Dating, Dating Challenge, NYC, Online Dating

“I Can Almost See Your Boobs”


Date #1

A dive bar on the UWS. Public, casual, and taking cues from Olivia Benson, safe for my debut on the online dating scene. And it’s trivia night. So even if this guy’s a dud, I can exercise my Leo competitiveness. My outfit was minimal- black pants, black booties, and a black v-neck sweater that hit just about mid-chest. A bit of mascara and voila! Cute and dive bar-y.

On the way over he texted.

What can I order you? 


Oh. You don’t want to see a cocktail menu?

Nope. Just a Guinness. Thanks!! 

Walking into the bar, I realized I didn’t reeeeaaally remember what he looked like. It’s Day 2 of the challenge and I Bumbled 10 faintly memorable people attempting to sound genuine when they asked why I was so adamant about drinks tonight. I have a crazy busy week ahead of me and this is the only night I can meet! I just prefer meeting in person- texts aren’t my thing 🙂 Is that weird? I probably sound aggressive. Or like someone who would turn into a crazy girlfriend. Turns out, crazy attracts crazy. 

The bar was well-lit and crowded. Found him. We introduced ourselves and, wait, does he have an accent? Yup. A Liverpool native who spent a big chunk of his childhood staying with his grandparents on a (beautiful) beach in Israel. AND he had a solid job in finance.

Cute. Foreign. Clean. Point for me!

Have you ever been on a date where you waste your precious time sitting across a table from someone who masterbates his ego all night? This wasn’t one of those dates. The conversation was great. No awkward silences, nice flowy conversations, thoughtful questions. Also, the trivia happened to be mostly sports-related so we had a few laughs talking about all the things we didn’t know about American sports, or sports in general.

The night was winding down. Neither of us had hinted at a second date but it was obvious we were enjoying ourselves so I knew it would happen. We left the bar and, still standing out front, I pulled out my phone.

I’m going to call a car.

Why? My apartment’s just around the corner. *wink*

Ugh. No! Just stop! Did he actually just wink at me? We had such a nice night, don’t start being an asshole now.

I need to head home. I had a fun night though. 

Me too. You look really nice tonight. That outfit’s really cool- I can almost see your boobs in it.

What. The. Fuck. I just stared at him.

Yeah, I knew you wanted me to look at them. You kept leaning over the table and I really liked it. You sure you don’t want to come over?

I’m sure.

Oh, thank God. That was the fastest pickup ever. I’m b-lining to the car and of course he tries to be a gentleman and hold the door for me, but it’s too late for that, dickwad!


You definitely need to call me soon. We’re going to have A LOT of fun together. I mean A LOT of fun. 

I pulled the door closed just barely missing his head. Damn, I should have closed the door harder. And that was it. Point numero uno for me. I’m in the game now, no turning back. I was just hoping it was all uphill from there. And it kind of, sort of was.

Love always,

Art Babe


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