Questions To Ask A Guy To Get To Know Him Better

There are many ways that you can get to know a guy. Some are more obvious than others, but sometimes a more covert approach is the best route. Occasionally, you will have to take a roundabout approach in order to not startle someone, and that’s okay. It’s all about people skills and reading the room. Here is a list of questions to ask a guy to not only get to know him better but also bring him out of his shell.

  1. What’s your favorite song? If you’re big into music, you probably aren’t going to want to date a guy whose idea of hell is going to a concert or attending a festival. Music is a big part of life, and knowing what his tastes are — his favorite bands/singers, his all-time favorite albums, and his favorite song — will help you get to know this guy better.
  2. What’s one place you’d love to visit? Traveling has been challenging over the past several years, to say the least, but there has to be at least one city in the world he’s been dying to visit his whole life. Maybe he wants to go to that crazy robot restaurant in Tokyo or hike up Mt. Kilimanjaro in Tanzania. Encourage him to share — this could be an incredible conversation starter.
  3. What’s your favorite childhood memory? We all have certain childhood memories that stick out more than others. Ask him about the one that makes him feel all warm and fuzzy, that transports him back to being young and carefree and incredibly happy. This is one of the best questions to ask to get to know a guy as it gives you a window into who he once was that led him to become who he is today.
  4. What do you like to do for fun? You might know that he’s into watching sports and playing on his PlayStation, but maybe he also secretly likes building Lego models or learning languages. Getting an idea of his favorite pastimes can not only shine a light on who he is but could also potentially give you guys some great date ideas.
  5. If you could only eat one food for the rest of your life, what would it be? There has to be one, right? Could he legitimately live on pepperoni pizza forever? Would he be happy with an endless supply of french fries? No one doesn’t love talking about food.
  6. What’s more important in life: love or money? If he’s trying to date you, chances are he’ll probably say love just to keep the peace. However, try to be pragmatic here and encourage him to be honest. Whatever his answer is, ask why he feels that way and discuss. There’s no one right answer.
  7. What are you looking for in a relationship/partner? This isn’t just one of the best questions you can ask to get to know a guy better but also lets you know what you’re in for if you continue to date and eventually progress into a real relationship. What does he want or expect from a girlfriend? Is that aligned with your own desires? His answer here could be really illuminating.
  8. Who’s your celebrity crush? We all have one. It doesn’t matter how embarrassing it is. In fact, the more cringeworthy and strange his choice, the better. Of course, you’ll need to be prepared to open up about your own celeb crush as well, and prepare to be poked fun at if it’s someone really hilarious or unconventional.
  9. What are your feelings on PDA? Maybe he’s not into PDA and that’s cool because you’re not either. However, this is helpful to know if things get more serious between you. Does he want to hold hands when you’re out and about in the world? Would he prefer to keep any and all intimacy behind closed doors? Find out now so there’s less chance for awkwardness down the line.
  10. What’s something that not a lot of people know about you? He might not be ready to spill his deepest, darkest secrets at the moment, but asking a guy this question will help you get to know him in a way that not many other people do. Not to mention, it forms a basis of trust between you and lets him know it’s okay to be vulnerable, especially if you offer up a private tidbit of your own. Of course, both of you should only reveal what you’re comfortable sharing, but remember that it’s okay and even rewarding to be brave.
  11. What makes you happiest? What is it that really puts a smile on his face no matter how badly his day is going? Maybe it’s coming home to his dog slobbering all over his face. Maybe it’s going for a long run after a stressful week at work. Find out what it is that makes him feel good. You never know, you might feature on that list too, which is pretty sweet.
  12. Why did your last relationship end? Talking about exes doesn’t have to be awkward and in many ways, it’s kind of important. He doesn’t need to go into the nitty-gritty of exactly what went down with them, but a brief yet honest overview wouldn’t go amiss here. This tells you what his previous relationship challenges are and helps you understand what he might need work on or be sensitive about in the future.
  13. What’s the best gift you’ve ever received? He’s probably received plenty of presents over the years, but there are likely a few that really stand out as incredibly useful/sentimental/just really special. Ask him about it and try to recall some of the things you’ve gotten over the years that meant more than usual.
