Ramblings about girls and stuff

I just briefly saw the girl whom I have considered asking out in the past. She is a friend of my roommate, and I see her periodically when he has a party or get-together. Really nice and pretty and into music, but I can't tell whether she has any interest in me. Of course, I would have enough trouble asking her out due to my shy nature and lack of self-confidence, but now this Confusion with a capital C is weighing heavily on my mind as well.

The only girl I ever sorta kinda asked out was another friend of my roommate's that I met at a party (my roommate has got to be the most social person I know, I really admire the way he is able to maintain so many close friendships while at the same time going towards his masters, working, and being in a serious relationship). This girl was beautiful, funny, and a fan of classic rock, which is icing on the cake. My roommate encouraged me to ask her out, but I chickened out of course. However, I decided to try to salvage the opportunity and I asked him to ask her if it would be okay for him to give me her number (phew). She said yes, and I finally worked up the nerve to give her a call. She was living about an hour away at the time, near where my cousin was living, so I asked her if she might want to hang out when I came up to visit him. She said sure, but that it couldn't be a date-date since she was seeing someone (D'oh!!). That discouraged me a bit but I said that was fine.

We made tentative plans to hang out, once she finished studying for a test. At one point she gave me a call and asked if it was okay if some of her friends accompanied us. I said okay, though I didn't like where this was going. Next thing I hear from her, she tells me she still has a lot of studying to do, maybe some other time. Suffice it to say I was very discouraged after that. I never tried giving her a call again after that (stupid of me, probably).

This incident demonstrates two of my worst flaws that I've struggled with. 1) I am overly concerned about what other people think of me. 2) I have a hard time imagining other people finding me interesting. One of my favorite quotes is from Charles Schwab: "A man who trims himself to suit everybody will soon whittle himself away." Well, I think I'm guilty of that. My concern about what others think of me makes my priority to be well liked by everyone, but in doing that I pretty much sacrifice my own personality. Hence my quiet nature. So in a way, # 1 above leads to # 2. My other roommate is a good counter-example. He's very outgoing and puts on a show of confidence and cockiness. There have been many people who find him irritating (heck, I did at first). But those who like him really like him. Maybe the case is that in order for some people to have strong positive feelings for you, others have to have strong negative feelings for you. I don't know. Anyways, it's late and I'm sleepy.