The best conversation starters for people who hate small talk saved me last Thursday. I was on a Brooklyn rooftop. I wanted to jump into the East River rather than hear one more “Hot enough for ya?”
This girl I barely know walked up. She skipped hello. She asked, “What’s the worst advice you’ve ever gotten?” Ten minutes later we were crying laughing about our moms. Zero weather. Zero “What do you do?” I felt alive again.
So here’s my messy, very American list of questions that actually work.
Why Normal Conversation Starters Feel Like Torture
“What do you do?” is violence. My soul leaves my body. Last month at a baby shower I got trapped by a woman who said, “Hi, I’m a senior VP of synergy.” I wanted to vanish.
The Best Conversation Starters I’ve Tested on Actual Humans
These never flop. Even when I’m sweaty and over-caffeinated.
- “What’s something you believed way too long as a kid?” People lose it. One guy thought clouds were cotton candy until age 12. (There’s actually science on why kids believe wild stuff like this—here’s a quick read from The Atlantic.)
- “What useless skill are you weirdly proud of?” Mine: I can quote all of Shrek. Don’t @ me.
- “Ten-word Post-it to your 15-year-old self—what’s it say?” I answered this drunk in Denver and ugly-cried. Turns out this is basically therapy—there’s a whole Reddit thread that’ll wreck you.
- “What ridiculous hill will you die on?” Mine: pineapple belongs on pizza. Fight me. (BuzzFeed still has the definitive poll if you want ammo: pineapple pizza debate.)
- “When did you last feel like a kid again?” Someone said eating gas-station slushies at 30. Felt that in my bones.
Best Conversation Starters for When You’re Three Drinks Deep
Filter gone. Perfect time for chaos.
- “Petty thing you’ve never gotten over?” (Mine: ex said my laugh sounds like a hyena.)
- “If money didn’t exist, what would you do all day?” (Anyone who just says “travel” is lying—this study from Princeton backs me up.)
- “Song that makes you cry for no reason?” (“The Night We Met” wrecks me in Target parking lots.)
How I Stopped Sucking at Talking to People
Took me 32 years and roughly 400 Uber panic attacks. The secret? Care more about them being interesting than me looking cool. Mind-blowing, I know. (Celeste Headlee’s TED Talk on this literally changed my brain chemistry—watch it here.)
I carry a tiny notebook now. I steal every good question I hear. Zero shame.
When They Still Try the Weather Talk
Run. Fake a phone call. Chug water in the bathroom. Come back swinging with one of the big guns above. Works most of the time. The other times you just accept some people love surface-level and that’s… fine, I guess.
These best conversation starters for people who hate small talk legitimately changed my life. Or at least made networking bearable.
Try one tonight. Worst case: you learn a stranger’s weird secret. Best case: you make a new 2 a.m. existential-dread text buddy.
