175 Conversation-Starters to Entertain You and Your Friends

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IN THIS ARTICLE

1 What If?

2 Getting Deep

3 Pop-Culture

4 Music

5 Hobbies

6 Favorite Memories

7 Embarrassing Moments

8 Things That Scare You

9 Astrology

10 Fashion

11 Sports

12 Travel & Nature

13 Goals & Future

14 Deepest Secrets

15 Love

16 Personal Beliefs

17 Food & Drinks

18 Social Media Posts

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Co-authored by Allison Broennimann, PhD and Danielle Blinka, MA, MPA

Last Updated: April 12, 2024 Fact Checked

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We’ve all been there—sitting in awkward silence, or staring at a blinking cursor. Even if you think you already know everything about your friends, we’ve dug up some interesting topics to discuss. We’re here to help you chat with your bestie, get to know your friends better, or connect with a new acquaintance. Whether you're hanging out or texting, we’ve compiled 175 fun, quirky, and deep questions you can ask your friends about a slew of entertaining topics.

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1

What If?

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   Imagining weird scenarios is fun, especially with friends. A simple question can turn into a long, interesting chat—and maybe some inside jokes. Take turns suggesting a wacky “what if” scenario, then figure out how you’d each react. You might find yourself in a deep discussion about space travel or zombies.

   • Where would you go if you had a time machine?
   • What would you buy if you won the lottery?
   • Where would you go on a dream vacation?
   • What would you do if you saw a ghost?
   • Who would you have dinner with if you could dine with anyone?
   • What would you do if you woke up with magical powers?
   • If you could go into space, would you take the trip?
   • What would you do if vampires were real?
   • What pet would you get if you could have any animal?
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2

Getting Deep

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   Have fun with your friends by asking thought-provoking questions. Get to know your besties better! With these prompts, you'll make each other laugh and reveal your silliest secrets. As you guys start to get serious, show your friends that you care by holding eye contact, nodding your head, and just being an awesome, active listener.

   • How would you describe me in 3 words?
   • What actor would play you in a movie?
   • What are your biggest pet peeves?
   • What cheers you up most when you’re having a bad day?
   • What’s your favorite meme or gif?
   • Would you rather be a dog or a cat?
   • What’s the most random fact you know?
   • What nickname would you give me?
   • If you were a dessert, what would you be?
   • What’s your guilty pleasure?

3

Pop-Culture

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   Connect over fandoms by discussing movies, TV, books, or podcasts. Pop-culture is a great go-to for people you’ve just met and old friends. You can give each other recommendations, or debate your pop-culture opinions. You could also talk about your favorites and why you like them best.

   • What book moved you the most?
   • Which TV show, book, or movie would you want to be your life, and why?
   • Which is better: Chilling Adventures of Sabrina or Charmed?
   • Which superhero should get their own movie next?
   • Which is better: DC or Marvel?
   • Which character would you want to cosplay?
   • Which podcast do you listen to the most, and why?
   • Which movie would you like to see made into a TV series?
   • Which creature do you like better in movies or TV: vampires, zombies, werewolves, witches, or mermaids?
   • Have you ever watched a movie that was better than the book?
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4

Music

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   Chat about your favorite artists and jams with friends or someone new. While you likely share some favorites, you could have some interesting differences. Chat about the artists who’ve changed your life, and have fun talking about your musical dreams.

   • Which artist’s music impacted your life the most?
   • What songs would you put on the soundtrack of your life?
   • What song could you listen to on repeat?
   • Which instrument would you want to play?
   • What would you want to call your own rock band?
   • Who do you hope to see in concert soon?
   • Who was the first artist you saw in concert?
   • What song do you wish your favorite artist would cover?
   • What song would you pick at karaoke?
   • What song do you think I should sing at karaoke?

5

Hobbies

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   Your hobbies and interests are a gold mine for conversation. Plus, hobbies can be a lifesaver when you’re chatting with someone you just met. You can talk about your similarities or differences, depending on what you’re feeling that day. Add personal details or ask a follow-up question to keep your chat alive.

