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30 Days of Online Dating: How Soon Is Too Soon?

02/27/2015 04:46 pm ET | Updated Apr 29, 2015

This is a modern dating experiment. One girl. Five dating sites. Hundreds of chats. Thirty days. Thirty dates. Eighteen guys. (?) boyfriend. To start at the beginning, click here -- or jump right in at date nine below.

Date 9/30: Tinder Oliver*

My second date with Tinder Oliver. Our first had been a lovely evening of drinks at Chateau Marmont just four days prior. Four days in which I managed to go on five more dates with five other men. I have never been so tired of talking about myself.

Despite my exhaustion, I am quite excited for the evening at hand -- an Arctic Monkeys concert at the Wiltern. TO knows I spent the afternoon at the fair, though he doesn't know it was a date. Somehow I felt like that might have been a bit of an overshare.

TO: I hope you are eating weird friend things. Set time is 945. Want to meet for a drink beforehand? 830ish?

Perfect. I proceed to pass out on my newly acquired, enormous stuffed Nemo for an hour before pulling myself together.

I'm strangely nervous as I tip-toe into the Beer Belly, meekly joining Tinder Oliver at the bar. He's got a great rapport going with the bartender, which I take as a good sign, personality-wise. We chat the fair, Breaking Bad, and music, with me stumbling over every third word and confusing half my facts. Pretty sure this experiment is destroying brain cells by the thousands.

Seemingly unfazed by my flounder, Tinder Oliver gathers my splintered proclamations in one kindly swoop after another, adding his own intriguing insights to the heap. How kind.

We trek over to the Wiltern, grab a couple cocktails, and settle into our seats for a delightful show -- bras thrown onstage, half-naked streakers and the like. I take this time to showcase a few of my Taylor Swift-approved, shoulder-heavy dance moves. TO pretends to be amused, which I decide to take as another good sign.

Post-concert, we slip into a dive bar, where I insist upon a darts sesh. TO warns against this move, as the game of darts just so happens to be his special secret talent.

TO: Choosing a different form of competition will be much more fruitful, I assure you.

...

I throw some cash on the counter.

I lose. We keep playing until I lose less badly.

Our fellow patrons are a touch rough and tumble, but remarkably welcoming. One man requests a photo with me. Another attempts to hop in our game while Tinder Oliver is in the restroom. A third won't quit asking how tall I am. Seriously, won't quit.

Irritated and tipsy-verging-on-tipped, I turn to him:

Me: Do you know how tall you are?

He nods.

Me: Then don't you think you could make an estimated guess?

...
...
...

In my head, I started with 'estimate it' but then switched to 'educated guess', and I ended up lost somewhere in the middle. Grool. Tinder Oliver gently cups my face in his hands, laughing while correcting me. Great. Now he thinks I'm an idiot.

Five minutes later, he's making out with my face. Guess that dumb girl act really does work? Also, why do I get the distinct feeling that he feels like we're slumming it.

We continue this act out by my car with a lovely little eighties style, hand-in-the-back-pocket makeout sesh next to the meter. Because everything I learned about dating, I learned from a Calvin Klein ad.

TO had taken the Metro there, so I give him a ride home. Downtown. When I live in Beverly Hills. I really have lost my mind. This is where things start to unravel, courtesy of my Spotify starred list. Any façade of cool I had manufactured vanished the second Jennifer Paige's voice came blasting out of my speakers. Followed by a who's who list of late nineties one (barely) hit wonders.

TO: Seriously. WHO are these people?

...

As I pull up to his place, I secretly wonder if he's going to invite me in - not that I would accept if he did (Hi, Mom). Just, you know, curiosity.

He doesn't.

Note to self: Hold off on the Spotify shares until at least the third date.

*Not his real name