Me 23, her 22. I met her a few weeks ago at a happy hour with some work friends. She is the roommate of a coworker of mine. As the night goes on, everyone starts peeling off, but she stays. We hook up at various bars, but I do not spend the night. I decide I want to hang out with her.

BTW I'm new here so some of my offenses may seem very obvious.

I text her a few days later on a Friday wondering what she is up to that weekend. I was pretty passive because I got the feeling she was pushing my attempt to hang out away. I simply was acting like I was wondering what she was up to the weekend hoping she would have something she would want me to come to. Pretty lame on my part.

The next Tuesday, I ask her if she wants to go out with some work friends again the next day. I told her should be fun, you should come. She said she would after her work function if it got out early enough, but her roommate told me she wouldn't be able to come.

Ok, I figure I'll just scrap this. But I see her again randomly, and we hang out in the later part of the night and we go back to her place, we hook up a little. I asked her about what happen the week before, and I believe (I was drunk) that she was like, "you invite me to these group things, just ask for one on one". I think... I also learn she is leaving town for a long while in a few weeks, so I feel a sense of urgency.

I guess I gear up for another attempt and last night (Friday) text her "what are you up to tonight?" I dont get a response till 3 hours later at midnight-ish and she tells me she was out, and asked what I was up to. I didn't respond.

I somehow ran into her roommate earlier in the night (before the girl responded) and was like, "yea what was X up to, I texted her" and the roommy goes, "oh you" essentially.

So, I have to admit, I am/was a little embarrassed.

I have put myself out there 3 times and each time I got similar responses. I realize my approaches were weak. I wanted to invite her out for some Cinco de Mayo fun but it's with nonwork friends (not sure why the group thing actually makes it difficult for her...i guess more pressure on her and i'm a noob) and it's short notice. What can do I about that? And/or should I just give a more direct approach to get her to hang out 1 on 1 this week for drinks? And I still haven't responded to her text from last night too. How do I approach taht one?

Also, she gets self conscious about her and dudes when her roommy has been around.