secretly_a_potato

So, I haven't had an easy life, constant issues with money, unstable mom, nobody really cared about me or listened to me so I learned to shut up. Got bullied in school daily by teachers and students, didn't really have any friends, just people I hung out with because I'd rather not be alone as it's easier to be bullied when you're alone. I'm not trying to get pity or anything, just feel like that added a lot to who I am now. I'm pretty shy and very quiet, I get more outgoing after I've gotten to know people better, but I only get to know people that pretty much force me to be with them, if I can avoid being around them I will, I'm not sure why. I have some friends that often ask to hang out, I generally go(this is new though, I used to not go, and eventually they stopped asking) but I never ask anyone to hang out with me, I guess it's fear of rejection. Anyway, I feel that what I really need is a more intimate relationship, a friend of mine that I've lately been giving relationship advice(apparently I'm good at it) tried to "hook" me up with a friend of his behind my back, I didn't know he was behind it but I found it strange that she started chatting with me via fb(we see eachother weekly but don't really talk, probably my fault) anyway, she's a great girl, but I don't know if it's just my general apathy towards everything or if I just don't see it going anywhere, he tells me to go for it, but I'm not so sure. I don't know if I'm just scared of being rejected or I legitimately don't feel anything happening, even when I think I feel something I end up making excuses in my head to not go for it("she's too pretty for me", "she's too smart", "she's too dumb", "she smokes", "she doesn't use proper grammar") petty, stupid excuses. The last and only time I asked a girl out was when I was 17, nearly 4 years ago, she said yes, but it was pretty hard to keep the conversation going during the "date", I just don't know what people are supposed to talk about. So, she started convos on fb a few times, we talked for like 2-3 hours, mostly just silly things, nothing too serious or anything, but she stopped doing it, probably to see if I'd start one, I want to, but I don't know what to say or do. I always talk to her in person, even hough it's not a lengthy chat, but I just assume no one is interested in what I have to say. Well, damn, I just rambled a lot and didn't say anything... hope you guys can give some advice, I kinda of know what I need to do, I just need to hear it from others. Thanks.