Totally blunt here: I'm terrible with women. Terrible, terrible, terrible. I've had one girlfriend, ever, and nothing much beyond that (I'm 26). Now to the point.

I'm on OKCupid because I have trouble just meeting women so I figure I'll use it as a stepping stone. I've gone out with 3 girls so far; one turned out to be crazy (despite me really liking her), one I just didn't have any romantic interest in, the latest one was last night. We've messaged each other off and on over the past week and we went out to get drinks last night.

For health reasons I don't drink often but she wasn't aware of this. We meet up and I give her a flower that I had for her; I don't know if I'll get flak for this but it's something I use as easy conversation fodder. No roses--I stay away from those--but something seasonal and unusual (and cheap). She says it's sweet and shows it to her bartender friend. She's kind of possessive of it but does show the people she knows that it was given by me (not sure if good/bad).

I'm socially awkward usually so there are some odd times of quiet, etc. She knows EVERYONE at the bar because she is there often. A few times she has some conversations with others. I try to keep up but some of it I really have no part of. She does invite her roommate out with her who shows up ~90 minutes into drinks. She told me that she might do that because 1)I'm basically a stranger to her and 2) he is leaving for Iraq on Saturday morning and she wants to spend some time with him. I'm okay with this.

Despite my shortcomings I think I did okay through the evening. I made more smalltalk than I usually can muster and she gave me her attention through ~75% of the encounter. If there was something she and her roommate talked about she included me and would explain inside jokes, etc. I got her to laugh at some of my stupid shit, she was forthcoming with some private information, etc. etc.

I'm not usually a touchy person but I did make contact with her a few times...I'm really making an effort on this aspect of socializing. I touched shoulder, held her hand when commenting on an interesting ring she was wearing, had my leg resting against hers on the bar stool. At one point she hooked her elbow with mine to walk through the bar. I didn't go in for a kiss or anything but she did give me 5 hugs, 2 of which were as we were saying good night.

The "after date" is usually where I think I screw up the most. Normally I text too much, chatter, and basically beg (though not literally) for followup dates. Last night all I did was when I got home I texted a "thanks for coming out, she was lovely and I had a good time, good night." Today I haven't texted her at all though I did invite her as a friend on Facebook; last night she specifically mentioned FB and her liking it so I thought that was fine. She accepted my request but I haven't gotten any other responses from her.

Based on that should I have a chance at a followup? My plan was to wait until tomorrow afternoonish and text her something along the lines of "I know your roomie left this morning, but I was going to play pool tomorrow night and I'll help keep your mind off him" or something.

To be honest this girl is gorgeous and really just out of my league...but I want to try. Mostly I want to see if I can get her. If not...ah well.

Side question: How do you get a girl to think you are busy and socialize when you actually have no friends and don't do anything?