Dating Diaries: My Big Bold Move (Thank You, Wine)

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As we’ve previously established, I’m shy. I’m bad at flirting, for whatever reason. But one of my New Year’s resolutions was to “Be less passive,” so I’ve been trying to push myself to take more risks when it comes to talking to men I find attractive. And this week, thanks to some elementary school combination of dares and wild encouragement, I was actually kind of bold.

I was at dinner with a bunch of colleagues and friends the other night, and we were drinking wine. (The wine is important to the story.) Most of the women at the table were not single, so although we were all enjoying flirting with the bevy of good-looking waitstaff, it was largely on my behalf. Friends are the best.

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When a gentleman came over and pointedly asked to refill my glass, everyone agreed that he was flirting with me and encouraged me to get some digits. Not just that guy’s digits, but another waiter’s digits as well. Err’body in the club getting digits! Like I said, there was wine and everyone in the room was unusually attractive.

So I tore a piece of paper in half, and wrote my name and number on both pieces. I was afraid that the men would talk about it in the locker room afterwards and think I was slutty, so one friend suggested I give them different names. I crossed out my name and wrote “Rachel.” Then I realized that I could not believably cross out one name and write another, and I could also never date someone who thought my name was Rachel through the fault of my own lie, so I threw that half away.

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Feeling brazen, I strode up (probably looking at the floor but whatever) to the flirting waiter and said, “Hey, cute boy.”

Him: “Hey, pretty lady.”
Me: “I don’t mean to sexually harass you at work, but this is my phone number.”
Him: “I’m going to use it!”
I might have responded “Yay.”

He seemed genuinely excited that I gave him my phone number. I was genuinely excited that I had suddenly become a brave dating champion, and also because he is cute and now has my number — which he did use later that night to say hi. That’s about as happily ever after as it gets around here, so lesson learned, at least for the next three days: just go for it. Maybe next time, just go for it without the help of two glasses of wine, though.

Nikki Metzgar is a writer from Texas. She thinks the best first dates don’t include sit down dinners, but can’t help but be impressed by flowers. @nikkimetz