Questions to Ask a Guy to Get to Know Him Better

Starting a Relationship

By: Milena J. Wisniewska

They say dating isn’t an interview, but it kind of is.  

If you spend more time selecting nail polish than choosing a boyfriend, don’t be surprised that you end up the victim of a walking red flag. 

I’m not saying you should interrogate the fella like a murder suspect, but having some creative questions tucked in your back pocket can potentially save you a few months of therapy.

Table of Contents:

Questions to Ask a Guy to Get to Know Him Better

  • What’s your favorite way to spend a weekend?
  • What are your hobbies or interests?
  • Do you like to travel? If so, where’s the best place you’ve visited?
  • What’s one thing you’re passionate about?
  • What’s the most fascinating thing you’ve learned recently?
  • Are you more of an early bird or a night owl?
  • What’s your favorite way to relax after a long day?

You’re looking for questions that will help determine your overall compatibility. According to a study published in PNAS, “A core theme in relationship science is that compatibility is essential — that most relationships succeed or fail because two people fit well or poorly together.”[1]

For example, if your ideal weekend involves the gym, a swim, and an early morning hike, while he’s partying until four a.m., you might be better off as friends. 

According to a survey by the Pew Research Center, 45% of adults believe that having shared interests is very important for a successful relationship.[2]

According to a survey by the Pew Research Center, 45% of adults believe that having shared interests is very important for a successful relationship.

Learn about who he is. See if you are compatible and, in the process, you’ll appear interesting and likable. 

It’s true! Researchers conducting a study published in the Journal of Personality and Social Psychology found that asking a question and then two follow-up questions dramatically increases how likable others perceive you to be.[3]

Sure, asking questions is key, but it’s equally important to match questions to the depth of your connection.

Early on, focus on his life experiences, values, and dreams instead of jumping into childhood traumas right off the bat.

Deep Questions to Ask a Guy 

  • What’s your biggest dream or aspiration?
  • What’s your favorite way to practice self-care?
  • What’s the most meaningful compliment you’ve ever received?
  • How do you handle disagreements or conflicts in a relationship?
  • What’s your favorite quote or mantra?
  • How do you define trust in a relationship?
  • What are your beliefs and values regarding sexual intimacy, and how do you see them fitting into our relationship?
  • Are there any unmet needs or desires you have in our sexual relationship?
  • What are your top three values in life?
  • Do you want to get married and/or have children someday?

Say, the lucky guy made it through the first date. Kudos to him! 

In this section, I simply must mention Dr. Arthur Aron’s 1997 study, which asked 36 questions about how to help people fall in love. It went viral thanks to Mandy Len Catron’s 2015 New York Times essay series “To Fall in Love With Anyone, Do This,” where she shared her own love-struck experience using questions that start profound and end up Mariana Trench deep.[4

Time to channel your inner Leo from Inception and dive into his mind with some revealing questions.

Let’s see if he can handle your wit and charm while you unearth his innermost thoughts, fears, and hopes. 

Because, let’s face it, nothing says romance like a bit of intellectual spelunking!

If it doesn’t feel like his depth matches your pool, it’s usually a sign you’re not an intellectual match.   

Flirty Questions to Ask a Guy

  • What do you find most attractive about me?
  • What’s your love language? 
  • Do you consider yourself romantic?
  • Do you like it when a girl makes the first move?
  • Do you have any go-to flirting techniques or moves?
  • What’s your biggest turn-on?

Once you know you’re compatible and your values align, you have my blessing to introduce some flirty fun. 

Unleash your edge with some spicy questions that’ll plant some tantalizing ideas in his mind. But watch out, things might get steamy . . .

Of course, keep it within your comfort zone. 

These questions are meant to create sexual tension but burn slowly. Unless you want it to burn fast. You go, girl!  

The great thing about subtle flirting is that it’s pretty low stakes with a massive potential payoff. 

Researchers Gersick and Kurzban report in Evolutionary Psychology that flirting “conveys the signaler’s intentions and desirability to the intended receiver while minimizing the costs that would accompany an overt courtship attempt.”[5]

Asking him some flirty questions is an easy way to let him know you’re into him. 

Random Questions to Ask a Guy

  • If you could live in any era, which one would you choose?
  • Who’s your favorite fictional character?
  • What’s your guilty pleasure?
  • What’s the most spontaneous thing you’ve ever done?
  • What’s the most interesting fact you know?
  • If you had to describe yourself in three words, what would they be?
  • What’s your go-to karaoke song?
  • If you could visit any fictional world, where would you go?

You’ve nailed hobbies, values, dreams, and sparks. Now it’s time to go over your quirks. See if he can handle your unique brand of weird. 

Serve him your unique mix of hilarious and thought-provoking questions to keep him on his toes and get the conversation going. 

Personal Questions to Ask a Guy

  • What’s your favorite childhood memory?
  • How do you typically spend your weekends?
  • Who has been the most influential person in your life?
  • What’s something you wish people knew about you?
  • How do you maintain relationships with your family and friends?
  • What’s a goal you’re currently working towards?
  • What’s the best advice you’ve ever received?
  • How do you handle conflict in your personal life?
  • What’s a hobby or interest you have that people might find surprising?

Once you’ve gotten to know each other and your connection has leveled up from “strangers on a train” to “partners in crime,” it’s time to dive into some more profound stuff. 

I’m talking about questions that peel back the layers of his life, like an ogre, or an onion — family, friends, childhood traumas, and personal growth.

