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The Worst Date in DC: Getting to Know a Circumcised Comedian Over Drinks

5 reasons why dying alone is probably better than going on this date.

In 5 Reasons Why Dying Alone Is Probably Better Than Going on This Date, we ask anonymous Washingtonians to chronicle their tragic attempts at romance in the city. On Fridays, we put it on the internet. This week:

  • Does: PR, 35 at the time
  • Lives: Alexandria
  • Is: Female
  • Relationship history, in one word: inconsistent

On a date with:

  • Does: Works for a defense contractor, 39
  • Is: Male

So how did you meet him?

Late night at Lola’s on Barracks Row (now closed). We exchanged business cards.

Where did you go?

Elephant & Castle on Pennsylvania Ave for drinks and appetizers.

What are the five reasons dying alone is probably better than going on this date?

1. About three sips into my first glass of wine, he told me he was circumcised. I did NOT ask, nor were we discussing this subject whatsoever. Making matters worse, he further clarified the meaning of circumcision: “As in, I don’t have any extra skin on my manhood.” Yep, I got it.

2. In high school, he and his friends made a bet about who could bring the hottest date to prom. No one thought he had game, but he showed them all by asking a popular girl to the dance. She not only agreed to go with him, but she also wore a skin-tight red dress. He won the bet!

I wondered why he wanted me to know this story. Soon his rationale became clear: He’d recently reconnected with his prom date on Facebook. He then proceeded to read aloud a recent (lengthy) text conversation between the two:

“So I said, ‘do you still have that red dress,’ then she said, ‘of course,’ then I said, ‘I bet you’re still hot,’ then she said ‘you always were a great guy.'”

This went on for 10 minutes, at least.

3. He and his friends have group text battles where they compete to see who can send the most offensive pictures. At first I was like “whatever, that’s totally a guy thing and no big deal” but then he scrolled through all the texts to show me the truly disgusting pictures, all while he cackled with laughter. I was horrified.

4. “I’m a comedian!” he reiterated several times during the date. Fair enough. Perhaps I wasn’t his target audience. Case in point: He proudly told me about the three “legit stalkers” he’s had throughout his life. Then he looked me square in the eyes and said, “I think I’m ready for another one.”

5. After the date, he offered to walk me to the Metro. I agreed. During our walk, my dress blew in the wind and I noticed him check out my legs. It was awkward so I made a comment about my super-pale legs. He said, “eh, I’m not a leg guy anyway.” I said, “What kind of guy are you?” He said, “I’m a vagina guy.” Set myself up for that one.


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Staff Writer

Elaina Plott joined Washingtonian in June 2016 as a staff writer. She has written about her past life as an Ann Coulter fangirl, how the Obamas changed Washington, and the rise and fall of Roll Call. She previously covered Congress for National Review. Her writing has appeared in the New York Observer, GQ, and Harper’s Bazaar.