90 funny questions to ask a guy that will keep him laughing

Laughter is the bedrock of any successful relationship, which is why it’s great to have some funny questions to ask a guy in your back pocket. Not all funny questions work in all situations, which is why it’s best to have different ones depending on whether you want something weird, something cute, or even something deep.

In this article, we’ll offer you a few tips on asking funny questions and the best way to make people laugh, then we’ll take a look at several different types of funny questions to ask a guy you like.

Tips to make a guy laugh

Why is humor such a big deal in relationships? Well, for one thing, it can relieve tension and make awkward or uncomfortable situations easier. For another, studies have shown that humor is a key component of relationship satisfaction.¹ Here are some tips for the best way to use humor in your relationship, whether that’s through jokes or funny questions to ask a guy:

• Match the joke or question to your audience and the situation you’re in: Not all jokes or questions are appropriate for all situations, so think about where you are before potentially making things awkward or uncomfortable.
• It’s not funny if everyone’s not laughing: Some people, even with the best intentions, can accidentally cross a line from funny to cruel. If the target of your humor isn’t laughing, it’s not a joke.
• Don’t be afraid to be silly: The best humor comes from not taking yourself too seriously.

Weird funny questions to ask a guy

Normal is overrated. Here are ten weird funny questions to ask a guy:

1. If you could give a name to your favorite kitchen appliance, what would it be?
2. Is cereal a soup?
3. What is the weirdest combination of things you can buy at a grocery store?
4. If I were a [insert thing here], what would I be? Some suggestions: flowers, animals, or even celebrities.
5. Is ketchup a smoothie?
6. Would you rather speak in rhymes or with a different accent every day of your life?
7. If you had to turn into a food, which one would you choose?
8. If you had to dip something in mayo and eat it, what would you choose to eat?
9. If your favorite food could talk to you, what would it say?
10. What is better: a tiny scarf or a tiny hat?

Awkward funny questions to ask a guy

The best way to get over a moment of cringe is to laugh about it. This list of awkward funny questions to ask a guy will help you do just that.

1. Tell me about a time you did something stupid in front of your crush.
2. How often do you sing in the shower?
3. What’s the worst fashion mistake you’ve ever made?
4. What’s a world record that nobody would want to hold? What would make you willing to hold it?
5. Have you ever walked into a wall or a door? Why did you do it?
6. What’s the most embarrassing thing someone has ever walked in on you doing?
7. What’s one time I looked absolutely ridiculous?
8. What warning label would you put on me?
9. What’s the most useless gift you’ve ever received? Who was it from?
10. What’s the most socially unacceptable thing that makes you laugh?

Sometimes, funny questions can give you an insight into someone you didn’t know well before. Here are ten interesting funny questions to ask a guy you like:

1. If you could put any kind of clothes on a dog, what would you choose and why?
2. Would you rather be a vampire or a zombie? Why?
3. What animal would you say most describes your appearance? What about your personality?
4. If colors had scent, which one would smell the worst?
5. What’s the weirdest thing you believed growing up?
6. What’s the dumbest way you’ve ever injured yourself?
7. Which Disney character are you the most annoyed by?                                                                                                                                     
8. If you were a sandwich, what sandwich would you be?
9. What is the most ridiculous thing you’ve ever bought yourself? Would you but it again?
10. Would you rather have a giant dog, or a giant cat?

Funny deep questions to ask a guy

Just because a question makes you laugh doesn’t mean it can’t make you think. Here are ten funny deep questions to ask a guy.

1. What’s your favorite thing about me that nobody else will likely find cute?
2. If you were a sock, would you prefer to be worn on the right foot or the left?
3. Would you rather be super good looking with a low IQ, or the reverse?
4. When you were a kid, what did you think being an adult would be like?
5. Do you think you’re smart?
6. If you had a quest, what would it be?
7. What gift would you give your greatest enemy? Why?
8. If you could convince me to change my name to something else, what would it be?
9. What is your favorite conspiracy theory?
10. What conspiracy theory do you believe could actually be real?

