To me, small talk is purgatory. I feel a crushing sense of claustrophobia the moment I realize I’m locked in a dreary waltz of half-hearted comments about the weather or, god forbid, the differences between New York and Los Angeles. So, you’re more of a dog person? How compelling. Oh, the Uber from LAX took an hour? Wow, you should try stand-up comedy.

Now, I’m not just here to judge people who are bad conversationalists–it’s not their fault they are clinically boring. I am here to help people who find themselves nonconsensually trapped in empty conversation and want to figure out how to transition into “big talk,” or at least polite “medium talk.” As someone whose job requires that I interview people weekly, I’ve learned the art of asking relative strangers incredibly prying and personal questions. What I’ve discovered is that people are much more willing to engage in a topic of conversation if there is an element of novelty, personality, and surprise. Now, of course, don’t go all manic-pixie-dream-girl and start asking quirky questions to everyone you meet; instead, try some tactful ways to work an interesting topic into conversation.

Depending on your comfort level and confidence, I am offering 20+ icebreakers to move you out of the small talk zone and in a more compelling direction. No longer will you be caught in an endless loop of “Hey, how have you been?” and a cursory, “Good! How ‘bout you?” [Warning: I cannot guarantee these conversations will be pleasant–but they will certainly not be boring.]

  • What animal would you want to reincarnate as? How does this reflect the moral transgressions of your current life?
  • Do you think more people in the world are hot or smart?
  • Where did you get your outfit? If you died today, would you be happy with this ensemble as your ghost clothes for eternity?
  • Do you think flat earthers think the other planets are flat as well?
  • What superpower do you wish you had? How do you think the US government would weaponize it?
  • Did you know that Scarlett Johansson and Gisele Bundchen both have fraternal twins? How would you feel if you had a twin that was so much hotter and richer than you?
  • If you had to Freaky Friday with your mom or dad, who would it be and why?
  • Who is the ugliest celebrity you would have sex with?
  • How often do you think about Pangea?
  • Did you know woodpeckers can wrap their tongues around their skull, and that’s how they keep their brain from shaking when they peck? Do you think that feels as good as it sounds?
  • What does your sleep paralysis demon look like? Who would play them in a movie?
  • Did you know that, on average, the taller presidential candidate usually wins? What does America have against short people? Would Ron DeSantis be better off being short instead of wearing those boots?
  • Would you rather write the best novel ever written but no one could ever read it, or write a book you knew was awful but became an international bestseller?
  • Do you also have a crush on your therapist?
  • Would you rather wear all denim or all leather for the rest of your life? (underpants included)
  • Do you see yourself as more of a worm in a book or an owl in a graduation cap?
  • Do you have any secrets you’re saving to reveal on your deathbed?
  • What’s your favorite intrusive thought and why?
  • What’s the weirdest thing you can do with your tongue? (Keep it PG! Or at least PG-13)
  • What kind of religious trauma were you raised with?
  • Did you know part of the reason Napoleon lost Waterloo was because of his terrible hemorrhoids? Do you know how to spell hemorrhoids?
  • Would your biopic air on Lifetime, Discovery, TLC, or HBO?
  • Do you prefer dillying or dallying?
  • What would your catchphrase be if you were a Real Housewife, and how would you hold your object?

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