These questions should create a vibe of intimacy and trust without making him feel like he’s under FBI interrogation. 

Think of it as exploring his soft, gooey center. Handle with care!

By asking personal questions like these, you’ll learn what he’s passionate about. Remember to ask follow-up questions!

Interesting Questions to Ask a Guy

  • What’s the best book you’ve ever read and why?
  • If you could master any skill instantly, what would it be?
  • What’s your favorite travel destination and why?
  • What’s one thing you think everyone should experience in their lifetime?
  • How do you stay motivated and inspired?
  • What’s your favorite way to unwind after a long day?
  • If you could have dinner with any historical figure, who would it be and why?
  • What’s a cause you’re passionate about?
  • What’s your favorite way to express creativity?
  • If you could change one thing about the world, what would it be?

This guy seems like a catch, but what if he has some conspiracy theories on the shape of our planet or drops Andrew Tate quotes when cornered by other males? 

While you’re digging for critical intel on his compatibility, don’t just stick to the basics. Explore his travel adventures and unique life perspectives. Ultimately, you want to know if, beyond a soft, cuddly marshmallow, he can hold his own in a conversation with your dad. 

Weird Questions to Ask a Guy 

  • If animals could talk, which one would be the rudest?
  • If you could only eat one food for the rest of your life, what would it be?
  • What’s the most bizarre talent you have?
  • If you could have any fictional creature as a pet, what would it be?
  • What’s the strangest compliment you’ve ever received?
  • What’s the best sandwich?

Catch him off guard! 

Ask unusual, off-beat questions that can lead to hilarious or unexpected responses. After all, in the words of Dr. Seuss,

“We are all a little weird, and life’s a little weird, and when we find someone whose weirdness is compatible with ours, we join up with them and fall in mutual weirdness and call it love.” 

We’re all serious people, but that doesn’t mean we need to BE serious. 

See how he handles your weirdness and how far his weirdness goes.

With these weird and funny questions, you’ll get to know his quirky side.

Fun Questions to Ask a Guy 

  • If you could be a character in any movie, who would you be?
  • What’s the funniest thing that has ever happened to you?
  • What’s your favorite board game or card game?
  • If you could live in any sitcom, which one would it be?
  • What’s the most ridiculous thing you’ve ever bought?
  • If you could create a holiday, what would it be called and how would it be celebrated?

Whether you’ve been an item for 10 days, 10 months, or a decade, staying clued in on each other’s quirks and preferences is key to keeping things fresh and fun. 

And I’m talking about asking him whether he’d still love you if you were a pickle. 

Think playful questions that keep the vibes light and the laughter flowing. Perfect for breaking the ice after a tiff or just keeping the good times rolling.


Naturally, any of these questions can be asked at any point in your romantic journey. 

You decide, based on your vibe, how far you’d like to take it and when. These are just some suggestions to make sure you don’t end up with someone who’s inherently wrong for you.

Mix up your questions to keep things interesting. Throw in some deep stuff to see if he’s got a soul, some flirty banter to check if he’s got game, and a dash of random weirdness to test if he can handle your quirky side. 

Remember, though, it’s not just about the questions — it’s mainly about the answers. Listen to what he says and see if it aligns with your dreams and values. 

Approach these chats with a mix of curiosity, humor, and openness, and you’ll be better equipped to dodge the Tamlins and find your High Lords of the Night Court.😍

Check out our page to read more about getting into a relationship.


What are the best questions to ask a guy to get to know him?

The best questions to ask a guy to get to know him depend on your intentions and the stage of the relationship. Early on, it’s helpful to ask open-ended questions about his interests, hobbies, and background to get to know each other. Later, more personal and reflective questions can foster a deeper connection, such as “What do you value most in a partner?” or “What did you learn from your past relationships?” 

How can I tell if a guy likes me based on the questions he asks?

You can tell if a guy likes you based on the questions he asks, which reflect his level of interest and intentions. He may ask personal questions to get to know you better, like your hobbies, family, or future plans. He might show concern for your well-being and ask about your day or feelings. Questions about your interests and opinions indicate he values what you think. 

What to ask a guy on chat?

What to ask a guy on a chat depends on your level of familiarity and the purpose of the conversation. If you’re just getting to know each other, ask about his hobbies, interests, or favorite movies. For flirting, you might ask about his ideal date or what he finds attractive in a person. If you’re discussing shared interests, dive deeper into those topics with specific questions.


1. Baxter, A., Maxwell, J. A., Bales, K. L., & Eastwick, P. W. (2022). Initial impressions of compatibility and mate value predict later dating and romantic interest. Psychological and Cognitive Sciences, 119(45).

2. Smith, A., & Anderson, M. (2018, March 1). Social media use in 2018. Pew Research Center.

3. Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn’t hurt to ask: Question-asking increases liking. Journal of Personality and Social Psychology, 113(3), 430–452.

4. Catron, M. L. (2015, January 9). To fall in love with anyone, do this. The New York Times.

5. Gersick, A., & Kurzban, R. (2014). Covert sexual signaling: Human flirtation and implications for other social species. Evolutionary Psychology, 12(3), 549–569.


  • Milena J. Wisniewska

    Milena might not be a relationship professor, but she's definitely been through it all, learned her lessons, and is here to spill the tea. She combines the wisdom of renowned relationship specialists with her own romantic adventures to offer relatable and practical advice.

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