Questions to ask someone that aren’t small talk

Aug 7

Here are some engaging, thoughtful, and unexpected questions you can ask at singles events (or anywhere you're trying to actually get to know someone beyond small talk):

✨ Personal & Reflective

What’s something you're currently working on?
What’s a piece of advice that’s really stuck with you?
What’s something you’ve done that you’re really proud of?
What chapter of your life are you in right now?
What’s something you’re learning about yourself lately?
What’s something you're trying to unlearn?
What does a “good day” look like for you right now?
What’s a boundary you've learned to set that changed everything?
What’s a value you try to live by, even when it’s hard?
What's something small that instantly improves your mood?

🧠 Thoughtful & Unexpected

What’s a random skill you’d love to master, just for fun?
If you could live a totally different life for one year, what would it look like?
What would be the title of your current life chapter?
If you had to teach a class on anything non-academic, what would it be?
What’s something you believe that most people would disagree with?
Would you rather time travel to the past or the future—and why?
What’s something you wish more people asked you about?
If your younger self could see you now, what do you think they’d say?
What’s one belief you’ve changed your mind about in the past few years?
What’s a risk you’re glad you took?
When do you feel most like yourself?

💬 Emotionally Intelligent

What kind of support feels most meaningful to you?
What’s something you’re currently working on — internally?
How do you usually recharge when you’re burnt out?
What makes you feel truly seen in a conversation?
Is there a compliment you’ve never forgotten?

🌍 Perspective-Based

What’s something you think is underrated in life?
What’s a life lesson you keep learning over and over?
What’s something that shaped you, but you rarely talk about?
What’s your personal definition of “success”?
What do you think people misunderstand about you?

📚 Pop Culture & Nostalgia

What’s a trend from your teen years that you fully embraced?
What album or artist always brings you back to a specific time in life?
What fictional universe would you most want to live in for a day?
What’s a book, movie, or song that changed the way you see the world?

💬 Relationship-Oriented

What’s something you appreciate in a friendship or relationship?
What’s one green flag you’ve learned to look for?
What’s a dealbreaker that’s totally fair—but oddly specific?
Who’s a couple (famous or not) you admire and why?
What’s a love language you’ve grown to appreciate more over time?
What’s a relationship lesson you learned the hard way?
How do you usually show people you care about them?
What kind of energy do you bring to a first date?
What’s something people get wrong about dating you?

🔮 Imaginative / Future-Forward

If someone gave you $50,000 to spend only on experiences, what would you do?
What’s a dream you haven’t pursued yet?
What would your ideal Sunday look like 5 years from now?
What’s something you’ve done and was glad you tried?
What’s one dream you’ll never give up on, even if it takes years?
What’s your “if I won the lottery, I’d do this tomorrow” plan?
Where would you go if you could disappear for one week, no responsibilities?
If your future self wrote you a letter, what do you think it would say?
What’s a dream that feels just out of reach — but still possible?
What kind of life do you imagine yourself living 10 years from now?
If money, time, or fear weren’t a factor — what would you start tomorrow?
What’s one thing you hope never changes about you?
What version of you are you trying to become?

Want to get practice asking these questions in real life? Join us for a singles event in your city.

Bo Turner