151 Funny Questions to Ask a Guy Over Text & In Person

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Get to know him better with these fun and flirty questions

Co-authored by Laura Bilotta and Bailey Cho

Last Updated: November 15, 2024 Fact Checked

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Funny Questions

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Flirty

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Random

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Creative

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Personal

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Tips

Looking to make your crush or boyfriend laugh out loud? Asking silly questions is a great way to start an engaging conversation and learn more about him. In this article, we’re providing the ultimate list of funny and flirty questions to break the ice, whether you’re chatting in person or over text. We also talked to dating coach and matchmaker Laura Bilotta for tips on how to joke around with a guy!

Silly Questions to Ask Your Crush or Boyfriend

What gives you the ick?
What’s your biggest irrational fear?
What’s the worst movie you’ve ever seen?
What’s the funniest thing you believed in as a child?
What’s an embarrassing song that you secretly love?
If you could fight any historical figure, who would it be?
Would you rather talk like Yoda or breathe like Darth Vader?

Section 1 of 5:

Funny Questions to Ask Him

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Throw out a silly question to start a playful conversation. According to dating coach and matchmaker Laura Bilotta, “joking around with a guy can be a fun and lighthearted way to build rapport and show that you’re interested in getting to know him better.” Whether you’re talking to him in person or over text, asking a silly, unexpected question is guaranteed to get the giggles going:
- What gives you the ick?
- Is a hot dog a sandwich?
- What’s your favorite meme?
- What’s your most useless skill?
- What’s your biggest irrational fear?
- What was your favorite insult as a child?
- What’s the best prank you’ve ever pulled?
- What’s the worst movie you’ve ever seen?
- What's the grossest thing you did as a kid?
- What’s one fact you wish you could unlearn?
- What’s one thing everyone looks stupid doing?
- Would you rather be bald or have no eyebrows?
- Would you rather wear Crocs or Big Red Boots?
- Would you rather always shout or always whisper?
- What’s the most embarrassing thing in your closet?
- What’s the funniest thing you believed in as a child?
- If animals could talk, which one would be the rudest?
- If you could fight any historical figure, who would it be?
- What’s the worst text you’ve sent to the wrong person?
- What celebrity would be the worst leader of our country?
- What inanimate object would you delete from existence?
- What’s the silliest excuse you’ve given to get out of a date?
- What’s the weirdest thing you’ve seen in someone’s house?
- Would you rather talk like Yoda or breathe like Darth Vader?
- What’s an embarrassing song or band that you secretly love?
- How long do you think you would last in a zombie apocalypse?
- What’s the most savage insult you can come up with on the spot?
- What’s the most unnecessary white lie you’ve ever told someone?
- What’s the cringiest thing you’ve done to get someone’s attention?
- Would you rather always feel like you have to sneeze or sneeze 500 times a day?
- Would you rather talk like Donald Duck when you’re angry or turn into the Hulk when you’re turned on?
- Reader Poll: We asked 1167 wikiHow readers and 48% of them agreed that their favorite way to get to know someone is by asking funny or silly questions [Take Poll]. So, these wacky questions may help to improve your bond with this guy!

Section 2 of 5:

Flirty Questions to Ask Him

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Get his heart racing with these fun and flirty questions. If you’re trying to take your relationship to the next level, ask him some juicy questions to see if he likes you back. Find out his turn-ons, usual type, and relationship goals—it’s a great way to discover if you’d be a good match too!
- What’s your toxic trait?
- What’s your usual type?
- What’s your love language?
- What’s your biggest turn on?
- What song gets you in the mood?
- Do you prefer kissing or cuddling?
- When did you have your first kiss?
- What was your sexual awakening?
- Do you think you’re a good kisser?
- What song makes you think of me?
- Do you believe in love at first sight?
- What’s your biggest guilty pleasure?
- Have you ever gone skinny dipping?
- What’s your favorite thing about me?
- What’s your idea of the perfect date?
- What’s the most attractive body part?
- What was your first impression of me?
- When’s the last time you felt butterflies?
- What are your green flags in a relationship?
- What’s the most surprising thing about you?
- If you were me for a day, what would you do?
- What’s your favorite memory of the two of us?
- How do you know you’re really into someone?
- What’s the best pick-up line you’ve ever used?
- What’s the longest relationship you’ve ever had?
- If we had a Netflix show, what would it be called?
- Have you ever sent a dirty text to the wrong person?
- What’s the first thing you told your friends about me?
- Do you prefer being single or being in a relationship?
- If you could describe me in one word, what would it be?

