Little bit of a long story, but I'll cut it short as best as I can.
Ever since I was eight or so, I've had anxiety problems up the wazoo. It made being social really difficult. This past summer, I decided to see a therapist because I knew it was getting out of hand. After a few months and going on (and now off) medication, I've fully grappled with it and feel fantastic. Recently, I've started listening to podcasts and reading articles about pick-up, and now I'm even more comfortable than before. Even my wardrobe, hairstyle, and general body language have morphed into something that I'm proud of.
Going back to February/March, before all that, I dated a girl from a painting class. We had a really good connection, but due to my crazy anxiety, it never got physical in the slightest. I totally pussed out and it's one of my biggest regrets, cause she's really unlike any girl I've met, and I mean that in the most sincere, least cheesy way possible.
Jump back to today, I visited campus for a student exhibit (I just graduated) and I decided to text her telling her to stop by. She was really excited that I was there and came over sooner than I thought. We talked a little and she headed to class. I bumped into her a few hours later and we started talking. Immediately, she's commenting on my jeans; they're a little on the tight side and I used to just wear khakis. I roll into my pick-up game about how she's checking me out, and she insists I look really good in them (a few times, even to another girl who came into the conversation later). When she teased me about a time that I had sex (really funny story for another time) I made some implications that she and I could recreate it. That flustered her.
I isolated her later and we went on a walk, first with her holding onto my arm, then with her holding my hand, just building up Kino like it's no big deal. We talk for awhile and head back to join the others. At this point, I decide it's time to leave while I'm on a good note, and ask her to get a bite to eat tomorrow before checking out another student show. She says yes. Hug goodbye, go on my way (she actually seemed bummed to see me go.)
So I guess my question is if girls are willing to give guys another chance after they've gone through a makeover. Would it be a good idea to try and work up to a kiss tomorrow, or should I keep it friendly because I already preemptively shot myself in the foot?