20 Interesting Questions to Ask a Guy


Last Updated: April 29, 2024

Sugar Baby

Looking for some interesting questions to ask a guy so that the conversation never hits a lull? Whether you’re trying to deepen your connection with someone you’ve been seeing for a while or convince your dream sugar daddy to take you on your first date, a fun Q&A session could be the ticket!

Time to get curious!

20 interesting questions to ask a guy

Round One: Icebreakers

These are great questions to ask when you’re just getting to know someone. If you’re looking for interesting questions to ask a guy who isn’t receptive to small talk, these should do the trick:

  • What’s the weirdest/most interesting thing that’s ever happened in your hometown?
  • If you could be CEO of your current company, what would you change? (And where would you take your first vacation?)
  • Do you have pets? If so, how spoiled are they on a scale of one to celebrity pets?
  • How would you describe your sense of style?
  • What’s one thing that people tend to get wrong about you?

As you can see, these questions are more creative takes on traditional small talk questions such as “What do you do for a living?” and “Where are you from?”

Round Two: Getting personal

These questions are meant to take your conversation a bit deeper:

  • What is the biggest thing you want to accomplish in life?
  • What is your love language? (Or, if you could make up your own, what would it be?)
  • What is something that you learned from your parents that you’re proud of?
  • What do you do when you have a problem with someone?
  • Do you have a hobby/opinion/fandom that you could talk about for hours on end?

These thoughtful questions can reveal a lot about a guy’s values, relationship with his family, and communication style. Make sure to take notes of the things he’s most passionate about and how he talks about his love language!

Round Three: Fun and silly questions

Fun and silly questions.jpg

Time to lighten the mood a bit with some lighter questions!

  • What is objectively the best breakfast food?
  • If it turns out that reincarnation is real, what or who do you think you were in a past life? Who or what would you want to be in the next?
  • What is the best band or musician of all time?
  • What is one thing in pop culture, technology, or today’s society that you think is way overrated?
  • What is something you’ve done as an adult that would totally shock your ten-year-old self?

Whether you agree about the best breakfast food or vehemently disagree about the best band, these questions are meant to spark lively, low-pressure conversations.

Round Four: Flirty questions

Ready to turn up the heat? This final round of flirty and interesting questions to ask a guy is sure to take your conversation to the next level!

  • Do you have any tattoos? Do you think I have any tattoos?
  • What’s the best gift that a romantic partner can give you? Feel free to interpret “gift” any way you want to!
  • What about my profile caught your eye?
  • What’s your MO for asking someone on a first date?
  • How do you know if you have chemistry with someone?

At this point, you should have a pretty good idea of what this guy is like, whether you’d like to see him in person, and if you have chemistry. That’s why these questions are intended to not-so-subtly turn the conversation towards you two moving things forward

Helpful tips on how to ask interesting questions to a guy


A good conversation is more than just asking questions. Here are a few ways that you can make sure this list of 20 questions works to spark a connection between you and your crush:

  • Consider your timing. If your guy just told you that he’s going into an important work meeting, it’s probably not the best time to pull out one of the more personal questions. And, you also don’t want to ask these 20 questions rapid-fire like an interrogation. Instead, you might bring up one or two of these questions when you guys are casually chatting at the end of the day or when you think the conversation could use a spark.
  • Think of the kind of relationship you’re pursuing. If, for instance, you’re looking for a fun fling, you’ll want to stick with questions that are light-hearted. If you’re talking to a sugar daddy, you may want to avoid questions about their immediate family or anything too personal. And for long-term relationships, you’ll want to focus more on what they’re looking for in a partner.
  • Don’t force an answer. These interesting questions to ask a guy are supposed to encourage enjoyable conversation. So, if he doesn’t want to answer something, don’t press the subject. Once you start to build trust, he may feel more comfortable opening up. But if you push too soon, he’ll put up his guard.
  • Be open to unexpected answers. One of the great things about the questions we’ve shared here is that they’re open-ended. You’re bound to learn some unexpected things about this person based on their answers, but remember to manage your own judgments and biases. You may not like or agree with every answer you get, but the point is to be curious and get to know the person on the other end of the chat!
  • Be ready to share your own answers. These early conversations are all about opening up and building rapport, so be ready to get vulnerable, yourself! Don’t ask any question that you’re not comfortable answering so that the back-and-forth feels balanced.
  • Let the conversation progress naturally. When you have good chemistry with someone, a simple question can flow into other topics and personal stories. This is a great sign! Don’t interrupt the flow by cutting in too abruptly with the next question on the list. Instead, let things progress naturally and only introduce the next question when the conversation hits a lull.

Which of these 20 interesting questions to ask a guy will you try?

Mix-n-match, ask them all, or come up with your very own questions. No matter what you choose, you’re ready to start chatting away with those guys in your DMs. Good luck and have fun!

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