I’m sitting on my couch in Bushwick right now, it’s 1:17 a.m., there’s a half-eaten bag of Takis turning my fingers radioactive orange, and honestly? Perfect time to trauma-dump about the things to never say on a first date because I swear I’ve said every single one like a walking red-flag factory.
Why I Even Know These Things to Never Say on a First Date (Spoiler: Pain)
Last Thursday I was at this dimly lit wine bar in Williamsburg—fairy lights, overpriced natural wine that tastes like feet, the usual—and halfway through the date I heard the words leave my mouth like a car crash in slow motion. So yeah, here’s the list I wish past-me had tattooed on the inside of my eyelids.
1. “So how much do you make?”
I said this exact sentence in 2023 to a guy who turned out to be a trust-fund crypto bro. The silence was so loud I heard the bartender drop an ice cube three rooms away.
2. “My ex used to…”
Anything that starts with “my ex” is one of those things to never say on a first date, full stop. I once spent twenty minutes comparing a dude’s hands to my ex’s hands. He texted me the next day: “hope you and your ex are very happy together.”
3. “I Googled you.”
Said it. Out loud. To a published author. He laughed… then blocked me.
4. “I’m actually not looking for anything serious.”
Cool, cool, cool—say this if you want them to sprint to the bathroom and climb out the window. Been there, watched it happen in real time at a taco joint in Queens.
5. “You look different from your photos.”
I swear this slipped out when the guy had clearly used 2016 filters. He replied, “Yeah, you look exactly like yours… unfortunately.” Burn unit, anyone?
The Ones That Haunt Me at 3 a.m. (More Things to Never Say on a First Date)
6. “Do you believe in soulmates? Because I think my cat is mine.”
Yes, I said this while showing not one, not two, but seventeen photos of Kevin (my tabby). Date ended with him “getting an urgent call from his roommate.”
7. “I’ve never really done this before.”
Lie. Huge lie. I’ve been on approximately 9,472 first dates since moving to NYC and yet I still pull this card when I’m nervous. It’s manipulative and weird—don’t do it.
8. “So… kids? How many do you want?”
Asked this on date #1 with a 28-year-old drummer. He looked like I’d asked him to donate a kidney on the spot.
9. “I’m between jobs right now.”
Translation: I got fired three months ago for crying in the supply closet and have been living off credit cards and spite. Somehow this never lands as charming.
10. “Wow, you’re so normal.”
I meant it as a compliment. It was not received as one.
Yeah So… Final Thoughts From Your Local Trainwreck
Look, I’m still single, still saying dumb shit, still learning the hard way that some things to never say on a first date will follow you like a curse. But also? Every single one of these disasters taught me something—even if it was just “order another drink and change the subject.”
If you take nothing else from my chaotic little heart, just remember: silence is better than word-vomit. (Though I’ll probably ignore my own advice next week.)
Anyway, tell me in the comments—what’s the worst thing YOU’VE ever said on a first date? Misery loves company and I’m basically a walking support group at this point.
P.S. If you see me at a bar in Brooklyn, please stage an intervention before I open my mouth.
(References for my dignity: some light reading on first date conversation tips from Psychology Today and why oversharing scares people off because apparently I need to outsource basic human skills now.)
