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The Worst Date in DC: Discussing Machiavelli With “More of an Ass Man”

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

In 5 Reasons 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: Government employee, 22
  • Lives: North Dupont
  • Is: Female
  • Relationship history, in one word: Too-Young-To-Be-This-Cynical

On a date with:

  • Does: Data analyst at a think tank, 27
  • Is: Male

So how did you meet him?

We chatted on Bumble back and forth for a little while, comparing our experiences as athletes at liberal arts colleges. He asked me what my favorite drink was, and when he discovered I loved scotch, he suggested we go to a scotch and cigar bar. He recommended the place, and we agreed to meet on a Sunday night.

Where did you go?

We went to Civil Cigar Lounge, which I hadn’t been to before. Despite the bad experience with him, I’d definitely go back.

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

1. He showed up on a hover board. When I asked him about it, slightly sarcastically, he replied, “Well I used to walk around, but the streets here are just so dirty that I’d ruin all my Gucci loafers.” I should have just left then.

2. He ordered a cigar while I was still looking at the menu of options. When it arrived he held it out for me to taste. He told me to lick the tip of the cigar to see if I liked the flavor of the wrapper, and then told me that would be the only time he’d tell me to “just lick the tip.” I declined.

3. We got into a conversation eventually about our favorite modern political theorists. As much as I enjoyed reading The Prince, I wouldn’t refer to Machiavelli’s work as the “guiding principles of my life.”

4.  Once he was three scotches in, he told me that I was really lucky to be on this date with him. As he informed me, he’s really an “ass man,” and couldn’t tell from the pictures on my profile what my butt might look like. As he is “in his prime” he has the opportunity to be very picky about the women he goes out with.

5. When we (FINALLY) left the bar, he started riding the hoverboard and offered me his hand. He actually wanted to hold hands with me while I walked and he rode the hoverboard. I declined and ordered an Uber home. He then tried to kiss me before my Uber came, and I pulled away. Clearly he didn’t take the hint because he texted me repeatedly (to no response) for the next few days. I think he eventually figured out that I might not be that interested, and I eventually deleted all of my dating apps.

Went on a date that tops this? Send it to us at 

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.