Am I accepting defeat too quickly?

Ok so there is this guy that I like but I can never pinpoint if it is going well, I have been single 2 years after a 3 year relationship and not been on a single date or been asked out once. It has just been failure after failure with guys. I like this guy who at first was interested we met at a society social and afterwards he spoke to me on facebook chat and at a party I overheard his friend ask him if he fancied anyone and he pointed at me (he thought i couldn't see but there was no one else anywhere near me) since then we have been having the odd chat on facebook chat but I find it hard to speak in person I just freeze up. Also it is normally me starting the convos, he has a few times but a couple of those times he was drunk. When drunk he keeps asking if i find him annoying. He also asked me to come watch him in a performance, I went along but I never spoke to him afterwards cos my friends left and he was busy talking to others. He mentioned that also when drunk. At a party this week we sat on the sofa together and just kinda talked, i wish I had flirted more but there was no real conversation. I spoke to him last night on facebook but he went offline. I feel like giving up, i really like him but I don't wanna get too deep and find he does not like me. He seems to have a big ego to me but his best friend who has known him years says he is really shy and insecure. Should I not talk to him for a while or should I keep making an effort?