   • What do you do in your free time?
   • How do you express your creativity?
   • Do you have any hidden talents?
   • What hobby have you always wanted to try?
   • What do you collect?
   • What’s your favorite thing to do when you’re alone?
   • What’s your favorite game?
   • What do you like to do on weekends?
   • Do you prefer to go to the movies or a coffee shop?
   • What’s a new interest you’ve discovered?
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6

Favorite Memories

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   Entertain each other for hours with personal stories. You and your friends will find it easy to talk about your experiences, so you'll quickly find something to say. Plus, you’ll probably become closer friends. After they open up, compare stories or share something similar that happened to you.

   • What’s your most cherished memory?
   • What memory haunts you?
   • What’s your favorite memory of us?
   • What memory do you wish you could forget?
   • What’s your favorite memory from your birthday?
   • What’s your favorite holiday memory?
   • What’s your first memory?
   • What did you do over summer when you were young?
   • What’s your best memory with your grandparents?
   • What memory makes you laugh the most?

7

Embarrassing Moments

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   Your biggest embarrassments usually make hilarious stories. There’s no one better to tell those stories to than your besties. They’ll listen to your most embarrassing secrets and laugh along with you, not at you. Your squad won’t be able to stop laughing at the mishaps your past selves overcame.

   • What’s the most embarrassing thing that ever happened to you?
   • What would embarrass you the most?
   • What do you think was my most embarrassing moment?
   • What’s the most embarrassing event you’ve witnessed?
   • How do you deal with embarrassment?
   • Have you ever stopped going somewhere because of something embarrassing?
   • What’s more embarrassing: tripping down the steps or getting toilet paper stuck on your shoe?
   • Has anyone ever laughed at you?
   • What is the most embarrassing thing in your search history?
   • What’s an embarrassing misunderstanding that you’ve had?
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8

Things That Scare You

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   We all have fears, and they’re often super interesting. From nightmares to phobias, there’s a lot to unpack here. When you’re talking to your closest friends, your fears might be the perfect topic to discuss. To keep the convo going, ask follow-up questions. For instance, if they tell you what they’re afraid of, ask them how long they’ve had their fear.

   • What’s your biggest fear?
   • What’s the scariest nightmare you’ve had?
   • What fear do you wish you could conquer?
   • Which is scarier: clowns, snakes, or spiders?
   • Would you stay in a haunted house? Why or why not?
   • What have you avoided because of fear?
   • In what ways has fear motivated you?
   • What’s the scariest story you’ve ever heard?
   • Do you like scary things?
   • Are you afraid of getting old?

9

Astrology

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   Let the stars guide you to a chat about astrology. Your friends (and new acquaintances) likely all have opinions about their zodiac signs. Plus, astrology is fun and interesting to discuss! You might compliment their sign’s strengths or talk about what makes you compatible as friends.

   • What’s your sign?
   • What’s your moon sign?
   • Do you believe in astrology?
   • What sign would you never date?
   • Do you think another sign fits you better? Which one?
   • Do you feel like the moon affects your behavior?
   • Have you ever bought gift items labeled with your sign?
   • Do you read your horoscope?
   • Would you ever base your plans on what your horoscope says?
   • Do you think my sign fits my personality?
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10

Fashion

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   What you choose to wear can tell people a lot about you. Fashion is a way to express yourself, so you actually learn about each other when you talk about it. Share your favorite styles, your biggest fashion moments, or your worst fashion disasters. You might just come up with some new looks.

   • How would you describe your style?
   • What’s your most regrettable fashion moment?
   • Do you like shopping in-person or online?
   • What’s your favorite piece of clothing?
   • What’s your must-have accessory?
   • Who is your fashion inspiration?
   • Do you prefer sweats or fancy outfits?
   • What three words summarize your fashion sense?
   • What fashion era do you love the most?
   • What character has the coolest fashion?

11

Sports

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   You can talk about sports with practically anyone. You might talk about what you play if you’re an athlete, or you could discuss your favorite sports or teams. If you and your friend support the same team, try watching a game together so you can chat about what happens.

   • What sports do you play?
   • What are your favorite teams?
   • What sport do you wish you could play?
   • Have you ever been to a professional sporting event?
   • Are you watching the game that’s on?
   • What’s your best achievement from a game?
   • Which athletic skill would you like to improve most?
   • What Olympic sport do you wish you could try?
   • What snack do you always get at the ballpark?
   • Have you ever scored a winning point?
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12

Travel & Nature

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   There’s so much out there in the world to explore. Plus, this is an easy topic for any friend, even if you’ve just met. Find out where people have gone and where they’d like to visit. It’ll be fun getting everyone’s opinions, and you might even learn something new about a place you haven’t visited yet.

