TLDR at the bottom, but it's a good story.

To start, I am not ugly, kinda look like Finch from American Pie. Ok, maybe I'm a little ugly. But I am very confident and have no issue talking to almost anyone except hot chicks.

So my city has a big festival that happens this time of year where people can put out their pieces and they get voted on and eventually someone wins $5,000 for it.

My catch didn't happen until Saturday night, but I'll start on Friday. I went out and sat at my favorite bar where I know the bartender very well. We joked about me pretending to be one of the people that were in the festival so I decided to give it a shot after about 3 beers. I went and I found a piece of art that I liked and seen a girl standing buy it, I said "This picture was painted by my brother." and her response... "So your brothers name is Molly?" I was caught off guard, tried to recover and failed miserably, but it made me realize I had to put a lot more effort into this. I found a painting by a male and started handing out business cards that were laying near it. I was saying I was the artist and being way funky.. just off the wall didn't give a crap trying to get anything to stick. Low and behold the artist shows up and he's a real nice guy. I tell him what I was doing and he started laughing and we hit it off pretty well. Then we banged. Jk. But, he decided to help me. He was from a different city and had never been in my town other than passing through.

So, my attempts evolved. I went from being his brother to being his good friend and telling people I was an asshole and his art was great. I was jesting my self and making people laugh. I had about 3-4 times when I felt I could have closed and been doing well but it just wasn't comfortable and I knew it. The night was winding down and not many people were coming through for the show anymore, so I asked him if he'd ever been to a club. He never had so we went. The bouncer wasn't going to let him in, he wasn't from around here and he had a back pack. I explained he was an artist and it was his first time at a club, they went through his bag and let him in. We had fun, drinking beers watching and engaging with women. This guy was a complete beta but was grabbing girls attention with his artist badge and they tell me he was really sweet. Bah. Gtfo of here. Anyways the night was getting a little rough on me, I was too drunk to continue and way over my limit I had set so I walked home.

The next night, I meet him there by his painting as planned at about 6 PM. I told my self I was limited to a beer every 2 hours or so that way I didn't tire my self out. I'd drink a water in between each and we started on the same thing. Me trying to get him votes and just hanging out having fun coming up with wacky pick up lines. I maybe talked to 800 people both nights combined... 20,000 attend this festival every year. Again the night went on until club time, about 11 PM. We went up and got in easily, no back pack. We started out front of the dance floor and drinking Corona light. We danced with some bachelorette party girls and had a good time. I'm pretty much the entertainer type and like to see people laugh, so I engaged the guys obviously trying to pick up other girls and had them dance with them and we all had a good time daring each other to but into girls only groups. It was about 12:30 maybe 1 and I decided I had enough of being rejected, dancing with girls that hated me and being a laughing stock. I made my way to the exit directly through the middle of about 80 people on the dance floor, as I'm walking out and about to exit, I say in passing to a girl "You look like you don't want to be here" It was the realest thing I had said all weekend. She responded "I don't" and I said, do you want to get out of here? She responded yes and I grabbed her hand until we got out of the crowd and we went back over to my bar. We laughed and talked to the bar tender until her friend texted her and came over. I had to go take a piss and when I got back she was writing her number and name on a napkin for me letting me know her friend wanted to leave. I told her I'd text her so she had my number too and so I did.

That was it. I've got a date with her on Friday and she seems really into me so far from texting. So wish me luck on the date.

TLDR: I talked to thousands of people that night. I was rejected 100's of times over the course of 2 days and then I talked to one girl with a real stupid passing sentence.. and it worked. I didn't even mean to talk to her.. I didn't think I was going to and I had given up.