Sorry if this is a little confusing, I wasn't getting any answers on /r/askseddit so I decided to make this a field report. I added what happened at the bar prior.

In high school there was this insanely attractive, insanely intelligent girl a few years below me in my German class, forever had a thing for her but, she's above just about everything, we'll call her Victoria. Well, I used to be a manager at this skate shop at the mall. Her best friend was one of my sales associates. We'll call her Kaylie equally as attractive and less bitchy.

There are these two bars one on top of the other in the town where I generally drink. Kaylie and I had been texting about what we were going to do tonight because we always run into each other. She's 20 so she can only get into a few bars with her fake. The bar she can get into just happens to be a bar right under the bar my good friend and I, who's also an excellent wingman, drink at.

We are finishing our drinks, and go to the bar. My buddy leaves his smokes and his phone on the table to keep it. Contemplating going downstairs to the other bar after this round. I look over and there are two girls trying to take our table, the end of the world gave a gift.

“Are you sitting here?”

“Yeah, join us!”

She does. My buddy and I talk to her and her friend. Her friend is a downer and doesn’t look up from her phone after various attempts to bring her into the conversation. She’s pre-med; I’m an art school dropout, who is actually doing a really good of starting a career. Our conversation is a bit over her head, and I know she is just waiting on somebody, which is what I often do at this particular bar. Regardless, mere months ago, I would of just given them the table.

Drinks are cheaper downstairs, so I ask my buddy if he wants to go downstairs and that my friend is down there. We go downstairs, grab drinks and a table and I don't see her so we just enjoy the change of scenery. I text her to see if she's there, she is and comes to sit with us.

She explains her date is buying all her drinks, she's a broke college student, and that he's really boring and tells us we should join them. She felt bad asking him for another drink, I give her my card and tell her to leave a tip. I normally don't buy girls drinks but she's been a good friend.

We get over to the table, he's a tattoo artist with a bike, the guy almost dropped my panties. We talked about our common interests, being a web designer, he asked once I get a few projects out of the way if I'd do his website. Kaylie wasn't really interested in him. Last call, I leave, I was waiting around for another girl to call, but she wasn't feeling well. I had a bottle of wine in my car and Kaylie still wanted to drink.

So I get there and Kaylie answers the door flirty. We pop the wine, it was a cheap wine. Tattoo artist is blowing up her phone. She smokes in her garage, where she has a huge picnic table. It's freezing in the garage, I rub her back platonically. She gets close, I slow down, joke that it wasn't working, she says it helps. She scoots closer, head on my chest and my arm around her. I grab her chin and kiss her. She comes alive like a minx and we're on the table, my hand is in her pants, she's on top me. We go on, her roommate walks in on us. Her roommate leaves, we continue in the living room. We're fucking riled up, and then she says stop.

I'm really cool about it, I already know. She says, "Victoria, I don't know...I just...umm...fuck...what am I going to...I just...sorry..."

I put my shoes on and grab my keys. She says again, "I'm really sorry"

I tell her I understand very indifferently.

She seems a bit shocked. I kiss her again, she apologizes. A last time, "I'm sorry I just can't."

She walks me to the door, we briefly make out. I leave. I get home and we briefly chat, I tell her my interest never has been in just Victoria after telling her we should hang out again. She tells me to go bed.

Next morning, I accidentally retweet, her tweet from my phone that says something like "Up till 5, last night was weird." I didn't notice till later.

I text her later the next afternoon, asking if she was alive jokingly. She never responds.

Questions:

  • Where did I go wrong?

  • What could I have done better?

  • What could I potentially do to turn this back around?

  • What are some tips for last minute resistance?

TL;DR Almost hook-up with the best friend of a girl I've had a crush on, text her next morning, nothing

Edit: Clarity