6 Mistakes That Kill Your First Date

And also, what to do instead.

Jessica Wildfire
5 min readJan 11, 2020


One of my worst dates showed up in a baseball hat and denim shorts. He corrected me three times, insisted I was an amateur writer, and then left early to have dinner with his mom.

No, wait…

My worst date tried to finger me on his mom’s couch while she was putting away the dishes.

“My mom’s cool with it,” he said.

Actually, my worst date was probably the one where he brought a guitar. Don’t ever bring a guitar to a date. Of course, I’m forgetting the date where someone tried to convince me to howl at the moon with him. Maybe I’m being a little judgmental here.

You know, all of those dates sound pretty bad.

Surely you can do better.

Let’s flip things around for a minute. It’s not always the guy. I’ve also been the problem on a lot of first dates.

I’ve tried too hard to sound smart.

I’ve tried too hard to come off as funny and adventurous.

I’ve tried to be what I thought the other person wanted, and that always ended in disaster.

The worst time I screwed up a date — I bought an obscure painting for way too much money and hung it up on my wall. He was working on an M.A. in art history. When he arrived, I showed him.

I wanted to impress him.

He tried to admire the painting for a few seconds. Then he asked, “So it looks early 20th century. Who is this?”

I stuttered for a few seconds. Then he laughed. “You bought a painting, and you don’t even know who the artist is?” My face went red, but he didn’t notice. I’m so pale, disgrace looks like a mild blush.

Guys try to impress girls for sex. Girls try to impress guys to keep them around. In the end, he didn’t hang around. It’s a little humbling to know that you’re someone else’s worst date story.

The first date always causes the most stress. It feels like an audition, or a job interview. You don’t know how to act. And that advice, “Just be yourself” doesn’t help — at all.