TL;DR: I'm inexperienced. I'm going out, making efforts and fucking up, learning from my mistakes, and gaining insights from seddit.

I'm really inexperienced with intentional flirting, courting, dating, etc. I've only had one sexual partner, and that's because she made the initial advance and made it abundantly clear what she was interested in. The job where we met was really nice that regard; the ratio of females to males was quite advantageous. There was another girl there whom I learned was interested in me, just not as forwardly, and one more whom I suspect was also interested in me.

On New Year's eve, I hang out at a house party with a friend I've been infatuated with since I met her. I have a pretty good night. We go to a friend's house to sleep, and I tell her I love her while we are talking, in a platonic sense. Even if weirded her out at all, I'm glad I did it because it's true, and because normally I'm way too reserved with my affections. I need to learn to be more intimate and open up.

The following weekend, already quite late, I decide I'm going to go out and try to get laid, which I never do. I pick up some condoms in the very unlikely event that I succeed, and make my way to an area with a healthy social scene, but by the time I get there, it's closing time, and people are heading out. So I fucked up, BUT I got out of the house.

A while later, I text my friend to see if she wants to hangout before she moves for school. She gives me an ambiguous response. I suggest a day of activities that I want to do that I think she'd enjoy as well, with the idea that it can be downgraded if that's too much. She declined both my initial proposition and the downgrade. Cool, level up in getting a rejection.

I go out to see some bands with a couple of friends, and I do a bunch of sketching, many of which are of the many attractive ladies there. As we're leaving, I go over to one of them who was particularly fun to draw, thank her for being fun to draw, and show her the sketch I got. My friends gave me some props for my boldness. Later that night, this 17 year-old friend of my friend belts out lyrics to a song, and this beautiful girl who's a quite a bit ahead of us stops, turns around ditching the guys she's with, and joins him in singing, after which he gets her number, and our mutual friend steps in as his wingman to help get her invested. It is at this moment I curse my inability to memorize lyrics or sing.

I go out the following Sunday with my buddy who's got decent game, and we go to a club, which is a first for me. I've been to bars before, but not dance clubs. I'm feeling awkward in the foreign environment, but I make an effort. I dance badly a bit, and after last call, I go up and talk to a cute redhead with glasses. It's fucking awkward and didn't go anywhere, but I talked to her. Club closes, my buddy and I hang out among the lingering crowd talking for a while, where he's sharing some of the things he's learned over the years with me before we head out. XP gained.

I go to the same club solo the next weekend. I dance and look around a bit, but it is awkward, and I am lost. I leave the club after if closes, go do some sketching, run into a fellow artist I haven't seen in a while and trade contact info with him. It's some time up to this point that I remember seddit, and start reading some of the information here.

The cashier whose number I had previously asked for and given my number to gives me her number so we can arrange for her to cut my hair. I get to her place, and while she's getting ready to cut my hair, she tells me she's gay, which I didn't suspect at all. She's cool as hell, though, and I hope we become better friends.

I go out to a friend's show. I briefly talk to this cute punk girl whose outfit is great. I do a bunch of sketching. I meet another cute girl while I'm sketching, and I give her one of my DIY contact slips. I post the sketches, and my friend tags some of the people who I sketched, and they get a bit of attention much to my delight. The girl finds and sends me a friend request on FB.

Somebody posts an article about John Keegan by the guy who does Humans of New York on seddit, and it resonates with me. I go out to see some bands on my own. I try to find a new spot to sketch while I enjoy the music, and I see somebody else's sketch supplies at a spot that's just right. I sit next to the empty seat and begin sketching. The person gets back, and it's a lovely young lady. We introduce ourselves, and look at each other's sketch book. I give her one of my contact slips and write my number on it. I'm sketching machine that night. I go up and say a few nice comments to as many of the members of the bands as I can and show them my sketches. At one point, an attractive woman asks me, "Is your name _____?", "Yes, it is!", "I heard from some other people you were doing sketches!" I gave her a slip with my number on it. She added me on FB later on, where I noticed she's got a boyfriend, and that we also quite a few close mutual friends. Anyway, back to the story, I'm still sketching the bands and whatever else catches my interest, and these two girls notice me at work, and we start talking. One of them's also sketching, and she's with her boyfriend. I all of them slips with my number on them. The girl who doesn't have a boyfriend with her playfully says "draw me like one of your French girls" to which I show her I already drew her, which excites her. In hindsight I should've been asking for numbers, but I was more comfortable giving out my number, and I had a great night. XP gained.

I go back to the dance club solo. Again, awkward, but this time I do attempt to talk to people. It doesn't really lead anywhere. After the club closes, I talk to one of them again out front and make some jokes and get her to laugh. I ask for her number, but she says she's got a boyfriend. I have my doubts, but whatever, I tried, and I haven't got the chops yet to roll with that punch. XP gained. Level up.

I'm out watching fights with some friends, once again sketching (noticing a trend yet?). A lady sees me sketching, asks if she can see my sketch book (yes), and if she can show her friend (again, yes). Her friend challenges me to draw her right there. Challenge accepted. I draw her, she offers to buy it, I sell it to her, and then I ask for her number, but she's with her boyfriend. I smile and tell her I had to try. Later on, I'm standing on a corner trying to decide whether I want to go elsewhere or head home when these two girls approach, and one says to me, "Hey, Fanny Pack, what've you got in there?" (yeah, I rock a fanny pack like nobody's business; sketch books don't fit in pockets very well, ya know)*. I tell 'em I've got a sketch book, let them see it, tell them my night's going well due in part to selling a sketch. She wants a sketch, but they haven't got any money, but have got some kiwis. I sketch them for some kiwis and ask for their numbers. Only one of them has a number currently and gives it to me. I send a text, and she says she'll text back, but she doesn't. I get a pass for an advance screening of 'The Grand Budapest Hotel', send a text asking if she likes Wes Anderson movies, get no response, and I write her off. Now I've got kiwis that I won't be eating because they fuck my teeth up. XP gained.

*I take it off and leave in my car at the dance club, but I rock it pretty much everywhere else.

So my game sucks, but I'm putting myself out there and fucking up and learning, and coming back here to gain more insight, so that I can fuck up in new ways and continue to learn from my mistakes.