21 Questions To Ask A Guy To Get To Know Him Better

Whether you’re just getting to know each other or you’ve been together for months or even years, chances are there are parts of this guy that you still don’t know much about. There is always more to learn about a person, even someone you know better than anyone else. Here are 21 questions to ask a guy to get to know him better, spark meaningful conversation, and bring you closer together.

  1. If you could magically acquire a new skill, what would it be? Maybe he wants to speak a hundred languages or breath underwater. The reason behind his answer will be revealing.
  2. What music reminds you of your childhood? You may know a lot about the guy’s family and upbringing, but asking a specific question like this will give you deeper insight. You may even prompt a memory that he himself had forgotten.
  3. Did you have a childhood best friend? What was he/she like? This is another question that can conjure long-forgotten memories. Childhood friendships shape who we are as adults, even if they ended decades ago.
  4. Who is your dream dinner guest, living or dead? You can learn a lot about someone by knowing who these heroes are, especially when he has to explain what kinds of things he would want to talk to them about over dinner.
  5. What conspiracy theory do you think might be true? Hopefully, you’re not dating a full-fledged conspiracy theorist (unless you’re one too), but everyone has at least one historical event that they have lingering doubts about. Is it aliens? 9/11? Bigfoot? The answer is bound to start an interesting conversation.
  6. Who was your favorite childhood teacher? A lot of kids remember school unfavorably, but most of us were lucky enough to have one or two teachers who made a subject unexpectedly enjoyable or even changed the course of our lives. Who made his days at school easier and better?
  7. Have you ever stolen anything? Even the most law-abiding and risk-averse people have stolen something at least once in their life. Whether it was out of necessity or simply for the thrill of it, it’s bound to make a good story.
  8. Do you have any goals that you’ve had since you were young that you still want to achieve? Many childhood dreams become unfeasible or undesirable as we get older. However, some remain. Maybe he’s always wanted to be in a band or write a novel. Whatever the answer, you’ll learn something new about him.
  9. Have you ever gained anything positive from a lie? Everyone has lied. Some people hate admitting this. Even more difficult to admit, however, is a situation where you lied and got something good from it. You’ll find out how honest he is with this question.
  10. What was your first date ever? This will always lead to a good story. Was he one of those kids who had three girlfriends in preschool, or was he a late bloomer who never so much as held a girl’s hand until he was a senior in high school? How does his experience compare with yours?
  11. Do you think the world was a better place before social media? Is he an optimist about technology or a pessimist? Where do you stand? This is bound to spark a lively debate, even if you both know that at the end of the day, you’re too addicted to Instagram or Twitter to ever delete your accounts.
  12. What accomplishment are you most proud of? A lot of us are reluctant to admit being proud of something. It’s a vulnerable admission and tells you a lot about a person’s values. His answer may show you a new side to him. You may already know a long list of things he’s done in his life, but which one means the most to him?
  13. What is the worst date you’ve ever been on? If you’re looking for a good laugh, this question is always the right place to start. Hopefully, you’ll each have a few stories to share.
  14. What was the most pivotal decision you’ve ever made? This is one of the best questions to ask a guy to get to know him. Some decisions that seem trivial at the time end up being life-changing. Only in retrospect do we realize just what a big deal they were. He may surprise himself with the answer. How would you answer this question?
  15. Can you separate the art from the artist? Since the #MeToo movement, there have been many upsetting revelations about people who were once upheld as heroes. This has prompted the uncomfortable question of whether or not you can appreciate the art while knowing that the artist is a monster.
  16. Have you ever made a decision based on superstition? You may think he’s the most rational person you’ve ever met, but he’s bound to have a few crazy superstitions you never knew about. What are the weird superstitions he believes in even if he knows they’re BS?
  17. Where would you like to live if there were no obstacles? Maybe he has a secret desire to live in a rainforest or the heart of a city halfway around the world. Where would you choose to live? You never know, you might have a shared secret desire to buy a farm in the south of France or something. It’s possible!
  18. Have you ever seen a ghost? Even people who are adamant that there is no such thing as a paranormal world have seen something that they can’t explain.
  19. What would surprise your younger self most about your current self? This question will give you insight into who his younger self expected to be, and whether he feels he has surpassed his ambitions for himself or under-performed.
  20. If you weren’t in the line of work you are now, what profession would you have? Maybe he has a secret passion for marine biology or rock stardom. What would your answer be?
  21. How do you express love? This will give you some idea of whether or not the two of you are compatible. Do his ways of expressing love match with the way you like to receive love? If so, you might be right for each other.

Asking a guy these questions to get to know him will shed some more insight into who he is and will ultimately make you feel closer to him than you were before.

Rose Nolan is a writer and editor from Austin, TX who focuses on all things female and fabulous. She has a Bachelor of Arts in Theater from the University of Surrey and a Master's Degree in Law from the University of Law. She’s been writing professional since 2015 and, in addition to her work for Bolde, she’s also written for Ranker and Mashed. She's published articles on topics ranging from travel, higher education, women's lifestyle, law, food, celebrities, and more.