200+ Questions to Ask A Guy (Categories + Examples)

Carrying a conversation truly is an art, especially when you’re talking to someone new. If you can’t find the right topic to discuss, you might just find yourself looking at the other person in silence. Fortunately, this list of questions to ask a guy will help you spark that conversation, find common interests, and share experiences. 

You can use these silly, unique, and thought-provoking questions on friends, colleagues, or even your crush. If you’re trying to strike a conversation with a girl, we’ve got a list of questions to ask a girl, too! Feel free to use our question generator below to generate random questions:

Ice-Breakers

• Which late-night talk show host would you want to be stuck on a desert island with? 
• If you were invisible for an entire day, what would you do? 
• Which three people (living or dead) could you choose to have dinner with? 
• What is the most surprising thing about you? 
• Do you prefer cats or dogs? 

• If you could live in any time period, what would it be?
• How do you eat your pizza: folded, flat, or with a knife and fork?  
• What would the title of your autobiography be? 
• If you had the choice to live a day as any animal, which animal would you choose?
• What is the tallest building that you’ve ever been in? 
• Do you think you could survive a Zombie apocalypse? 
• Have you ever been to a Broadway show? 
• What are your two biggest pet peeves? 
• Which TV character can you relate to the most? 
• What is your most-used emoji? 

• If you could only listen to one musical instrument for the rest of your life, what would it be? 
• Are there any jokes that you have memorized for parties or to break the ice? 
• Do you have a celebrity doppleganger? 
• Who is your favorite Disney movie character? 
• What is your favorite dog breed? 

• It’s “Treat Yourself” day. What impulsive purchase are you making? 
• When was the last time you consulted Wikipedia for research? 
• What one book do you think that everyone should read? 
• If you could make one mythical creature real, which one would you choose? 
• What five travel destinations are on your bucket list?  
• Do you know your Myers-Briggs type? 
• If you could have one meal for the rest of your life, what would it be? 
• What three songs do you always queue up at a party? 
• Do you prefer to watch comedies or dramas? 

Silly Questions to Ask a Boy Friend

• Do you have any plans to get a tattoo? 
• What was the best prank you’ve ever pulled (or has been pulled on you)? 
• Do you prank people on April Fool’s Day? 
• How high over the speed limit do you typically go when you drive on the highways? 
• Have you ever made your own bread? 
• Do you know any songs in other languages? 
• How long would it take you to run a mile? 
• Do you prefer to wear bowties or ties? 

• What one invention do you wish you could take credit for? 
• Do you have a lucky shirt? 
• What movie remake should have never been made? 
• Have you ever written fan fiction? 
• Can you imitate any accents? 
• What is the weirdest thing that you have in your refrigerator? 
• Do you have any favorite adult cartoons? (Bob’s Burgers, Rick and Morty, etc.) 

• How often do you take bubble baths? 
• How long does it take you to come up with a Halloween costume? 
• Would you ever dress in drag? 
• Do you own an iron? 

• Have you ever worn a beret? 
• Do you enjoy completing puzzles? 

• Who is your favorite SNL cast member? 
• What is your skincare routine? 
• Have you ever taken dance lessons? Would you? 
• Do you have a library card? 
• If you were to go dumpster diving, where would you go? 
• What’s your favorite fun fact about history that no one knows? 
• At what age did you learn to make grilled cheese? 
• Have you ever watched a movie knowing going in that it was going to be terrible? 
• Do you like human names for pets?
• What’s the silliest Internet trend that you participated in? 
• Do you think that people should keep exotic animals as pets? 
• What’s a question that you like to ask people to get to know them? 

Questions About a Guy’s Interests and Hobbies

• What is the longest camping trip you’ve been on? 

• Have you ever stayed in a youth hostel?
• Which video game takes up the most amount of your time? 
• Have you ever driven a motorcycle? 
• Do you have a lock-picking kit? 
• Have you ever panned for gold?
• Are the sports you like to watch the same sports you like to play? 
• What was the first concert you went to? 
• Were you ever in Boy Scouts as a kid? What skills did you learn from it? 
• What’s your go-to karaoke song? 
• If your friends asked you to join a bowling team, would you? 
• Do you have a favorite visual artist? 
• What dish have you always wanted to learn how to make? 
• Which athlete is the true GOAT? 
• Do you like going to music festivals? 

• If you had a boat, what would you name it? 
• Where do you get your news? 
• If you could teach a class about one subject, what would it be? 
• What’s your most expensive hobby? 
• What TV game show do you think you’d win money on? 
• Do you prefer exercising by yourself or through group sports and activities? 
• Are fiction or non-fiction books more likely to keep your attention? 
• Would you rather go on Amazing Race or Survivor? 
• How do you entertain yourself on long road trips? 
• Do you think hunting is a fun hobby? 
• What was the last movie you saw in the theater? 
• Have you ever made a ship in a bottle? 
• How often do you work out at the gym? 

• If you were to go back to school, what would you study? 
• What is your favorite Quentin Tarantino movie? 
• Do you have a favorite author? 
• What DIY projects have you completed recently? 

