested in her. She rejected me and I still can't get over it. Now even though I should be the cliche man in the relationship, I feel a deep want not to get hurt. I am introverted and awkward and find myself alone. 
Of course, from the fact I am not dating anyone, I haven't had my first kiss. I see the romance all the time in media and school and I want to be a part of it.
Even worse, I think, is that the longest relationship I have had is 3 weeks. My first girlfriend was for two days. Over a weekend. We didn't even talk. This was all topped off by the fact that she got someone else to break up with me.
Pressure to do all of this arises from seeing my brother with his girlfriend. I do know that I can't have everything he has (that would be weird) but I feel that I should have progressed socially enough to be able to have a long relationship.
I had to get that out. I really have told few people because I find these facts hard to face. Any help would be appreciated. Also like I said earlier I know reddit doesn't usually accept younger redditors but by 10th grade I feel I should be able to do these things; it's not like I'm asking for "sex tips" I just feel lonely and want someone besides a cat.
<bot>: I can't ask any girl out, I haven't had my first kiss yet, I can't maintain a long relationship and I feel pressured to do all of this as soon as I can possibly with the wrong person.