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tell me about the worst date you’ve ever been on!

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While I’ve had my share of dates (many years ago, now), I can't think of any that felt truly unsafe or awkward. And I know that women often have all sorts of safety measures in place before going on a date. So my story isn't going to be nearly as bad as some if not most worst dates.

All that said, I enjoy small talk and see dates as a chance to perfect my game. And, since I had a rule of only staying on first date for 90 minutes, one particular date does come to mind—more of a funny story than a disaster, and a very DC kind of story.

I was newly single and working at a think tank in DC. One night, I was out with friends when I noticed a woman at the bar who kept glancing my way. I was feeling a bit low on self-confidence, so I basically pulled a “Night at the Roxbury” moment: "Who, me? No, him? Me? Nah, it's cool." I decided to play it cool, anyways, and headed to the bar. She took a spot next to me and introduced herself.

Now, this bar was definitely not a first-date kind of place. It was more of a "dollar Miller Lite until 7, then a dollar and a quarter until 8" sort of joint. You get the vibe.

I gave her my number, fully expecting never to hear from her again. But three days later, I got a text from "Pour House Smart Girl." I won’t pretend I was classy after those dollar beers.

She suggested we meet up, so I picked my favorite first-date spot—RIP Cafe Soleil. The conversation was going great, and I usually avoid asking "what do you do" right away, but eventually, I asked.

She told me she worked at a think tank, and when I asked how long, she said, "Since '02."

“Cool, like in policy?” I asked.

“No, Comms,” she replied.

That’s when it hit me. The think tank she worked at was pretty much responsible for the PR push behind the "weapons of mass destruction" narrative in Iraq—the yellowcake stuff, the whole lead-up to the war.

“Comms, huh? Since '02?” I asked.

“Yup.”

“YOU TOOK US TO WAR IN IRAQ!” I blurted out, probably a little too loudly, all but calling her a war criminal.

“Uhhh...sorta, I guess,” she said.

We dated for a few months. She was great, but we were just in different places. I was a late-20s guy going on 13, and she was a late-20s woman going on…well, whatever age she was going on to, probably about to buy a house on her own or something.

And that’s how I learned to stop worrying and love the bomb.

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great punchline!

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Aug 15
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join the club!!

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