So my girlfriend and I broke up about a week ago doesn't matter why. For this reason I have been scouting some beautiful girls to have sex with or even try to date and the way I have been doing this is by building up my social circle (I'm in college).

There happens to this girl in particular who has been in my social circle for a couple of years, not too great of friends, but good friends. Her dad died freshman year and I was there for her, so she thinks of me as a good person. We have always flirted but I have never made a move because she was a virgin and I didn't want to waste energy pursuing.

Two years later, I rediscovered how attractive she actually is. Cute, works out, easy going, Italian, and a confident fun personality. So... I started gaming her, pretty well. We've been drinking every weekend, going hiking together, and she always asks me if I'm still with my ex, although I have told her a few times before. I believe she finds me sexually attractive, maybe I'm just ego tripping but I'm pretty confident she does.

Now this is where it gets complicated. One of my good friends who happens to be a girl and one of her friends as well, asked me out of the blue if I was into Lizzie (the girl I want). I played it off saying, "yeah of course she's awesome." And she's like, "No I mean do you LIKE her." And I tried to find out why she was asking me and she couldn't give me a straight answer. At that moment everyone walked into the room where we were talking so I wasn't able to find out why she asked me.

Why its complicated. If I go for it and rejects me, my social proof is gone. Maybe I'm just overreacting but everyone will know and I don't want to deal justifying my actions and what not.

I forgot to say that one time when we were drunk, I was caressing her neck, she was facing me, loving it. Then I said.. "I'm not trying to.." then I caught myself. She walked away and disappeared for two hours. I know she wasn't with another guy because the party was at her house and her friends were worried sick.

Should I keep persisting or not fuck with it? Any pointers?

If her friend is asking if you like her, that's pretty much a dead giveaway that you're good to go. I don't see what's holding you back, really. I also don't understand why you think your social proof is gone. Your perception of the situation always shapes the outcome. What's so hard about smoothly transitioning to something more than friends? Don't put all your cards on the table and do something stupid like telling her you want to take it to the next level; instead, get her to go out with you alone more often, and when the time is right, go in the for kiss. It's smooth sailing from there, in most cases.