Running out of things to talk about can happen to anyone. Whether you’re hanging out with friends, texting your crush, spending time with family, or chatting with a coworker, having the right questions to ask someone when bored can instantly make the conversation more exciting.
The best conversations often begin with a simple question. Funny, deep, random, and thought-provoking questions help you discover new things about people while making even the most ordinary moments memorable. If you’re tired of awkward silence, this collection of 119 questions to ask someone when bored is exactly what you need.
Below are some of the best conversation starters to keep the discussion flowing.
“What’s the funniest thing that has happened to you this year?”
“If you could relive one day of your life, which day would you choose?”
“What’s something you’ve always wanted to learn but never started?”
“If money wasn’t an issue, what would you do every single day?”
“What’s your biggest irrational fear?”
“Which movie can you watch over and over without getting bored?”
“What’s the weirdest food combination you’ve ever tried?”
“If you could instantly become an expert at one skill, what would it be?”
“What’s your dream vacation destination?”
“Have you ever met someone famous?”
“What’s your favorite childhood memory?”
“If you had a time machine, would you visit the past or the future?”
“What’s one thing you wish everyone knew about you?”
“What’s the best compliment you’ve ever received?”
“If you had to eat one meal for the rest of your life, what would it be?”
“What’s the most spontaneous thing you’ve ever done?”
“Would you rather live by the beach or in the mountains?”
“What’s your guilty pleasure TV show?”
“What’s a hobby you’ve always wanted to try?”
“If you could switch lives with anyone for a day, who would it be?”
“What’s your favorite holiday and why?”
“What’s something that always makes you laugh?”
“If you won the lottery tomorrow, what’s the first thing you’d buy?”
“What’s your favorite way to spend a lazy weekend?”
“What’s one thing on your bucket list?”
“If animals could talk, which one would be the funniest?”
“What’s the best concert you’ve ever attended?”
“What’s your favorite season of the year?”
“Would you rather be able to fly or become invisible?”
“What’s your favorite board game or card game?”
“If you had an extra hour every day, how would you spend it?”
“What’s the strangest dream you’ve ever had?”
“What’s your favorite snack when you’re bored?”
“What’s something you’ve done that you’re really proud of?”
“If you could invent anything, what would it be?”
“What’s your favorite app on your phone?”
“Do you believe in luck or hard work?”
“What’s your favorite family tradition?”
“If you had your own TV show, what would it be about?”
“What’s the most beautiful place you’ve ever visited?”
“What’s something you’ve always wanted to ask me but never did?”
“If you could master any language overnight, which one would you choose?”
“What’s your favorite way to relax after a stressful day?”
“If you could only keep one social media app, which would it be?”
“What’s the best advice you’ve ever received?”
“What’s one thing people often misunderstand about you?”
“If you could travel anywhere this weekend, where would you go?”
“What’s your favorite thing to do on a rainy day?”
“What’s the most interesting fact you know?”
“If you could have dinner with any historical figure, who would it be?”
“What’s your favorite dessert of all time?”
“What’s one thing you’ve never tried but really want to?”
“If you could change one rule in the world, what would it be?”
“What’s the last thing that made you smile?”
“Would you rather explore outer space or the deep ocean?”
“What’s your favorite way to spend time with friends?”
“If you had a personal chef, what meal would you request first?”
“What’s your favorite smell?”
“If you could live in any fictional world, which one would you choose?”
“What’s something you’re grateful for today?”
“What’s your favorite animal and why?”
“If you could instantly solve one global problem, what would it be?”
“What’s the funniest joke you’ve ever heard?”
“Would you rather always be early or always be fashionably late?”
“What’s one thing you can talk about for hours?”
“If your life had a theme song, what would it be?”
“What’s your favorite thing about your hometown?”
“What’s the most adventurous thing you’ve ever eaten?”
“If you could bring back one fashion trend, what would it be?”
“What’s your favorite holiday tradition?”
“Would you rather never use your phone again or never watch TV again?”
“What’s one goal you’re currently working toward?”
“What’s your favorite quote?”
“If you could instantly read minds, would you?”
“What’s the kindest thing someone has ever done for you?”
“What’s your favorite outdoor activity?”
“If you had to describe yourself using only three words, what would they be?”
“What’s the most random thing you’ve ever bought?”
“If you could swap jobs with anyone for a week, whose job would you choose?”
“What’s your favorite ice cream flavor?”
“What’s something you’ve always been curious about?”
“If you could only listen to one music genre forever, which would it be?”
“What’s your favorite way to celebrate good news?”
“What’s the bravest thing you’ve ever done?”
“If you could have any animal as a pet, regardless of practicality, what would it be?”
“What’s your favorite thing to do before going to bed?”
“What’s one habit you’d like to improve?”
“If you could spend one year living abroad, where would you go?”
“What’s the most beautiful sunset you’ve ever seen?”
“What’s something you’ve accomplished that surprised even you?”
“Would you rather always have perfect weather or perfect Wi-Fi?”
“What’s your favorite childhood cartoon?”
“If you could make one wish come true today, what would you wish for?”
“What’s one thing that always cheers you up?”
“What’s your biggest dream for the future?”
“If you could rename yourself, what name would you pick?”
“What’s your favorite thing you’ve ever received as a gift?”
“What’s one challenge that made you stronger?”
“If you could ask your future self one question, what would it be?”
“What’s your favorite way to spend a completely free day?”
“What’s one memory that always makes you laugh?”
“If you could instantly become famous for something positive, what would it be?”
“What’s your favorite thing about the current season?”
“What’s one place you’ve never visited but know you’ll love?”
“If you had to give one life lesson to everyone, what would it be?”
“What’s the most unexpected compliment you’ve ever received?”
“What’s your favorite way to make someone smile?”
“If you could have unlimited supplies of one thing, what would you choose?”
“What’s something you’ve changed your mind about recently?”
“What’s your favorite tradition with your friends?”
“If you could create your own holiday, what would people celebrate?”
“What’s one thing that instantly improves your mood?”
“What’s your favorite memory from school?”
“If you could be remembered for one thing, what would it be?”
“What’s one question you wish people asked you more often?”
“What’s something you’ve never told many people?”
“If you could replay one conversation, which one would it be?”
“What’s your definition of a perfect day?”
“What’s one thing you’re looking forward to the most?”
