I am in a classic nice guy mess right now. And it sucks.
I am 23 and for a long, long time now, I, an otherwise highly functioning/capable person, have been utterly unable to drum up the courage to ask any girl out. I am not vein in the least bit, but I very often get compliments on my looks from random strangers.
In college, I had a lot of girls just flat out tell me they thought I was cute, or they would flirt with me a lot and smile around me. I had 2 very attractive and intelligent young women in my classes take a strong interest in me without me even asking. In the 1st case, she started talking to me in class and in the 2nd case, she arranged a study date through one of my roomates. Both made suggestions that we hang out, do things, etc, clearly inviting me to come forward a bit, but I never did. Too nervous and insecure, I have very little self confidence and I just couldn't believe that these girls(especially the 2nd one, a gorgeous Abercrombie wearing blonde soccer player who could get any 35 yr old lawyer in town if she wanted to) would take an interest in me.
I really feel like I blew it, especially with the blonde who I was much more compatible with and was much more natural to talk to. I am still in touch with both girls- but one is in DC and the other is in Florida and I am in Boston, so that is problematic.
I have had a lot of stress in life in the last couple years- my Dad got sick and passed away, I have had difficulty finding a job to pay off college loans and I really do not know what to do with the rest of my life.
However, I have come recently to a strong realization that no one is going to be able to change the situation I am in but myself. To that end, I have recently been drumming up the courage to actually take some initiative with girls. I work security at concerts and met a gorgeous girl at the Backstreet Boys reunion show a couple months ago, I gave her my phone number. I saw her again(fate would have it!) last night at the Maroon 5 show, she recognized me right away and I told her later that night that Adam Levine said she should really give me her phone number
Well I got it, and now I have of course realized that its not so damn hard to do, and really, WTF do you have to lose?
So just when I am ready to hit the bookstores or the gym or more concerts or maybe(if that awesome U2 tribute band Joshua Tree is playing) the bars, a girl I work with drops a bombshell on me! I like this girl, she is cute, very nice and intelligent, but she is kind of out there and she really does not do it for me. I can't explain it, but you all know what I mean. I have been friends with her sister and her brother in law(who is one of the higher managers at the security company I work at) for 5 years. We have gone out for pizza together in a group, but tonight, when I thought we were doing that again, her sister left her with me alone. And she was wearing heels to a dive pizza joint
Then she takes the check, wont let me see it, gives it to the waitress w/her card. I protest, and she says " I asked you, I'll pay." I responded "I got next time, then." She says "you have to ask then." I was shocked but said nothing. Manipulative much? I didn't even know it was our 1st date, and she has a cooked up in the middle of the night scheme to get a 2nd date??????????
Anyways, I get home and there is a big long Facebook message from her saying that it was really her way of asking for a date and she can't read me but she really likes me, blah, blah, blah. I honestly don't know what to do now, and I honestly haven't even read the whole damn thing. Just key points, and then I got physically sick. I had the sense she liked me but I was hoping it would stay in the friend zone without getting awkward. Now its super awkward, with the very forward facebook message, the fact that I know her sister and bro in law and that he is one of the managers of a company I have worked for the past 5 years. And I met U2 because of this job!!
So now I would of course, being a nice guy and all, feel like a jerk if I rejected her or gave her some run around that amounted to "lets be friends." Plus, going to work would be awkward, which I never wanted out of a part time job that lets me see shows and have funny stories of hauling drunk assholes out of concerts.
But now that I am finding out that getting numbers and putting yourself out there really isn't as hard as I cracked it up to be, I don't want to settle for something that wont satisfy me in the end. I know I can do better, I was given open invitations that I was afraid to respond to by better quite frequently in college.
Granted, there is definitely a bit of selfishness and bitterness involved here on my part. The way I look at it is(and this is unhealthy) I had numerous crushes and desires in the last 8 or so years and I just shut my mouth, so why should I just cave into the 1st person who is forward enough when its not really what I want? Why should I give what I never got myself? I never walked up to the super attractive, super nice, intelligent volleyball player that I had a crush on and said "lets have a date, I need to know right now do you like me, I really like you, etc" just because we had friendly conversations and smiled at each other.
Sorry x1000 for the long post, and here is a cliffnotes summary:
I think a girl I work with is freakin infatuated with me, she has basically said as much and demonstrated this through her actions, and I am such a cliche nice guy that I am afraid about how her and everyone I work with will take a "lets be friends" answer.
Desperate for advice here. This is where I go when my friends aren't up to call, I trust the intelligence of fellow U2 fans!!
Seriously, thanks in advance to all!