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. 

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. 

What does true friendship mean to you? 

Who are you closest to in your family and why? 

What’s the weirdest thing you’ve taken a pic of with your phone? 

If you could do any other job, what would it be? 

What’s the most memorable compliment you’ve ever received? 

If you could have dinner with anyone in the world, who would you choose? 

What do you value most in friendships?