The 100 Company

Tuesday, June 30, 2026

What Conversation-Starting Questions Do You Ask on Dates?

Joanna Goddard

My dating posts are usually published on our newsletter Big Salad, so that first-date gossip and sex debriefs and breakup questions — as well as botox talk and therapist advice — can live safely behind a paywall (I don’t want my kids and neighbors to just stumble upon them!). But I love talking about dating and relationships here, too, of course, and am always eager to hear your thoughts.

So! The other day, one of my boys was heading out on a date (!), and he asked me what he should do if there were an awkward silence. “It’s okay to be quiet sometimes,” I reassured him. “But you can always have some back-up questions ready, if you want.”

I remembered a funny This American Life episode, where people shared loaded questions they ask on first dates. Editor Emanuele Berry asks potential partners what they think of Beyoncé, since “it’s a question that tells you how they feel about a powerful Black woman.” Another woman challenges her dinner dates to name their favorite Tom Hanks movies; she says the question serves as a low-stakes personality test. And Vivianne in Iowa says, “If your ex walked by right now with their new partner, what would you do?” which serves as a playful way of asking, how f-ed up was your last relationship?

On a goofier note, this McSweeney’s middle-of-the-date questionnaire made me laugh out loud. (#3. When the bartender came over, did you put on a little voice, or do you just talk like that?) (#37. Did I take too long in the bathroom, or was it weirdly quick?)

And when we watched Love on the Spectrum, Tanner, a 20-something in South Carolina, asked his date rapid-fire questions about animals: “Do you like lizards?” “Do you like snakes?” “Do you like tortoises?” “Do you like frogs?” “Do you like toads?” “Do you like sharks?” “Do you like jellyfish?” “Do you like octopi?” “Do you like squid?” “Do you like whales?” The sweetest.

On past first dates, I’ve liked asking about favorite movies, sibling birth order, and irrational fears — those topics often break the ice and lead to funny stories.

What about you? What questions do you ask on first dates? Any fun conversation starters? Or red-flag probes? And I’d love to hear: What dating advice do (or would) you give your kids?

P.S. My sister’s brilliant dating advice, five things that surprised me about divorce, and the sexiest podcast omggggg.

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