Questions About Childhood and Family

• Do you have a good relationship with your parents? 
• Is there anything you believed as a child that blew your mind as an adult when you found out it wasn’t true? 
• What class do you wish you had taken in school? 
• Did you ever aspire to be an astronaut? 
• What was the first CD that you ever owned? 
• What’s the most money you’ve ever gotten from the tooth fairy? 

• How much of our childhood experiences impact who we become as an adult? 
• What was your favorite cartoon as a kid? 
• Do you like where you grew up?
• What is the cringiest haircut you’ve ever had?

• Do you still remember your favorite teacher? 
• Who was the last person you wrote a letter to? 
• What was your favorite activity at recess? 
• Who in your family do you try the hardest to impress? 
• What one day do you wish you could re-live from your childhood? 
• Who was the first person you had a crush on? 
• Did you ever have an imaginary friend?  

• What songs always remind you of your childhood? 
• Do you know your parents’ favorite movies? 
• What was your favorite video game as a child?
• Do you have any family heirlooms? 
• Which family member do you feel closest to? 
• Is there a question you’ve always wanted to ask your parents but haven’t? 
• What was your favorite subject in school as a child? 
• Did you dream about getting married as a child? 
• What is your favorite childhood memory? 

Questions to Ask Your Crush

• What is your favorite type of theme party? 
• Do you think any topics are taboo on a first date? 
• If you had a catchphrase, what would it be? 
• Are you friends with any of your exes? 

• What’s the best dating advice you’ve ever received from a friend? 
• Where are you most likely to listen to podcasts? 
• Do you like surprises? 
• Have you ever been on a brunch date? 
• Can you list five red flags that you look out for when meeting new friends or potential partners? 
• Are pet names cute or cringey? 
• How would your friends describe you? 
• What’s your go-to pick-up line? 
• Do you think that having a photo of a fish on your dating profile is “obligatory” or silly? 

• What’s an opinion that you hold that you’ve never wanted to share with your friends? 
• Do you know how your parents met? 
• What is your love language? 
• When is it okay to tell a lie? 
• Do you remember your dreams? 
• Can fighting be healthy for a relationship?
• What are your biggest deal-breakers? 
• Do you prefer the term “partner” or “girlfriend?” 
• How important is money to you in a relationship?
• Do you think that flirting is cheating? 

• Have you ever had a crush on someone at work? 
• If you had the chance to be the Bachelor, would you accept? 
• How do you handle rejection? 
• Are there things that are appropriate to not tell your partner? 
• Is there a specific age that you think you want to get married? 

Deep Questions to Start a Serious Conversation

• What’s your most vivid memory?
• If you had the choice to snap your fingers and eliminate the Internet altogether, would you? 

• What do you think happens after we die? 
• Have you made any plans for whether you want to be buried or requests you have for your funeral? 
• Who is the most influential person alive today? 
• What cultural norms would you like to see changed in the next few years? 
• How do you wish people would describe you?
• What crimes would you commit if you knew you would never get caught? 
• What are your top priorities in life? 
• What futuristic movie best depicts what our world is going to look like in 50 years? 
• What’s the most important lesson you learned from a terrible experience? 
• How do you turn your mood around when you’re feeling down? 
• If given the chance to know when or how you’re going to die, would you take that information? 
• What’s the best advice that you’ve ever received? 
• Do you believe in soulmates? 

• What are some signs that you should end a relationship (romantic or platonic) with someone? 
• Do you believe your life flashes before your eyes when you die? 
• When was the last time that you cried? 
• How do you know that you’re in love?
• What motivates you to get up in the morning?  
• If you could sit down with the five-year-old version of yourself, what would you tell them? 

Miscellaneous Questions to Ask a Guy

• What is one thing that you wish more women understood about men? 
• Do you separate your recyclables? 

• What’s a bad habit that you wish you could quit? 
• On a scale from 1-10, how tech-savvy are you? 
• Do you drink coffee in the mornings? If so, how do you take it? 
• If you’re just flipping through the TV, what channel are you most likely to land on? 
• Who is the most epic celebrity? 
• What is the next book on your “to read” list? 
• Do you pay attention to fashion trends? 
• If you could learn one language with the snap of your fingers, what would it be? 
• How much time do you spend on Reddit? 
• What are your favorite pizza toppings? 
• Which celebrity “villain” do you think is really a good person? 
• How many years will it take for humans to start living on the moon? 
• What are your favorite and least favorite household chores? 
• Can you remember the most expensive meal you’ve ever had? 
• What was the craziest bet you’ve ever made? 
• Who’s your favorite Muppet? 
• What was the last food that you tried and didn’t like? 
• Can you fall asleep on airplanes? 
• If you could have any painting in your home, what would you choose? 
• What’s the longest hiking trip you’ve been on? 
• When you see a spider, what do you do? 
• Plan your ideal vacation. What’s on the itinerary? 
• Who’s your favorite movie villain? 
• If you could change one thing about your job, what would you change? 
• Have you ever been to a Passover Seder? 
• Do you write in a journal? 

• What fashion trends do you wish people would stop? 
• Do you prefer to watch movies and TV shows with the captions on? 
• Does your car have a name?