Skip to Content

49 Funny Questions to Ask a Guy to Make Him Laugh

Setting the stage with laughter is a timeless social currency that can bridge gaps and build bonds — especially between romantic interests. When getting to know a guy or wanting to deepen an existing relationship, injecting humor is a great strategy. Asking funny questions helps you understand his sense of humor and shows off your playful side, making you more alluring.

The art of making someone laugh is not just about the punchline but also about timing and delivery. Knowing when to toss a playful quip or a hilariously intriguing question can make all the difference. It’s about reading the room and the person you’re engaging with. With the right questions at the right time, you can ignite bursts of laughter that make memorable moments.

Key Takeaways

  • A good laugh can significantly enhance your connections.
  • Your sense of humor highlights your personality and attracts others.
  • Timing is crucial for delivering funny questions effectively.

The magic of surprising: funny questions to ask a guy

What impression do you want to make? With these funny questions, you will get to know another side of the other person and make a difference. Surprise the other person with your originality.

funny questions to ask a guy to make him laugh - surprising

Being a fun person can be attractive and interesting. Besides, with these funny questions, you know where the conversation will start, but knowing where it will end is unpredictable.

  • What would be the first thing you would buy if you had unlimited money but could spend it only on things you didn’t need? 
  • If you had to tell your life story in a fictional book, would it be a comedy, a drama, or an encyclopedia?
  • If you were making a movie about your life and the cast were always people you have already met, who would you choose to play your role, and why? 
  • When you see a car head-on, do you associate the shape with a person’s face or a character? 
  • If you could be best friends with any historical figure today, who would it be, and what would you do?
  • What do you think blind people dream about?
  • Would you rather have a bit of laughter at a funeral or not be able to stop crying at your wedding?
  • If you had gone viral as a teenager, why would it have been? 
  • What is one truth about you that seems like a lie and one lie that could seem like the truth?
  • If you were a god and a holiday was held in your honor once a year, what kind of holiday would it be?
  • Would you like your pet to be able to talk, or would it reveal too many embarrassing things about you?
  • What is something that everyone knows but you find out much later in life?
  • What was your first fictional crush?
  • What would it be if you made an animal noise every time you sneezed?
  • What song or artist are you embarrassed to admit you like?
  • If you met your version 5 years ago, would you like him?
  • Would you prefer to be super nice and less intelligent or super bright but a little too rude?
  • What song would you play if you wanted to kick everyone out of a party?
  • Are you more into dad jokes or dark humor? What’s your favorite joke?
  • What’s the most cringe-worthy thing you’ve said or done this year?
  • What would you say if your house was robbed and you wanted to shout something random to scare the thief off?
  • What was your first fake name or email address on the internet?
  • How long have you had something expired in the fridge?
  • Do you usually imagine being in a video clip while listening to music while walking alone on the street? 
  • What death in a series or movie did you find the most absurd?
  • How do you feel more ridiculous? Running in flip-flops or with a backpack?

Tug of war: funny questions to ask a guy to make him laugh

It would help if you did not close yourself to questions for the conversation to flow. The idea is to carry on a naughty chat, using these funny questions as a comfort zone and a way to avoid awkward silences. 

funny questions to ask a guy - tug of war

On the other hand, while you must listen to what he has to say (and let him beat around the bush), you should also open up. Give your answer to the questions, and reveal another side of yourself.

  • If you had your religion, how would you be prayed to?
  • When was the last time you pretended to know the lyrics to a song?
  • What would it be if you could give men’s nipples a use?
  • What would your manual say if we all had a manual of use and warning instructions?
  • Would you rather use your favorite song as an alarm clock and end up hating it, or wake up every day to a song you already hate?
  • What odd combination of two products would you buy to make the cashier at the supermarket laugh? 
  • Have you ever had a time with emo bangs or ridiculous hairstyles? If yes, I demand a picture.
  • What would you do if you went back to when you were 10 but with your current knowledge? 
  • What weird hobby or habit would you discover if we moved in together?
  • What weird flavor combination is your guilty pleasure?
  • What would your stripper’s name be? 
  • What would be the reason you were fired on your first day of work? 
  • What would it be if you could have one use for your belly button?
  • How do you think deaf people imagine voices?
  • If every continent had a personality, what would it be?
  • What super embarrassing story from when you were little does your mother always tell?
  • If you were a superhero, what would be your weak point?
  • How would we have gotten along if we had met when we were 15?

