Fun Questions To Ask A Guy That He’ll Love To Answer

By now, you probably know that asking questions is the best way to get to know someone. However, it’s hard to know what to inquire about and what topics are better left off the table. If you need a few ideas in order to have an epic date night, here are some fun questions to ask a guy that he’ll love answering.

  1. What did you want to be when you grew up? He still might not know for sure, and that’s okay. Sometimes, our best career match happens later in life. This question is a lot of fun since it’ll remind him of his childhood in a positive way. Regardless of how or where he grew up, he still probably had dreams. It’s also interest interesting to compare what he wanted to do with what he’s currently doing now. Who knows? This question might even inspire him to go back to school or look for a better career match.
  2. What was the first concert you ever saw? It may be something silly, or it could have been an experience that changed his life. Going to a show for the first time can be overwhelming, so it’s often quite memorable. This can also start another conversation about music. You may end up learning the two of you have compatible tastes.
  3. What band would you love to see live today? If they’re still active and touring, this might be a good excuse to look up ticket information. Concerts make excellent dates. Plus, it’s always good to support your local music venues, especially after the COVID-19 pandemic.
  4. Who’s your favorite superhero? There’s a good chance he has one. It doesn’t even necessarily need to be someone from Marvel. It might be his mom, especially if he was raised in a single-parent household. It could also be a teacher or a sibling. There’s no wrong answer here.
  5. What’s your least favorite holiday song? The holidays always come around way too quickly. Inevitably, we all have to hear “Simply Having A Wonderful Christmastime” on repeat every December. This is a good question that might get him thinking. We all know which ones make us happy, but which song would he prefer to never hear again?
  6. What was the best gift you ever got? It could have been something he got at Christmas as a kid. Or, maybe a meaningful gift he received as an adult. This will help you get to know a lot about him and help you brainstorm other ideas for the future.
  7. When was your first kiss? Now remember, this question isn’t meant to start a fight. Your guy had a life before he met you. If you’re not the jealous type, this is a fun question to ask. There’s a good chance there’s a funny story behind it. Maybe he was in elementary school and he wasn’t expecting it. Or, maybe he was a late bloomer and had the whole thing planned.
  8. What are the ingredients for your ultimate sandwich? Nothing is off-limits here. Make sure he answers in full. Not only do you need to know about deli meats, but condiments as well.
  9. What gameshow will you never get tired of? Maybe he watches “Jeopardy!” every night but it’s never come into the conversation before. Or, perhaps he likes to watch late-night reruns of “Match Game PM.” He might not be into them now. Still, it’s amazing how gameshows are a big part of our memories. Which would he want to be a contestant on someday?
  10. What’s your favorite sketch from “Saturday Night Live”? The best part about “SNL” these days is that you can easily watch clips of the sketches on YouTube. The show still has a ton of wit after all of these years. But, it’s possible it was an older cast that he resonated with best. This conversation could also lead to a great night of pulling up sketches to share. This is one of the most fun questions you can ask a guy. Who wouldn’t love to talk about things that make them laugh?
  11. If you could only choose one fast food restaurant to eat at for the next year, what would it be? This question contains a lot of layers. You want to examine the overall menu and think hard about your choice. Once again, there’s no wrong answer for this one.
  12. What’s your favorite dish from your favorite restaurant? Maybe it’s something from his hometown, or maybe it’s local. When you find it out, the two of you can try recreating it at home if it’s too far to travel to. The way to a man’s heart is through his stomach, right?
  13. If you could live anywhere, where would it be? Don’t factor money in. Again, this question is rooted more in fantasy than reality. You can learn a lot about someone based on this question. For one, you can see if they’re more of a city person or country person.
  14. Have you ever cheated on a partner, why, and did they find out? This question is interesting on so many levels. It’s personal, but not too personal. And it allows him to respond with as much detail as he likes. The way he answers this will tell you whether he’s the kind of guy who thinks cheating is a big deal or not.
  15. Is there any game you were/are really good at playing? Maybe it’s a game he loved as a kid and kicked everyone’s ass at. Or, it could be a game that he dominates as an adult. If he’s the gamer type, he’s sure to love this question. It gives him a chance to brag about his skills.
  16. What’s your favorite/worst thing about yourself? Are you dating a super cocky guy, a man who displays a healthy dose of humility, or one who enjoys putting himself down? This question helps you find out while giving an idea of how he sees himself and how self-aware he is.
  17. Have you been caught having sex before? One time, I forgot to lock my doors and a guy I was seeing casually walked in on me and another guy in our birthday suits doing the nasty. It’s one of the most awkward experiences of my life but the story is hilarious every time I tell it. If he’s had an unfortunate moment like that, he might have fun sharing it with you.
  18. What’s your desert island movie or TV show? People love talking about their favorite things including that movie that they can never get tired of watching. I can talk for hours about how much I love Grey’s Anatomy or the American version of The Office. I’ve seen them dozens of times, to the point that I can narrate entire episodes word-for-word. This question is bound to have him rambling about his favorite film or TV obsessions.
  19. Ever been on a bad date? Almost everyone has a story about a date from hell. A date where nothing goes the way it’s supposed to and you just can’t wait for the night to be over. He’s going to have a lot of fun recounting his experience to you. And if you’ve both been on several terrible dates, you can trade stories back and forth until it hurts to laugh.
  20. What have you done that you’re most proud of? This will tell you what brings him fulfillment. You’ll learn what drives him and how he defines success and achievement. Once you can get him talking about his passions, it’ll be easy to drive the conversation towards other subjects.
  21. Is there a movie title that best explains your current life? The movie title to my life right now would probably be “I’m Thinking of Ending Things,” because I’m sick and tired of this pandemic and worrying about getting the virus. Whatever his answer is, it’ll give you an idea of the state his life is in at the moment and probably lead to a deeper conversation.
  22. What non-sexual thing turns you on? This is a slightly naughty question, but it’s not too dirty that it crosses a line, especially if you haven’t known each other for too long. It’ll give you an idea of the silly, out-of-the-box things that move him. This way, you’ll know how to get him fired up without taking the usual seduction route.
  23. What’s a great or useless talent that you have? Your guy may have hidden talents that will surprise you, but you might not learn about them until you ask. Maybe he plays the piano like Mozart or can contort his body into impossible shapes. Whatever amazing or silly skill he has, here’s your chance to find about it. And if you’re lucky, he might even put on a special talent show for you.

Asking a guy these fun questions will not only let you know more about him, it’ll give you plenty to talk about. Give it a try!

Karen Belz is a New Jersey native who is currently living in Maryland. She has a Bachelor’s Degree in Speech Communication with a focus in Broadcasting and Print Media Studies from Millersville University of Pennsylvania. Since graduating, she has written for sites like LittleThings, HelloGiggles, and Scary Mommy and is currently an e-commerce editor at Bustle.

When she's not writing, she enjoys making her phone run out of memory after taking too many photos of her dog. You can find her on Twitter @karenebelz or on Instagram @karenbelz.