Brief description of me... 26/m, anxiety and self esteem issues up the yin yang, body dismorphia disorder and possibly undiagnosed OCD as well. Everyday stoner. Told I'm good looking but I'm pretty damn awkward in uncomfortable situations. I did OK for myself female wise in university and had a few great flings, nothing crazy... A lot of chances ruined by being too needy without knowing it at all, but I still got by. But like many of you, after leaving school I got in a social rut, my party friends disappeared and there's no asking cute classmates to study anymore. I don't do sports or have super social hobbies. I only recently realized I have to really work on the social skills I'll need to be the person I want.

Anyway, rewind to last weekend. I checked an ad for used guitars on craigslist and found one, pure impulse buy (I don't even play, yet). Meet up with the girl selling it at the mall, to my surprise she's a HB8. We make the exchange and I ease the tension and make her laugh a little. As soon as we shared eye contact and smiles (something I naturally avoid like the plague) I find we both feel comfortable and I have no problem flowing from there. She mentions she's getting rid of it since it was a gift for her ex, and she just "can't have it around", I make fun of her for giving up something because of one asshole. I ask if she'd be down to grab a drink, she accepts and we part ways.

We decide what to do over texting. She says she wants to go to a comedy bar. I agree even though I've heard that's a bad idea for a first date. I keep everything short other than a joke about being a craigslist guy. She wants to keep talking with smilies and haha's every text, I tell her I'm off to do something, then no more texts until confirming on the day of. I fucked this stage up so many times in the past by coming across too needy, thank you seddit for making me aware of that. Fuck texting games.

So, DATE NIGHT. I'm shitting fire all day and barely sleep the night before, going over every permutation possible of how this is going to play out. I tell myself this is good experience even if she bails, this girl is way out of my league anyway, as much as I have to pretend she isn't. I get to the bar 10 minutes earlier than we meet, and it's dead as fuck except for two deadbeet barflies and the bartender. Not my scene at all. I'm anxious as fuck. My instincts told me sit at a table and jack off on my phone until she gets there. But now knowing the importance of how comfortable I appear in the social situation, I decide to sit beside them and shoot the shit. When she walked in I happened to be making them laugh (not difficult, these guys were tanked talking about elton john songs)... she arrives I immediately go over and hug her and joke about my "new best friends".

I grab her a drink, we go sit in a far corner and start talking about ourselves. There are awkward lulls, the worst part was at one point she asks me to tell a dirty joke and I had nothing. But I made a point to just smile and make eye contact during these until she laughs and looks away. Every time she looks back agian after she seems more into me. Once in awhile the barflies across the room are yelling jokes at us and giving thumbs up once in awhile, as we laugh with/at them. I give them props as I walk by to the bathroom, etc. The bartender seems to acknowledge me as the not-annoying guy. "Talk to everybody" is DEFINITELY solid advice.

When people start coming in, we head to a table near the stage as they set it up and continue to talk. No kino except for my knee touching hers, and prodding her hip as she walks. The host gets up eventually and acknowledges us as the "romantic couple" (I guess it was apparent we were vibing) and asks we move up. "...Sure, if that will make you comfortable." I said slightly smug as I move our stuff and lead her over. We're relentlessly the target of their "crowd work" in a room of ~30, prodding us to say it's our first date, etc. I even reveal we met on craigslist, when they ask how I just said "I put up an ad for a dominatrix" and leaned for her to spank me. Totally out of character for me but I was already riding a high, I knew she loved the attention we were getting. I was determined that I wasn't gonna let these Jonah Hill motherfuckers put me on the spot, and I somehow made it through... It was like a second set of shit tests and she saw I passed. I made a point to look at her for every joke's reaction, shared the uncomfortable moments when they were bombing, eventually she starts squeezing my knee every time she laughs or feels uncomfortable.

I ask her if she wants to take off for a walk in the cold... We walk down the street with my arm around her hip. We grab some hot chocolate and talk about the show. I'm expecting a kiss and a second date, but before all that she offers to take me home. The details don't really matter from here, a good start to the date and getting myself in the zone led the way to an unbelievable night.

tl;dr : No sex and growing anxiety for 2 years in a social rut. Go outside of comfort zone for once with a 20yo hb8 and it pays off, using various principles/concepts learned from here. Thanks guys.