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how long to wait...
I am usually really shy about asking girls out but I stepped outside that earlier in the school year and asked out one of my newer friends in September that I had just met (friend zone always gets me) at the beginning of the year. She didn't know what she wanted and I was eventually shot down(after a brief "I want to get to know you better phase" which didn't happen) due lack of time/family problems/lots of stress. However something told me it was right and I didn't give up and eventually sent her an email over break asking if we could try it again in the spring. Got shot down again. She said anything she entered into would be more of a comfort thing than anything serious, and it wasn't fair to do that to me. So I said fine, told her if she wanted to try it once things cooled down she had to take the initiative b/c I was done asking, told her I would need a little space for a while, and closed by saying that if she ever needed me as a friend I'd still be there.
Figured it would take me a while but all it took was Thanksgiving break to realize I was just killing myself. When I got back to school, I immediately noticed one of my other friends, whom I've known since we were freshman(college) and spend lots of time talking, playing video games with, etc in a whole different light. She isn't the same drop dead gorgeous as the other girl was, but her personality and who she is a a person is really sucking me in. Is there a time-frame you should wait in between asking 2 girls out so it isn't seen as desperate?
I swore to myself last year that I would not bring in the New Year alone as I have done every other year of my life, and while it's getting close, I don't know if I should push this to end up in a "reboundesque" type of relationship, yet I don't want to let it slip away either