151 questions to ask a guy they’ll actually like answering (2024)

Getting a conversation going can be tough—and if you’re looking for questions to ask a guy, don't fret over the specifics, gender doesn’t matter much: The more important factor is what are you trying to get out of the conversation. Looking for questions to ask your crush while texting? Trying to get a bit closer to your best friend? Just want to fill some awkward air time with your bestie’s sibling? Don’t worry, we’ve got questions for every single scenario.

Flirty Questions to Ask a Guy

What’s your love language?
Do you have a go-to pick-up line?
What’s your flirt style?
What do you find the most attractive about other people?
What’s your idea of the perfect date?
How do you know you really like someone?
Do you ever make the first move?
What song do you compare our relationship to?
If I were a flower, what kind of flower would I be?
Do you consider yourself romantic?
What does love mean to you?
When is the last time you felt butterflies?
What’s the worst pick-up line?
What’s the longest relationship you’ve ever had?
Do you have a type?
What do you most often think about before you fall asleep?
What puts you in a good mood?
What’s your ideal night in?
Do you like it when people flirt with you?
What would our first date look like?
Who was your first crush?
What makes you feel comfortable around a person?
What are you like as a boyfriend?
What’s your best relationship advice?
Would you rather give or receive a gift?
What’s the perfect way to ask someone out?
What’s your biggest dealbreaker when you’re on a date?
Do you believe in soul mates?
When are you going to ask me out?
What’s the most surprising thing about you?

Random Questions to Ask a Guy

What do you like most about me?
What would your chosen superpower be?
If you could be any insect, which one would you choose?
If you could only wear one colour for the rest of your life, which one would it be?
Are you a night owl or an early bird?
Do you often dream while you sleep?
How would you spend one million dollars?
What does your dream house look like?
If you could be a professional in any sport, which would you choose?
What are your favourite things to do on the weekend?
What’s your go-to joke?
What’s the funniest text you’ve ever gotten?
Do you have a favourite meme?
What movie makes you feel better whenever you watch it?
Are there any holiday traditions you wish your family practised?
If you could travel forward in time or backward in time, which would you choose?
You can attend a concert by any musician alive or dead—who do you choose and where is the concert?
If money weren’t an issue, what would your dream job be?
Sweaty or cold—which is worse?
Would you rather have a month-long staycation or a week-long adventure?
If you could trade places with any Marvel character, which one would you choose?
Ice cream every night for a month or the best pizza in the world every week for a year?
Sneakers or sandals?
If you could meet any one of your heroes, which one would you choose?
Would you rather write a bestselling book or paint a famous piece of artwork?
If you could plan the perfect day, what would be on the itinerary?
Group trips or solo trips?
Driver’s seat or passenger seat?
What’s a condiment that makes every food better?
What’s your picture-perfect breakfast?
Who would narrate a book about your life?

Personal Questions to Ask a Guy

What’s your biggest fear?
Where do you feel the safest?
What’s your favourite childhood memory?
Is there anything you would change about your childhood?
What did your childhood bedroom look like?
What’s the nicest thing anyone has ever done for you?
What do you see yourself doing in five years?
What’s the biggest life lesson you’ve learned so far?
Who is your biggest role model?
Have you ever read a book that changed your life?
What makes you feel the most confident?
Are you close to your parents?
Do you think you would be a good parent someday?
What’s your biggest regret?
Do you consider yourself an introvert or an extrovert?
What are you most thankful for?
What’s on your bucket list?
What are you most passionate about?
How do you hope people remember you?
What makes you emotional?
What’s been your highest point in life so far? What about the lowest?
What do you think your best quality is?
What is one thing you would change about yourself?
Have you ever lost someone close to you?
Are you good at giving advice?
Are you a spiritual person?
What isn’t real that you desperately wish was?
What’s the biggest lie you’ve ever told?
What’s the biggest compliment someone have ever given you?
Which is more important: love or money?

Funny Questions to Ask a Guy

If you could switch bodies with the president or your favourite actor, which would you choose?
If you could be an airplane or a train, which would you choose?
What’s the worst text you’ve accidentally sent?
Who is your favourite comedian?
Is cereal soup?
Is a hot dog a sandwich?
What kind of secret society would you start?
What’s the most embarrassing thing in your closet?
What inanimate object would you delete from existence?
What’s the funniest nickname you’ve ever been given?
What would be the worst “buy one, get one” sale item of all time?
What would three of your cheat codes be if life was a video game?
Do you know anyone who reminds you of a cartoon character?
What’s the best inside joke you’ve ever been a part of?
If all animals could talk, which one do you think would be the rudest? How about the funniest?
Would you rather sneeze or fart loudly every hour?
What do you think the best WiFi name is?
Do you judge people for putting pineapple on pizza?
What’s the most useless invention of all time?
Which instrument do you find the most annoying?
What’s the most obnoxious colour?
What’s an invisible thing you wish humans could see?
What’s the weirdest thing you’ve ever smelled?
What movie would be much better as a musical?
What’s one thing everyone looks stupid doing?
What three items would you buy together at a grocery store to make a cashier laugh?
What’s the best type of cheese?
What’s the oddest thing you’ve seen in someone else’s home?
What’s the funniest insult you can come up with on the spot?
What mythical creature do you wish was real?

Questions to Ask a Guy Over Text

How was your day?
Do you have a favourite genre of movies?
If you could listen to any song on repeat for a week straight, which would you choose?
Would you rather be a rock star or a movie star?
If you had three wishes, what would they be?
Do you have a go-to recipe?
Do you prefer cats or dogs?
What are you thinking about right now?
What’s something you’ve done recently that you’re really proud of?
How would your best friend describe you?
What’s the weirdest thing that’s happening to you this week?
What was the best vacation you’ve ever taken?
What emoji makes you think of me?
What would be on a playlist you make for me?
How would you describe yourself in three words?
How would you describe me in three words?
What’s your favourite Wikipedia page?
What do your weekends look like, and how do I fit into them?
How do you describe me to your friends?
What unnecessary products do you deem necessary to your life?
Guess what emoji I put next to your name right now on my phone?
What’s the most useless advice you’ve ever gotten?
What’s something you’ve always wanted to ask me?
Would you ever stay friends with an ex?
What are your five most frequently used emojis?
Do you prefer texts or calls?
What do you wish you had more time for?
What would you make me for dinner?
What kind of conversations do you enjoy the most?
When do you feel the happiest?