The drinks are poured. The music is playing. Everyone has already talked about how crazy work has been lately. Now what?
Ask better questions.
We rounded up 58 of them, from the surprisingly revealing to the completely ridiculous. And because a good conversation, like a good cocktail, is all about balance, we built our list accordingly. A strong pour of Spirit, some tart Citrus, a little sweet Syrup, a few unexpected Mixers, and some easy Garnishes to top things off.
Pick one, ask the room, and see where things go.
Spirits: Questions that reveal a little soul.
Do you believe in ghosts?
If all salaries were the same, what career would you pursue?
What’s something you’ve changed your mind about recently?
What makes someone a good friend?
What’s something you care less about as you get older? And something you care more about?
How do you get yourself out of a rut?
What’s the best way to deliver bad news?
Who’s someone you’ve met recently that you immediately clicked with? Why?
If you could be the best in the world at one thing, what would it be?
What are you surprisingly good at?
If you had to move to a new city, where are you going?
What’s been inspiring you lately?
What’s something you’re sentimental about?
What’s something your younger self would be shocked to learn about you now?
Citrus / Sour: Questions with a little bite. You might pucker before answering.
What show do you pretend you’ve watched but haven’t?
What’s something everyone seems to love that you just don’t get?
What’s your most irrational pet peeve?
What’s the most overrated city you’ve visited?
What’s something you used to love that you now find embarrassing?
What’s something you knowingly overpaid for?
What’s something you pretend to understand but absolutely do not?
What’s something you judge people for even though you know you shouldn’t?
What’s something you’ve been putting off lately?
Syrup: Sweet questions. But not too sugary.
What’s a compliment you secretly love getting?
What’s a show you wish you could watch again for the first time?
What’s the nicest thing a stranger has ever done for you?
What smell instantly takes you somewhere else?
What meal reminds you most of home?
Who’s someone you wish you got to see more often?
What’s the best gift you’ve ever received?
What’s something you’re looking forward to right now?
What’s one place you’d happily return to every year for the rest of your life?
What’s a song you can’t hear without being transported to a specific time in your life?
What’s something completely ordinary that makes you disproportionately happy?
Mixers: The curveballs. Things get more interesting from here.
You get to pick a brand to sponsor you for the rest of your life. What is it?
You have $10,000 that you must spend frivolously by tomorrow. What are you buying?
What subject could you give a completely unprepared 20-minute presentation on?
What conspiracy theory do you wish were true?
If you had to open a restaurant tomorrow, what would you serve?
If your house had one completely unnecessary room, what would it be?
You can add one business within walking distance of your house. What are you putting there?
If you had to compete on a reality show, which one are you going on?
You can permanently eliminate one minor inconvenience from human existence. What goes?
If you had to become famous for something, what would you want it to be?
What would your extremely niche museum be dedicated to?
Garnishes: Little questions. Surprisingly revealing answers.
What’s on your algorithm lately?
What’s your room service order?
Who’s your celeb crush?
Window or aisle?
What’s your airport drink?
What’s always in your fridge?
What’s your diner order?
What’s your karaoke song?
What’s your gas-station snack?
What’s your Sunday-morning soundtrack?
What’s the oldest thing in your closet that you still wear?
What app do you open without even thinking?
What’s the last thing you bought that you love?