Section 3 of 5:

Random Questions to Ask Him

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Ask about his personality and interests to get to know him better. If you’re not in the mood for a deep discussion, ask fun and random questions to pass the time. By expressing interest in his personal preferences and behavior, you show that you care about him and want to spend time together.^{[1]
X
Research source}
- Do you collect anything?
- Do you believe in aliens?
- What’s your spirit animal?
- Do you have any phobias?
- What’s your favorite scent?
- What’s your favorite season?
- What’s your dream vacation?
- What’s your biggest pet peeve?
- Do you have any hidden talents?
- What’s at the top of your wish list?
- Who was your first celebrity crush?
- What’s the theme song of your life?
- What could you write a book about?
- Are you a night owl or an early bird?
- What’s your favorite meal of the day?
- Do you prefer going out or staying in?
- What’s the greatest album of all time?
- Would you rather be too hot or too cold?
- Are you more introverted or extroverted?
- What’s the best concert you’ve attended?
- What’s the best gift you’ve ever received?
- Did you go through any phases as a teen?
- Do you believe in any conspiracy theories?
- What’s your unpopular opinion or hot take?
- Would you rather live without salt or sugar?
- Do you prefer watching movies or TV shows?
- Who would play you in a movie about your life?
- What bad habit would you break with hypnosis?
- Would you rather explore space or the deep sea?
- What’s something interesting you learned this week?

Section 4 of 5:

Creative Questions to Ask Him

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Suggest hypothetical scenarios to take the conversation to the next level. If you want to be unforgettable, ask a “what if” style question to catch him off guard and really pick his brain. It’s a great strategy to reveal more of his personality and prompt an engaging discussion!
- If you were invisible for a day, what would you do?
- If you were a mad scientist, what would you invent?
- If you could have any superpower, what would it be?
- If you could stop time for a year, what would you do?
- If you could change your name, what would you pick?
- If you could master one skill instantly, what would it be?
- If you could time travel, which decade are you going to?
- If you were president for a day, what would you change?
- If you woke up as an animal, what would you want to be?
- If you could play any instrument, what would you choose?
- If you won the lottery, what’s the first thing you would buy?
- If you could live in any fictional world, where are you going?
- If you could stay one age forever, which would you choose?
- If you could eliminate one historical event, what would it be?
- If the floor was lava, how would you get from place to place?
- If we hosted a comedy roast, what would you say about me?
- If you could make any kid’s TV show, what would it be about?
- If you could solve one problem in the world, what would it be?
- If you could only see one color, what color would you choose?
- If you could guest star on any TV show, what would you choose?
- If you were an Olympic athlete, what sport would you compete in?
- If you were given the death penalty, what would your last meal be?
- If we made up our own language, how would we greet each other?
- If you were born 100 years earlier, what would your occupation be?
- If you could master any language instantly, what would you choose?
- If you could only watch one movie for the rest of your life, what would it be?
- If you could only listen to one artist for the rest of your life, who would you pick?
- If you could create your dream band with 5 artists, dead or alive, who would be in it?
- If someone followed you around and narrated your life, who would you want it to be?
- If you could have an unlimited supply of one thing for the rest of your life, what would you choose?

Section 5 of 5:

Personal Questions to Ask Him

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Delve into deeper questions to see if you share similar values as him. Looking to deepen your connection with him? Touch on meaningful topics that move beyond the surface, such as his values, dreams, fears, and childhood.^{[2]
X
Research source} Asking personal questions is the best way to build trust and intimacy in a relationship, but if you’re worried about overstepping boundaries, preface by saying it’s okay not to respond if he feels uncomfortable.
- Who’s your hero?
- Are you religious?
- What’s your biggest fear?
- What keeps you up at night?
- What’s your idea of success?
- Are you close with your family?
- When’s the last time you cried?
- What are you most grateful for?
- What are you the most proud of?
- What’s your biggest regret so far?
- Do you believe in fate or free will?
- Is the glass half-full or half-empty?
- What’s your favorite way to unwind?
- What’s at the top of your bucket list?
- What was your dream job as a child?
- Do you care what people think of you?
- Where do you see yourself in 10 years?
- What’s your favorite childhood memory?
- Do you think money can buy happiness?
- How have you changed in the past year?
- What’s something you’re insecure about?
- What’s a little thing that makes you happy?
- What are 3 things you love about yourself?
- What role do you play in your friend group?
- What’s something no one knows about you?
- What’s the biggest misconception about you?
- Do you think physical or emotional pain is worse?
- What’s the best piece of advice you’ve ever received?
- What’s one thing you would do if you knew you wouldn’t fail?
- If your life was a book, what’s the title of the chapter you’re in right now?
Esther Perel, Psychotherapist

Ask each other questions. "When you learn something new about your partner—whether it’s funny and surprising or vulnerable and deep—you experience a stimulating contradiction: a meeting with the new and the comfort of recognition. Sharing new stories is a great way to evoke this."

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Tips

According to dating coach and matchmaker Laura Bilotta, “the best way to joke around with a guy is to be true to yourself.” Don’t try to force a joke or silly question if it doesn’t come naturally to you, and “focus on being authentic and playful in your interactions.”

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If you’re asking questions over text, dating coach and matchmaker Laura Bilotta recommends using emojis to “add a playful tone to your messages” and “help convey your sense of humor.” The 😉 (winking face) and 😏 (smirking face) emojis are some of the top flirty emojis to send your crush.

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