My articles are usually featured in our newsletter Big Salad, which lets first‑date stories, relationship debriefs, and discussions on topics such as Botox or therapist advice remain behind a subscription barrier. This protects my personal network from accidental exposure while still inviting you to share reflections here.
The other day, one of my friends was preparing for a date and asked how to handle an awkward silence. I reassured him that pauses are natural, but having a few backup questions can keep the conversation flowing.
An excerpt from a This American Life episode reminded me of the power of loaded questions. One host asks potential partners what they think of Beyoncé, a question that can reveal their view of powerful Black women. Another asks dinner companions to name their favorite Tom Hanks film, serving as a low‑stakes personality gauge. Vivianne from Iowa poses the playful query, “If your ex walked by right now with their new partner, what would you do?” to gently probe past relationship baggage.
For a lighter touch, a McSweeney’s questionnaire sparked laughter. One item asks, “When the bartender arrived, did you adopt a different voice, or do you simply speak that way naturally?” Another reads, “Did I take too long in the bathroom, or was it oddly brief?”
During an episode of Love on the Spectrum, 20‑something Tanner from South Carolina fired off rapid‑fire animal‑related questions for his date: “Do you like lizards? Snakes? Tortoises? Frogs? Toads? Sharks? Jellyfish? Octopi? Squid? Whales?” The sheer earnestness was endearing.
On previous first dates, I have found that asking about favorite movies, sibling birth order, or irrational fears helps break the ice and sparks humorous anecdotes.
What about you? Which conversation starters have worked well on first dates? Do you have any amusing ice‑breakers or red‑flag questions you use? And what dating advice would you, or could you, give your children?
