Backstory:

I'm a 26yo guy. Went through a break up from a 1.5 year relationship 3 months ago and in the last 3 weeks started going on dates again. I've been reading PUA forums and watching infield videos and stuff for probably 6 or so years, and while I've gone through some streaks of success and really cool pulls, I would say for the most part I've struggled with approach anxiety and lately have been getting blown out of sets regularly. 2 nights ago I went on a date with a girl from a dating app and we fucked. Last night I wanted to go out with friends and game.

FR:

Started the night off drinking by myself at my studio apartment, and met up with a friend of mine who's really successful with women at about 11:30pm. He was attending a law school ball after party at a popular bar. When I got there he was sitting with 4 girls in a booth. 2 of them were decently attractive. I met them very briefly then went to the bar for a drink. When I came back there was a spot next to one of the cute law school girls. She invited me to sit and I flirted with her briefly, but overall wasn't feeling it. Looking back she probably had some interest. Later I was sitting next to the other attractive girl from the table. Again, I wasn't really in the right frame to escalate, but gained some social momentum. Another one of my friends met up with me at this point and we left to grab some drinks/shots.

After grabbing drinks, I noticed a really sexy 40+yo MILF kinda eyeing me from the other side of a table we were on. I noted that to my friend. Then after waiting a minute and getting eye contact I opened the set of her and her less attractive, but decent friend. Basically I just stood confidently and raised my hand up to waive, and said "hi, I'm childishgames, what's your name?" Then I asked if the MILF was her sister. I talked for probably 30 seconds, found out she's Brazilian, then introduced my friend. We talked mostly about bullshit, but my key thing I did was maintain strong eye contact and confident tonality. I utilized long silences to escalate the sexual tension with strong eye contact. We were still separated by a long table. She mentioned something to me about how we should go to get food when she's in my neighborhood for her job. I questioned her about her job and she was being mysterious and not telling me, so I gave that back to her by pretending I was gonna say something, then saying "nevermind, I already know the answer".. that definitely made her chase some.

Edit: I'm remembering another thing. She tried to impress me by telling me she just bought a Ferrari. My natural instinct was to be impressed and give her validation, but instead I told her that she looks like the kind of girl that drives slow. I'm not sure if this was a good comment. She didn't laugh. She was kinda offended actually. But she started to validate herself and I transitioned the subject.

Edit 2: I'm remembering that the MILFs friend teased me about my shirt cause I was wearing a bright floral button down. She said that the MILF has the same shirt and it is feminine. I said something like "great shirt (high five the MILF who has the same one).. since I'm a rugged manly man who chops down trees, it's important to contrast that by showcasing my feminine side" slightly teasing myself since I'm a skinny guy

At this point I definitely could've number closed but we split up from the set with nothing and went outside to talk to random people. An hour later we were back inside. We ran back into the MILF set and started to flirt more. Actually, the MILF set happened to run into the first set we were talking to. They were both taking to me, and kinda competing. This was when I really knew I was in a good position. They were repeatedly giving shit tests, asking if I'm a fuckboy, I remember saying she things like "I don't like labels" and saying I love to flirt. She kept trying to impress me by bringing up other guys she's dated. Her friend said I looked like some European guy she had a romance with. I would just say "oh, cool" and talk about something else. Brazilian MILF tried to set me up with the girl from the first set. I talked to her and she wanted it but she was kinda boring. While Brazilian MILF was busy getting hit on, I was flirting with all the girls around me. Eventually, me, my friend, Brazilian MILF, her friend, and some random cool guy (who normally I would let AMOG me) all got an Uber to a notorious MILF bar. In the Uber, MILF kept telling me not to be such an asshole all the time. Smooshed in the back seat, we made out a few times. But I knew things were far from over if I wanted to pull. This was an alpha female type personality.

My friend disappeared instantly when we got to the bar. I got a drink, danced, talked to everyone in the group. The random guy started dancing with Brazilian MILF. Every time she started flirting with other guys, I would open a new set. There was one really cute girl in particular with Bangs that looked like Mia Wallace from pulp fiction that I kept flirting with. When MILF came back to me, she asked about that girl and I said that she's cute and kinda my type. We ordered an Uber back, but while waiting, a random cool attractive European guy got into our group and managed to Uber back to the set's house. So competition wasn't over. On the ride back I was very slightly fingering, but mostly rubbing outside her panties. We got back, we all had a glass of wine, and after that, I went back to the room with MILF, and fucked for a long time.

Tl;Dr - I was way cooler than I usually am. Basically felt like a master PUA all night and pulled a super sexy Brazilian MILF.

Things I did well:

Opened confidently, strong eye contact, used silence to my advantage, passed multiple shit tests by being cocky and pretending to be cooler than I am, flirted with other girls when she tried to make me jealous. Escalated slowly and strategically, utilizing that sexual tension.

One more thing that I'm starting to become a huge believer in is the whole social momentum thing. Not only does momentum carry from one set early in the night to the next, it also carries from one day to the next. By having success on tinder dates earlier in the week, I carried a lot of confidence and momentum into the night.