40 Surprising Questions to Ask to Get to Know Someone 

I don’t know about you, but since the whole social distancing and lockdown thing, my already-lacking social skills have gotten worse. First, I’m still iffy about talking to people. Then, when I do, it’s almost like I don’t really know what to say. 

Unfortunately, many people feel their social skills are rusty in this semi-post-pandemic world. Maybe you find it difficult to strike up conversations with new people. Or when talking to someone face-to-face, you feel awkward, kind of like you’ve forgotten how to have a normal conversation.  

If you’re like me and not quite sure what to talk about with people, you probably turn to the obvious go-tos, like the weather, the latest TV show or something in the news. But those topics get stale fast. Plus, if you’re looking to meet new people or rekindle friendships that took a pause during the pandemic, this type of chitchat isn’t all that interesting. 

To push conversations forward and really get to know someone, experts say you’ve got to ask questions. And not just the basic ones. You’ve got to dig deep. “It’s important to go beyond the usual surface-level questions, because deeper questions help to build trust through vulnerability,” says Shontel Cargill, a licensed marriage and family therapist and regional clinic director at Thriveworks in Cumming, Georgia.  

In fact, one of the most famous studies about creating closeness, by psychologist Arthur Aron, Ph.D., found that two people who asked each other increasingly personal questions over a 45-minute period felt closer than two who only engaged in small talk during that time.  

So there’s your permission to get all up in someone’s business. Yes, it may feel weird, but you’ll probably find that many folks are quite receptive. “What we know, according to research, is people actually like and appreciate people who ask questions,” says Marisa G. Franco, Ph.D., a psychologist and author of Platonic: How the Science of Attachment Can Help You Make — and Keep — Friends. 

That said, read the room. If someone seems uncomfortable with your questions or only gives one-word answers, that’s your cue to fall back, Dr. Franco says. 

Another tip: If you ask, be willing to answer. 

These questions, gleaned from our experts, the Aron study and the book 4,000 Questions for Getting to Know Anyone and Everyone, by Barbara Ann Kipfer, can help you learn more about anybody — a relative, a new acquaintance, a friend, a date, even someone you’ve been seeing for ages. 

1. What’s on your travel bucket list and why? “These questions go beyond the surface level without being too personal, too soon, so they’re a good way to get to know people without overstepping boundaries,” says Cargill. 
2. What does true friendship mean to you? 
3. Who are you closest to in your family and why? 
4. What’s the weirdest thing you’ve taken a pic of with your phone? 
5. If you could do any other job, what would it be? 
6. What’s the most memorable compliment you’ve ever received? 
7. If you could have dinner with anyone in the world, who would you choose? 
8. What do you value most in friendships? 
9. What’s one dream you wish you could accomplish? “People tend to light up when talking about their beliefs, values and dreams, so asking questions along these lines can instantly build positive rapport and connection,” says Cargill. 
10. If you could have any talent, what would you choose? 
11. What’s one lesson life has taught you? 
12. You’re doing karaoke. What song are you singing? 
13. What are things people can do that make you feel valued or appreciated? 
14. Would you rather be the worst player on a good team or the best player on a bad one?  
15. What was your happiest moment in our friendship? “Talking about your friendship and reminiscing together can be powerful questions that create bonding,” says Dr. Franco. 
16. What’s something you read today that made you smile? 
17. If you could live to age 90 and keep either your 30-year-old mind or your 30-year-old body, which would you choose? 
18. What’s your idea of a “perfect” day? 
19. How do you define love? 
20. What’s your greatest fear? 
21. When was the last time you cried in front of someone? 
22. How do you like to receive support in times of need? Questions like this show you want to be there for that person, which can help build closeness, explains Dr. Franco. 
23. What mannerisms have you realized you got from your parents? 
24. If you had a crystal ball, what would you want to know? 
25. What are your needs in a relationship? 
26. What are some of your most fun moments in the past year?  
27. Is there any topic you feel should be off-limits for jokes? 
28. What do you miss most about being a kid? 
29. When someone walks past you, what grabs your attention first? 
30. What are some ways you’ve been working to develop yourself lately? 
31. Which would you rather spend, time or money? 
32. What’s your greatest accomplishment in life? 
33. What’s your relationship deal breaker?  
34. When was the last time you cracked up laughing? Why? Fun and laughter are good ways to build closeness and deepen a relationship, says Dr. Franco. 
35. How would you describe a perfect date night? 
36. What activity makes you feel alive? 
37. What are some experiences you’ve had that really affected the person you’ve become? 
38. What was your last random act of kindness? 
39. If you could, what moment in your life would you replay? 
40. What small thing makes you happy?