13 Questions To Ask A Guy To Really Get To Know Him

When you’re getting to know a new guy, you want to move beyond small talk and really learn who he is. That might feel like an overwhelming task, but simple, friendly questions can actually reveal a lot. Here are some fun questions to get the conversations started.

  1. What do you like on your pizza? Silly? Sure. But food preferences tell a lot about a person. Is he a vegan who goes cheese-free? Does he pile on every tantalizing flavor possible? Is he strictly traditional? This is a low-key way to find out. Then go ahead and ask him to split a pie at your favorite pizzeria.
  2. What was the last movie (or book) that really surprised you and why? Life is more interesting with a guy who knows how to express his opinions on the arts. Playing critic will let you discover how he understands creative works. Does he zero in on tiny details? Go on and on about plot twists? Some of both? You can probably learn a lot about how he sees life by learning how he sees movies.
  3. What are your favorite guilty pleasure songs? Once you’re in a relationship, you don’t want to hide your love of hardcore metal or late ’90s boy bands. Get it out in the open now, then enjoy a judgment-free space where you both feel safe blasting your more embarrassing favorites. It’ll only bring you closer.
  4. What was your last big adventure? This question gives him an opportunity to impress you with tales of his wanderings. It also lets you see what he considers to be an adventure. Is his perfect journey a fancy European wine-tasting tour, or would he rather climb sheer rock faces? Either way, you’ll learn about him and a lot about your compatibility.
  5. What’s been the best day of your life so far? To know what makes him tick, you have to know what makes him happy. Was his perfect day quiet and calm or stuffed with spontaneity? Is he still holding on to a great memory from kindergarten, or did his best day happen recently? Most importantly, would you enjoy sharing similar experiences with him?
  6. What are your favorite traditions with your family? You definitely want to know what his family relationships are like, but you don’t want to come across like you’re grilling him. Knowing what moments he considers precious will tell you a lot without putting him on the defensive.
  7. Who are you closest to? Is it his big sister, his mentor, his best friend from third grade? Let him tell you about the bonds that mean the most to him and why. You might even pick up some good details to help you impress this person when he introduces you.
  8. Who do you really miss? Loss is a tricky thing to discuss, but you can gently open him up by keeping your questions general and receiving his answers without judgment. You might learn a lot about his family life, his past friendships and his grief process. And if he says he misses his ex, you can get out while you’re ahead.
  9. What about your life would surprise your younger self? Our grown selves don’t always match our childhood expectations, so this is a fun thought experiment. It also lets him tell you about his personal development over the years and his earliest ambitions. Who knows. Maybe you’ll even inspire him to revisit some of his abandoned goals and make his teenage self proud.
  10. What’s your biggest accomplishment so far? Humility is a good trait, but you also want to know that he’s got ambition and a sense of self-worth. And to understand what he values most. It shouldn’t be too hard to get him talking about his successes. He’s probably already looking for ways to impress you.
  11. What’s your hidden talent? Everybody likes to brag about their unusual skills now and then. Let him dazzle you with his lesser-known abilities. And even if it’s something ridiculous, give the guy a little ego boost and tell him he’s awesome. If you make him feel safe opening up, he’ll always want to share with you.
  12. What’s the most embarrassing thing you’ve ever done? After you’re done building up his ego, make sure he knows how to laugh at himself a little too. There’s no better way to bond than sharing cringey stories. And it will help you to see that even if this guy is truly incredible, he’s human just like the rest of us.
  13. What would you do if you won the lottery? It’s a classic fantasy for a reason. The idea of removing all obstacles to follow our bliss is totally imagination expanding. Let him share his dreams with you. You might even learn that he’s already on the path to his ideal life, windfall or no.
Jackie Dever is a freelance writer and editor in Southern California. When she's not working, she enjoys hiking, reading, and sampling craft beers.