What I Learned From My Worst Date Ever

When you see red flags, trust your gut.

I don’t generally go on First Dates.

“But you love dating!” a girlfriend said to me over coffee just the other day. “You love going on dates.”

And she’s right in that I like spending time with people I’m interested and invested in. I’m most always in the mood for coffee, cocktails, and conversation.

But there’s something about the conventional practice of the First Date—slicing time out of my schedule to accommodate someone I barely know, awkwardly fishing for abbreviated histories and shared hobbies at a restaurant I’d probably never eat at otherwise—that frequently leaves me wanting to curl up on the couch and take a sick day instead.

As someone who has always believed that the best connections develop in more natural ways (which, for me, has usually been getting to know someone through gatherings with mutual friends and then gradually pairing off), I’m apt to choose a variety of other activities over feeling out of my element making small talk with a stranger.

Until one night, when I didn’t, and it was simultaneously one of the most excruciating and most invaluable nights of my life. This is that story.


I met my Worst Date Ever at a friend’s birthday dinner. It was Halloween weekend and the guy peeking at me through a turquoise blue mask seemed very, very cute. After dinner, our group ventured past a menagerie of crowded bars and dance clubs before finally settling on a hookah lounge. The masked man and I sat on a sunken-in faux leather sofa straight out of dorm life and spent a good hour talking before he stood up, peeled back his disguise, and kissed me through a stale cloud of smoke.

I’ll fast-forward through the part where he smooth-talked his way into getting a ride home from me at the end of the night, the part where he tried to lure me into his apartment with a copy of Suicide Kings because we had briefly talked earlier about Christopher Walken, and the part when I turned down his movie et cetera offer and he delivered a series of lines in protest creepy enough to make Robin Thicke blush as I shuffled, grimacing, toward the door. A few days later he asked if we could go on a proper date, and liberal with second chances, I found myself making arrangements for the following week. Nevermind the innumerable red flags flapping in the breeze. 

He took a seat next to me at the bar of a local Italian restaurant where I had been waiting after work, ordered a vodka-tonic, and immediately voiced his displeasure at my pick for the evening. My suggestion to go sit in a booth was hastily dismissed, as he clearly preferred to jeer at the sports on the TVs. Nose in the air, sneer across his thin lips, he reminded me of a villain in a western melodrama. I wondered why he didn’t have a mustache to twirl.

Every line dripped from his mouth like oil, slow and premeditated, like he was rehearsing a play. I learned that his life at 31 years old was little more than a half-assed 9 to 5 followed by a blur of cocktails and one-night stands. It’s a tough call, but my favorite part of our conversation was probably his declaration that “Monogamy just isn’t for me.”

It turned out that we had someone in common. His best friend was a classmate I knew from college, also an English major, and my clearest memory of him was the time he dropped a pencil near me just so that he could squat down and look up my skirt. So much for meeting people through mutual friends.

“I hate this place,” he said again. “What do you say we go somewhere else? Downtown? Or, you know, we never did watch that Christopher Walken film…”

This wasn’t a date; it was a formality. I checked the time. 

“I don’t think I’m going anywhere else after this,” I said. “I have to work in the morning and it’s a half-hour drive home.”

A ridge formed between his brows. He finished his drink staring angrily ahead, slamming his glass down after every sip, never once turning his head in my direction. With a snap in the air, he signaled for not our check, but his check. I slapped down a ten for my wine and turned around to see him already halfway out the door.

By the time my coat was on and my keys were in hand, he was on the other side of the parking lot, unlocking his car. 

And the story doesn’t end there. 

Because the next morning, this grown man who had stormed off in silence felt it necessary to follow up with a text. “You and I weren’t on the same page,” he lamented, “Why did you waste my time?”

If the saying that sometimes you have to hit rock bottom before rising up again is true, then this unmasked man-child was the hot, callous inner core that taught me many things. I learned that Neil Patrick Harris’ sleazy sitcom caricature actually exists in real life, and that some people do not hide their jackassery under a bushel: They let it shine for the world to see. There’s nothing like a flashing neon sign to take all the guesswork out of dating.

I gained a new gratitude for that the company I keep—male, female, straight, gay—who would never treat another person that way. I learned to refine the art of patience with myself and others. I also learned to be more forgiving, to overlook the small stuff, but to only save second chances for those who deserve them. I became simultaneously reassured of the good in people and more inclined to seek it out in new relationships.

Most of all, I learned to trust myself more, to listen to that voice of reason whether it’s whispering or screaming. There are nights better spent reading a book at home and there are nights when it’s time to slip on a dress that makes you feel awesome and go get ‘em, tiger. Because when there’s chemistry, compatibility, and kindness, it doesn’t feel like a chore at all. It feels like fun, it feels like stomach flips, and it could, at any moment, feel like love.

Chelsea Cristene is a community college professor of English and communications living in central Maryland. She writes Gender on the Rocks, a blog about gender, relationships, culture, education, and the media. Find her on Twitter.

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