Why do Guys Like Fun Girls?

When you’re playful and light-hearted, you display a magnetic sense of humor. Guys often appreciate a girl who can make them laugh because it indicates a shared sense of joy and capacity for fun in various situations. Imagine being on a first date, where nerves might be high; a funny quip or a witty observation can break the ice, making the date memorable and enjoyable.

Shared Humor in Relationships

  • Laughter as a Bond: It brings a sense of togetherness and can make you seem more attractive.
  • Ease of Connection: Your ability to joke about a “zombie apocalypse” or debate an absurd “conspiracy theory” makes conversations more engaging.
  • Relief Through Laughter: It acts as a stress reliever, creating a comfortable space for both of you.

Playful Challenges

  • Would you rather have a light-hearted game that can lead to hilarious scenarios?
  • Dare or Dare: Keeping it fun and not too serious can fuel a guy’s interest.
  • Prank Ideas: Sharing a laugh over harmless pranks hints at your adventurous side.

Being with someone who is considered “hot” isn’t solely about looks; it’s also about how someone makes you feel. If you can turn an ordinary moment into something more amusing—who wouldn’t find that attractive?

Having a superpower to be invisible might be a common fantasy, but the real magic lies in making each other visible through moments of genuine connection. Whether you’re discussing fight moves in a fictional zombie fight or laughing over who would be the last one standing in a fictional game, it all comes down to creating shared moments that fuel the connection. Humor is pivotal in strengthening ties, and having fun together keeps the relationship vibrant.

When to ask these questions

Finding the right moment to interject humor into a conversation with funny questions can turn a dull talk into an enjoyable experience. Consider the following scenarios where a light-hearted question might be the perfect touch:

  • Casual Get-Togethers: Being among friends is a comfortable setting to toss out a funny question. It can serve as an amusing conversation starter to keep the energy positive.
  • First Dates: Nervous? Break the ice with a laugh. Your date will appreciate the effort to keep things relaxed. “If you were an animal, which one would you be and why?” could elicit some giggles.
  • Long Drives: A road trip can sometimes hit a lull. That’s your cue to ask something absurd, like, “If you could have any celebrity as your GPS voice, who would it be?”
  • Waiting Times: Biding time in a queue or waiting room? A quirky question about a nickname or an odd joke can be just the ticket to a faster perception of time.
  • Post-Movie Discussions: Stir up a spirited chat with inquiries like, “If you had to live the life of a character from the last movie we watched, who would it be?”

Keep your questions upbeat and ensure they’re appropriate for the setting. You will know you’ve chosen well when you see the smiles around you. Remember, timing is key, and delivering your question with a friendly tone will likely get the best response.

Here’s a quick go-to list for moments that might welcome a touch of humor:

  • At a birthday party
  • On a coffee break
  • During a group hangout
  • While cooking together
  • After telling a joke to follow up on the laughter

You aim to add a spark to the conversation, not derail it. So watch for cues and choose your moment smartly to bring in that comic relief!

Funny questions to ask a guy to make him laugh: Let it flow

Remember, keeping the questions as light-hearted as a playful banter session is key. Bonding over shared laughs can be an effortless way to create memorable moments. So, next time you’re curious about someone’s favorite word or if they believe in karma from laughing at a ‘pull’ door, ask! After all, you never know what entertaining tales might unfold from such quirky inquiries.

If you’re willing to go one step further, here are some flirty “would you rather” questions to add some spice to your conversation. Have you ever asked someone one of these funny questions? How did it work? Tell us in the comments!