Ok, so I have worked with this girl for a few months now. We've been friends but only recently got a little closer and started talking about our relationship woes. She's always flirted with me and the other guys that work here but recently (she also just broke up with her boyfriend who she has been with since I've known her) she started being more flirtatious and physical. I've always had a small thing for her but never really had the chance to do anything about it.
So, I only found out that she was single after she was asked out by some guy in her class. She was telling me about how excited she was and asked me all kinds of questions about what X or Y meant, but was really only worried that he might not call. I half-jokingly said that if he didn't call, I'd take her out to dinner, and she smiled and said she'd hold me to it.
This guy was supposed to call her around 7 last night and ended up texting her around 6:30 saying, "Sorry I had to go home to help me dad with something, I'll see you in class tomorrow, maybe you'll let me reschedule." Obviously she was sad and bummed and thought he was lying, she'd also gotten all dolled up and excited for nothing.
So, when I saw her at work today the first thing she did was hug me (I'd had kind of a mediocre experience with a girl I was also interested the night before as well and she knew about that). She asked me if he was worth seeing again but I didn't want to sound biased so I didn't really go off on the guy like I normally would have. Instead I just said it was a real jerk move to make. She said that he'd apologized and asked her out for "coffee" today and she turned him down. She mentioned that she hoped she would at least have a date for this weekend.
I feel like this is my chance to finally go for it, but I don't want to make things awkward at work or ruin our friendship either. Valentines day is coming up soon, and she has her 21st birthday soon after that. I'm not sure if I should go for it, wait, or forget it altogether. Any opinions?
but, I just know that I'll regret it the rest of my life if I don't at least take a chance. "