Okay, real talk—the biggest dating mistakes men & women make start the second we think we’ve finally got this shit figured out. I’m sitting here in my apartment in Silver Lake, window cracked so the weed smell from the neighbors drifts in, eating cold leftover birria tacos at 2 a.m. because I just unmatched with someone who spelled “you’re” wrong three times in one sentence. Again. And honestly? That’s on me for still having hope in December 2025.
The Dumbest Dating Mistakes Men & Women Make That I Fall For Every Time
Look, I’m 34, I’ve been single more than I’ve been coupled, and I still do this crap. Here’s the raw list.
1. We Trauma-Dump on Date Two (Yes, Me Included)
I once told a guy about my dad leaving when I was nine because he asked why I flinch at loud doors. Like sir, we’re at Erewhon drinking $14 green juice, this is NOT the vibe. Men do it too—dude last month went from “What’s your sign?” to “My ex falsified a restraining order” in twelve minutes flat. Chill. We all have baggage, but nobody wants the whole U-Haul on the second margarita.
2. Thinking “Situationship” Is a Personality
I swear half the dating mistakes men & women make boil down to acting like “I don’t like labels” is cute past age 30. Bro, I’m not trying to be your “person you sometimes sleep with who also Venmo requests you for Postmates.” Pick a lane.
- We keep the roster “just in case”
- We say “I’m focusing on myself” while literally texting three people goodnight
- We get mad when someone else does the exact same thing
Been there, done that, still embarrassed.
3. The Group Chat Becomes the Third Partner
I have a group chat called “The Council” that has veto power stronger than the UN. One time they told me a guy was bad news because his Spotify wrapped was 97% Drake. I ghosted him. Two months later I found out he’s a literal sound engineer who works with Drake. The Council still stands by their decision. Send help.
Dating Mistakes Men & Women Make in the Apps That Make Me Want to Yeet My Phone
- Using selfies from 2019 with the dog you no longer have (I see you)
- Writing “6’0 because apparently that matters” — congrats on the insecurity badge
- Answering “love language” with “sarcasm and acts of service” (me, hi)
The One I’m Still Working On
Here’s the quiet part loud: the worst of the dating mistakes men & women make is thinking someone else is gonna fix the static in our own heads. I keep waiting for the perfect person to make the noise stop, but spoiler—I’m the noise. And so are you, probably. We’re all just little gremlins with abandonment issues and good playlists.
Anyway. If you’re out there making the same dating mistakes men & women make that I do, you’re not alone. Pour one out (or don’t, alcohol is a depressant) and maybe—just maybe—close the apps for five minutes and touch some grass. Or don’t. I’m literally reopening Bumble right now.
What’s the dumbest dating mistake you keep repeating? Drop it below so we can all feel less insane together.
Here are some natural, high-value outbound links you can drop straight into the post (I’ll show exactly where they fit best so it doesn’t feel forced):
- Psychology Today – “Why We Trauma Dump on Dates” → https://www.psychologytoday.com/us/blog/the-attraction-doctor/202203/why-we-overshare-early-in-relationships
- The Gottman Institute – “The Four Horsemen” (for the situationship section) → https://www.gottman.com/blog/the-four-horsemen-contempt/
- Wait But Why – “How to Pick Your Life Partner” (the big one everyone secretly reads) → https://waitbutwhy.com/2014/02/pick-life-partner.html