  14. What’s the thing you’re most proud of? Even if we’re not quite where we want to be in life right now, everyone has something to be proud of, no matter how small. Whether it’s being the first in his family to graduate college or the fact that he managed to finish a marathon, find out what accomplishment he really treasures and applaud him for it.
  15. Would you rather live in the city or the countryside? People generally have a preference when it comes to whether they prefer the bustle of a city or the quiet of the countryside. Is he into nature? Does he wish he could have a farm and live off the land? Or, does he prefer the loud, non-stop activity of a major city?
  16. Do you want to get married and have kids one day? This is one of the most basic yet most telling questions you can ask a guy to get to know him. After all, if he’s anti-marriage and plans on staying child-free forever and you’re ready to settle down ASAP (or vice versa), it’s better that you know now, even if the answer isn’t exactly what you hoped it might be.
  17. If you could have one superpower, what would it be? This is one of the sillier questions to ask a guy, but will still help you to get him know him. When he picks his preferred superpower, make sure you ask him why he chose it. Oh, and offer up your choice as well. Of course, invisibility and time travel are probably the best possible answers here, but he might come up with one that you’ve never thought of!
  18. What’s your favorite book? Does he read? If so, what’s his favorite book? You could even widen the scope here to ask who his favorite author is. His taste in literature will give you a lot of insight into who he is and what his tastes are. You might even discover that you have similar tastes in books and you can discuss. It’s like having your own personal book club.
  19. What’s your biggest fear? Whether or not we want to admit it, we’re all afraid of something. What’s something that freaks him out, whether or not it’s illogical or silly? Maybe he’s weirdly petrified of spiders, or perhaps it’s something deeper or more serious. This is a great question to ask when you want to get more vulnerable with him. Just be willing to share your fears as well.
  20. What is your biggest, wildest dream? Maybe you’re sitting on the floor of the kitchen at 2 a.m. texting and really tapping into something special. Why not unlock some of the big hitter questions? Don’t be afraid to put some important answers out there. Put your heart on the line. Tell your crush all about your hopes and dreams and the things you haven’t told anyone else about. You’ll find it’s easy to talk about hard things with people you trust.
  21. What’s your ultimate career goal? This might seem like it should come under the bracket of the previous point, but it really doesn’t. This is more logistical. Also, there are more ways to fail by this metric. If you ask questions about career goals, aspirations, or dissatisfactions, you will be entering an even more intimate realm. You can really discuss where you are in your professional life and where you’d like to end up, which can be empowering and encouraging.
  22. What’s your family like? Ask about his past. Did his parents get divorced or are they still together? Does he have any siblings? Did they do a lot of stuff together and were they really close-knit when he was growing up or is their relationship more distant? Discussing these things is a great way to bond over shared experiences and will also help you understand him more.
  23. What’s your friend group like? He’ll love talking about people he loves. Who are his closest friends and how long has he known them? Are they friends from school or more recent connections he’s made during his adult life? Do they hang out a lot or is it more of a “we don’t get to see each other much but when we do, it’s just like old times” type of vibe?
  24. What are your kinks? Why not get a sense of what interests them sexually. If nothing else, you can learn something new, or see if you’re compatible. You might laugh, but it does crop up in midnight conversations one way or another.

Coming up with interesting questions to ask a guy to get to know him in those early stages isn’t hard. After all, you’re just learning about each other so you’re basically starting from scratch and anything is game. You can use these questions as a jumping-off point, but be open to letting the conversation flow where it does naturally. You might be surprised by the insights you get.

Hannah has a Masters degree in Romantic and Victorian literature in Scotland and spends her spare time writing anything from essays to short fiction about the life and times of the frogs in her local pond! She loves musical theatre, football, anything with potatoes, and remains a firm believer that most of the problems in this world can be solved by dancing around the kitchen to ABBA. You can find her on Instagram at @_hannahvic.