100 Funny Questions to Liven Up Any Conversation

By | May 3, 2021
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Being a good conversationalist isn’t about waxing poetic on your own accomplishments, interesting as your life may be (sorry, pal). It’s about asking good questions and actively listening to the other person’s answers. Depending on the scenario, you might want to ask some deep questions that help you get to know someone better. Other times, you might to throw out some funny questions that break the ice or liven up the overall vibe of your hangout—which brings us to the list you’ll find below.

Whether you’re spending time with friends, talking to your crush, or on a date night with a long-term partner, these funny questions are sure to keep the good times rolling.

Funny questions about past experiences

  1. What’s your most embarrassing moment?
  2. Who was your first celebrity crush?
  3. Have you ever had a family vacation go horribly wrong?
  4. What’s the worst gift you’ve ever received?
  5. What’s the dumbest thing you ever did as a kid?
  6. What did you do for your birthday parties as a kid?
  7. What was your first job?
  8. What’s the stupidest way you’ve ever gotten hurt?
  9. What’s something totally ridiculous that you believed as a kid?
  10. What did you grow up believing about Santa Claus?
  11. What did you grow up believing about the tooth fairy?
  12. What did you grow up believing about the Easter bunny?
  13. What was your worst school field trip?
  14. Did you have to play an instrument in school?
  15. Did your parents ever give you an embarrassing haircut?
  16. What was your best Halloween costume?
  17. What was a movie you watched over and over again as a kid?
  18. When did you get drunk for the first time?
  19. Did you ever get detention in school, and what was it for?
  20. What’s the best prank you’ve ever pulled?
  21. What’s the worst meal you’ve ever made?
  22. Have you ever had a D.I.Y. project go wrong?
  23. Did your high school/college have any weird traditions?
  24. Who in your life has made you laugh the hardest?
    in bed and in love

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    Funny questions based on viral memes

    1. If a dog wore pants…
    2. Do you hear “yanny” or “laurel”?
    3. What colors do you see on this dress?
    4. What color is this Vans sneaker?
    5. Where are the middle girl’s legs?
    6. There are 12 black dots in this image. Can you see all of them at once?
      men sitting in urban roof garden laughing

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      Funny questions about famous people

      1. Which celebrity would you most want to be stranded with on a desert island?
      2. If we were forced to elect another celebrity to be the president, who would you pick?
      3. Which celebrity would you choose to be their VP?
      4. If you could have a one-night stand with any celebrity, who would it be?
      5. If you could marry any celebrity, who would it be?
      6. If you had to take a road trip with any celebrity, who would it be?
      7. If you could go for a beer with any celebrity, who would it be?
      8. If you could be famous for any skill in the world, what would you pick?
      9. Which actor would play you in a movie about your life?
      10. Which actors would play your parents in a movie about your life?
      11. If you had to tattoo a celebrity’s face on your body, whose would it be? (And where would you get the tattoo?)
        mature woman enjoying party at home

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        Funny questions about sex, love, dating, and relationships

        1. What’s the most awkward first date you’ve ever been on?
        2. What was your first kiss like?
        3. What was your first date like?
        4. Who was your first crush?
        5. Where’s the wackiest place you’ve ever hooked up with someone?
        6. Would you ever attempt to join the Mile High Club?
        7. Have you ever accidentally injured yourself during a hookup?
        8. If you and your crush had incompatible astrological signs, would you still want to date them?
        9. What do you think is the worst food you could possibly order on a first date?
        10. In your opinion, what’s a totally overrated sex position?
        11. In your opinion, what’s a totally underrated sex position?
        12. What would you do if you showed up to a highly-anticipated first date and realized you’d been catfished?
        13. Would you rather only be able to go on amazing first dates—and never see the people again—or be married to someone you’re only sort of attracted to?
        14. How did you first learn where babies come from?
        15. What’s the least helpful “birds and bees” talk you’ve ever received?
        16. What’s the most ridiculous myth about sex you’ve ever heard?
        17. What’s a completely non-sexual thing that turns you on?
          laughing friends hanging out together during backyard dinner party

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            Funny questions about hypothetical scenarios

            1. If you could only eat three foods for the rest of your life, what would they be?
            2. If you could only listen to one band for the rest of your life, what would it be?
            3. What’s your weapon of choice in a zombie apocalypse?
            4. How do you think you would fare in the Hunger Games?
            5. If you could be turned into a vampire—you’d live forever, but you’d have to subsist on blood and never see sunlight again—would you do it?
            6. If you could transform into any animal, what would it be?
            7. If you could only experience once season for the rest of your life, what would it be?
            8. If you could trade places with any Marvel or DC superhero, who would it be?
            9. If you had to fight any Marvel or DC villain, who would you have the best chance at defeating?
            10. What do you think you’d struggle with the most if you were cast on Survivor: the actual surviving part, or the strategy?
            11. If you could be a contestant on any reality show, what would it be?
            12. Would you rather have 10 enormous dogs or 100 pet snails?
            13. Would you ever volunteer to colonize Mars, knowing you’d never return to Earth again?
            14. If you found $ 1,000 cash on the ground, what would you do with it?
            15. You’re staying in a mountain cabin when a blizzard snows you in. Do you venture outside or hunker down for the long haul?
            16. If you had to live in any fictional universe, what would it be?
              young couple travelling by bus on rainy day having fun, london, uk

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              Funny questions about entertainment

              1. What’s the latest reality show you binge-watched?
              2. What’s the latest scripted show you binge-watched?
              3. What’s a game, TV show, or movie from childhood that you still enjoy today?
              4. What’s a TV show that people would be surprised to know you watch?
              5. What’s are the top three funniest movies you’ve ever seen?
              6. What’s a TV show that routinely makes you laugh out loud?
              7. Who’s your favorite stand-up comedian?
              8. When was the last time you laughed so hard you cried?
              9. What’s the funniest book you’ve ever read?
              10. Who’s your favorite funny author?
              11. What are you top three favorite movies that are so bad, they’re somehow good?
                happy men in a conversation

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                Funny “this or that” questions

                1. Would you rather sleep in pajamas or sleep naked?
                2. Do you prefer wearing underwear or going commando?
                3. Do you prefer to wash dishes immediately, or let them soak in the sink overnight?
                4. Would you rather have 10 enormous dogs or 100 pet snails?
                5. Eliminate one for the rest of your life: cake or ice cream
                6. Would you rather be a techno DJ or play in a live metal band?
                7. Eliminate one for the rest of your life: bottle service or boozy brunch
                8. Eliminate one for the rest of your life: cheese or masturbation
                9. Would you rather only be able to wear flip-flops for the rest of your life—no matter the occasion—or polished dress shoes?
                10. Would you rather only be able to wear a spandex bodysuit for the rest of your life—no matter the occasion—or a tuxedo?
                11. Would you rather go streaking or skinny-dipping?
                12. Would you rather get caught streaking or skinny-dipping?
                13. Would you rather have perpetual bad breath or B.O.?
                14. Would you rather have your parents catch you watching porn, or accidentally text your parents a nude?
                15. Would you rather have a permanent wedgie or socks that slide down your heels inside your shoes?
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