Funny personal questions to ask a guy

Sometimes, humor is a good way to break the ice and get to know each other better. Here are ten funny personal questions to ask a guy:

1. What’s the most unbelievable thing about you?
2. Would you rather be nine feet tall or eleven inches tall?
3. Would you rather spend a week in a forest or a week in a real haunted house?
4. What’s the most original insult you can think of?
5. If you could only tell one joke for the rest of your life, what would it be?
6. Would you rather have pineapple on pizza or vegan steak?
7. Do people at work or in your social circle have a funny nickname for you?
8. What’s one app you really can’t imagine functioning without?
9. What’s the funniest dream you’ve ever had?
10. Name five songs you’d be embarrassed to admit you actually love.

Even if we’re all adults, there’s nothing wrong with being cute sometimes. Here are ten cute funny questions to ask a guy:

1. If your life was a TV show, what would the theme song be?
2. What makes you feel old right now?
3. If you could go to Mars but could never come back, would you go?
4. Would you rather eat only chocolate for the rest of your life, or fries?
5. Has there been any scene in a movie you watched as a kid that’s scarred you for life?
6. What board game can you not play in a civil manner?
7. What’s the most boring thing to do?
8. What cartoon character would you get along best with, and why? And get along worst with?
9. What’s the most useless talent you have, and how could it save the world?
10. Which fictional world would you NOT want to live in?

Flirty funny questions to ask a guy

Guys like funny girls for a reason. Here are ten flirty funny questions to ask a guy to show your interest:

1. What’s the funniest way you’ve had a date go wrong?
2. If we could compete in a reality show together, which one would you pick?
3. Would you ever go to a nude beach? Why or why not?
4. If you could have any fictional character play wingman/wingwoman, who would you pick?
5. What’s the most important file on your computer?
6. Would you rather forget your partner’s birthday or your anniversary every year?
7. What’s the cheesiest pick-up line you’ve ever tried?
8. What’s the cheesiest pick-up line you’ve ever had used on you? Did it work?
9. Would you rather marry the most attractive person or the best cook you’ve ever met?
10. Would you rather fight 100 duck-sized mes or one me-sized duck?

Funny sexual questions to ask a guy

Despite what romance novels may tell you, laughter only improves sex. Make the bedroom more fun with ten funny sexual questions to ask a guy:

1. What’s the silliest thing you’ve done to impress someone in bed? Did it work?
2. Would you ever try any of those Cosmo sex tips?
3. Have you ever been caught while you were in the middle of certain activities?
4. If you could have a one-night stand with any celebrity, who would it be?
5. Do you think food in bed makes sex better?
6. What would be the worst songs to put on a sex playlist?
7. Is it the weather, or is it just you who’s making me feel hot all over?
8. What’s the most out-there sexual thing you’ve ever heard of?
9. Which is better: goofy sex or rough sex?
10. What’s your go-to move if you were trying to impress someone… in bed?

Funny questions to ask a guy over text

Sometimes, it’s easier to have a conversation over text than it is face to face. So here is a list of ten funny questions to ask a guy over text:

1. What’s a meme that’s making you laugh right now?
2. What’s the funniest GIF you’ve ever seen?
3. Would you rather watch TV or movie bloopers, or funny videos of real people?
4. What’s the funniest thing, in your opinion, that you can buy on the internet?
5. How do you deal with people who mildly annoy you?
6. Would you rather be the class clown or the teacher’s pet?
7. What kinds of stuff makes you laugh the hardest?
8. What is something you find funny that absolutely nobody else you know does?
9. Would you rather be an unknown superhero or a famous villain?
10. Would you rather work alongside Dwight Schrute or Homer Simpson?

Funny questions are a seriously good way to strengthen a relationship

For most couples, asking each other funny questions is a great way to get to know each other better while still keeping things fun and light-hearted. Not to mention that having a list of funny and silly questions to ask a guy is a great resource for anyone who’s wondering how to move the conversation forward.

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