Typically, my dating posts get shared in our newsletter Big Salad, so that first-date tidbits, intimate details, and relationship quandaries — as well as botox discussions and therapist insights — stay securely behind a paywall (I prefer not to have my kids and neighbors accidentally encountering them!). Nonetheless, I enjoy discussing dating and relationships here too, naturally, and always welcome your input.
Just recently, one of my kids was going out on a date (!), and he wanted my advice on handling any uncomfortable silences. “It’s fine to have quiet moments,” I comforted him. “But, if you wish, you might prepare some fallback questions.”
I recalled an amusing episode of This American Life, where folks shared pointed questions for initial dates. Editor Emanuele Berry asks potential partners about their impression of Beyoncé since “it discloses their attitude toward a powerful Black woman.” Another woman prompts her dinner companions to name their top Tom Hanks films; she regards it as a harmless persona gauge. And Vivianne from Iowa asks, “If your ex strolled by right now with their new partner, how would you respond?” serving as a cheeky way to inquire about past relationship dynamics.
For a lighter touch, this McSweeney’s mid-date questionnaire cracked me up. (#3. When the bartender approached, did you use a different voice, or do you really talk like that?) (#37. Was my time in the bathroom excessively long, or strangely brief?)
Also, while watching Love on the Spectrum, Tanner, a young adult in South Carolina, rapidly inquired of his date 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?” So endearing.
In the past, on first dates, I’ve enjoyed asking about favorite films, sibling order, and irrational fears — these topics often lighten the mood and elicit entertaining anecdotes.
And you? What queries do you pose on initial dates? Any amusing conversation initiators? Or perhaps probing red-flag questions? Additionally, I’d be interested to know: What relationship advice do you offer (or would offer) your offspring?
P.S. My sister’s ingenious advice on dating, five revelations about divorce, and the most enticing podcast everrrrr.