   • What’s the best vacation you’ve ever had?
   • Where would you go if you could go anywhere?
   • What are your travel essentials?
   • What’s better: the beach, the mountains, or the city?
   • Do you prefer to relax on vacation or to explore?
   • What city do you think is the most romantic?
   • Would you have a vacation fling?
   • Would you rather go on a cruise or to a ski resort?
   • Do you prefer flying or going on a road trip?
   • What cultures would you like to experience?

13

Goals & Future

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   Chances are, you and your friends daydream about the future. Share those dreams with each other so you can help make them come true. Getting encouragement from your friends can actually help you reach your goals. Plus, it’ll help strengthen your friendships.

   • What do you think is your greatest accomplishment?
   • What are 3 things that are on your bucket list?
   • What’s your biggest goal right now?
   • What makes you the most nervous about the future?
   • What’s your dream job?
   • What quality would you like to have as an old person?
   • Where do you see yourself in 5 years?
   • What does your dream house look like?
   • Who do you wish could mentor you?
   • What does success mean to you?
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14

Deepest Secrets

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   Your besties are the perfect people to share your secrets with. They shouldn’t judge you, so you can really get things off your chest. Open up and get to know each other on a deeper level.

   • What’s your favorite thing about being you?
   • Have you ever done something you really regret?
   • What’s something you’ve never told anyone?
   • What’s your silliest habit?
   • What’s something you wish you could change?
   • What reality show do you wish you were on?
   • When do you feel lonely?
   • What have you cried about recently?
   • What’s one thing you wish you could change about yourself?
   • What’s a lie you’ve told?

15

Love

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   Swapping dating advice can be a great way to bond with your pals. You can totally talk about love with your friends, and you might get really great insights from their experiences. Even if you’ve never been in love, you’ve probably thought about it, so you’ll have something to say. If they share something heartfelt, let them know that you appreciate their honesty—because this can make your friend feel safe and deepen your connection.

   • What was your worst first date?
   • Have you ever been in love?
   • How many times have you been in love?
   • What’s your love language?
   • Do you believe in soul mates?
   • How old do you want to be when you fall in love?
   • Do you think people can love more than one person at the same time?
   • Is falling in love a priority for you?
   • Do you believe in love at first sight?
   • Do you think marriage is important?
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16

Personal Beliefs

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   It’s fun to have thought-provoking conversations with your friends. Create a safe space by agreeing ahead of time that it’s okay to agree to disagree if a conflict pops up. Just focus on learning something interesting and getting to know each other better.

   • What cause is most important to you?
   • What changes should we make to help the environment?
   • What social justice issues are your passion?
   • Do you consider yourself religious or spiritual?
   • What is something you used to believe but have changed your mind about?
   • Do you think some acts are unforgivable?
   • What’s an important life lesson that you’ve learned?
   • Do you believe in miracles?
   • What topics make you most uncomfortable?
   • How would you define your political beliefs?

17

Food & Drinks

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   We eat and drink every day, so there’s a lot to talk about. You can learn about your besties or get to know someone you just met. Discuss your favorites, or share the foods and drinks you want to try. You might find some interesting things you have in common.

   • What’s your favorite food?
   • What’s your favorite drink?
   • What food should be banned from the cafeteria?
   • If you had to eat one food every day for a year, what would you pick?
   • What ingredients would you put in a perfect ice cream sundae?
   • What’s your go-to drink at Starbucks?
   • What was your favorite childhood cereal?
   • What’s your favorite fast food place?
   • Where would you go to eat on a first date?
   • What snack do you always get at the movies?
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18

Social Media Posts

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   You and your friends probably spend a lot of time on social media. Between the things you post and the things you share, there’s probably a lot to talk about. Check your friends’ feeds to see what they’ve been up to lately, then ask them about it.

   • How was that party you posted about?
   • Have you seen this meme?
   • What did you think about that article you shared?
   • Which of the quizzes you took today was most accurate?
   • What filter do you wish they’d make?

Conversation Starters for Friends

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• Remember your friends’ interests so you can ask questions about them.
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• Really listen to what your friends have to say. Your conversations will be so much more interesting and fun if you’re totally engaged with each other.
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Warnings

• You don’t need to overshare about yourself to get close with your friends. In some cases, oversharing can actually make people pull away.
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