550 Questions to Ask to Keep a Conversation Going

Ever hit that awkward silence and wondered what to say next? Worry no more! With the right questions up your sleeve, you can turn any chat from dull to delightful and keep conversations engaging, fun, and full of surprises. Let’s break the ice!

Table of Contents

Questions About Hobbies And Interests
Questions About Movies And TV Shows
Questions About Food And Cooking
Questions About Travel And Adventure
Questions About Social Media Trends
Questions About Technology And Innovation
Questions About Family
Questions About Friends
Questions About Work
Questions About School
Questions About Plans And Dreams
Questions About Art And Creativity
Questions About Cultural Experiences
Frequently Asked Questions
What are some basic tips for keeping a conversation going?
Conclusion

Questions About Hobbies And Interests

What do you like to do in your free time?
Do you have any hobbies you’re really passionate about?
How did you get started with that hobby?
What’s the best part about your favorite hobby?
Are there any hobbies you want to pick up?
What’s something you’re really good at?
Do you play any sports?
How often do you get to do your hobby?
Do you prefer indoor or outdoor activities?
Is there a hobby you gave up but wish you hadn’t?
What’s the most challenging thing you’ve ever done?
Do you like to cook?
What’s your go-to dish?
What’s your favorite type of music?
Do you play any musical instruments?
Have you ever tried any extreme sports?
Do you like to read?
What’s your favorite book?
What’s the last thing you made by hand?
Do you enjoy gardening?
Do you like to dance?
What’s the best place you’ve traveled to for fun?
Are you a fan of any sports teams?
What do you do to relax and unwind?
Do you enjoy painting or drawing?
Have you tried any online games?
What’s the last thing you learned just for fun?
Do you like puzzles or brain teasers?
Are you into fashion?
What kind of shows do you like to binge-watch?
Do you like photography?
Have you ever been camping or hiking?
Are you good at any card games?
Do you collect anything?
What’s a talent you have that not many people know about?
Do you enjoy doing DIY projects?
Are you into astrology?
Do you have any pets?
What’s your favorite board game?
Are you a morning person or a night owl?
What’s your favorite way to exercise?
Do you enjoy writing?
Have you ever tried acting or theater?
Do you like fishing or hunting?
What’s the most interesting museum you’ve been to?
Do you like to sing, even just for fun?
Are you good at trivia?
Do you enjoy swimming?
What’s a hobby you think is really unique?
Have you ever tried knitting or crocheting?
What’s your favorite type of dance?
Do you have a dream hobby you’d love to get into?

Questions About Movies And TV Shows

What’s your favorite movie of all time?
Have you seen any good movies lately?
What’s your favorite TV show?
What type of movies do you like?
Do you prefer comedies or dramas?
Have you ever watched a movie more than once?
What’s the worst movie you’ve ever seen?
Do you like to watch reality TV?
Have you ever binge-watched a series?
Do you have a favorite director?
What was the last movie that made you cry?
Are you a fan of any film franchises?
Do you like watching documentaries?
What’s your go-to movie snack?
Have you ever walked out of a movie theater?
Do you like watching foreign films?
Do you prefer watching movies at home or in the theater?
What’s your favorite animated movie?
Who’s your favorite actor or actress?
Do you like horror movies?
Have you seen any classic films?
Do you enjoy musicals?
What’s a show you thought you wouldn’t like but ended up loving?
Do you like mystery or thriller movies?
Who’s your favorite superhero?
What’s a movie that you think is overrated?
Have you seen any book-to-movie adaptations?
Do you watch talk shows?
Have you seen any movies based on true stories?
What’s your favorite comedy show?
Do you enjoy watching awards shows?
What’s a movie that really surprised you?
Do you like any crime dramas?
What’s a show you loved that got canceled?
What’s the most underrated movie you’ve seen?
Do you like period dramas?
What’s your favorite sci-fi movie?
Have you watched any mini-series?
Do you watch cooking shows?
What’s a movie that you love but others seem to hate?
What’s the last show you watched from start to finish?
Have you ever watched a show just for one character?
Do you like romantic movies?
What’s your favorite action movie?
Do you have a favorite movie quote?
Have you seen any films that made you think deeply?
What’s a show you can watch over and over again?
Do you enjoy watching sports on TV?
Have you seen any movies that made you laugh out loud?
What’s a movie or show you’re looking forward to watching?

Questions About Food And Cooking

What’s your favorite cuisine?
Do you like to cook or bake more?
What’s your signature dish?
Are you a fan of spicy food?
What’s your favorite dessert?
Do you enjoy trying new recipes?
Do you like to grill food?
What’s the most exotic food you’ve ever tried?
Do you have any food allergies?
What’s your favorite comfort food?
Do you enjoy seafood?
Are you good at making breakfast?
What’s the weirdest food combo you enjoy?
Do you have a favorite restaurant?
Do you enjoy meal prepping?
What’s your go-to snack?
What’s the first dish you learned how to cook?
Do you have a favorite kitchen gadget?
Do you like wine or cocktails with your meal?
Are you a coffee or a tea person?
Do you prefer dining in or eating out?
Have you ever taken a cooking class?
What’s the last thing you cooked?
Do you like smoothies or milkshakes?
What’s your favorite type of bread?
Do you enjoy eating healthy?
What’s your favorite fruit?
Do you like chocolate or vanilla better?
Do you enjoy making homemade pizza?
What’s a dish you want to master?
Do you follow any food blogs or chefs?
Are you a vegetarian or vegan?
What’s your favorite holiday dish?
What’s your favorite type of cheese?
Do you enjoy baking cookies?
What’s your favorite kind of cake?
Do you like cooking with herbs and spices?
Have you ever tried making your own pasta?
Do you like sweet or savory breakfasts?
Do you enjoy making soups?
What’s your favorite beverage?
Have you ever done a food challenge?
What’s your go-to late-night snack?
Do you like to make your own sauces or dressings?
What’s the most complicated dish you’ve ever made?

Questions About Travel And Adventure

Where’s your dream travel destination?
Have you traveled outside your country?
What’s your favorite travel memory?
What’s the longest trip you’ve taken?
Do you like road trips?
What’s the most beautiful place you’ve been to?
Do you prefer beach vacations or city trips?
What’s your favorite type of travel accommodation?
Are you a solo traveler, or do you prefer company?
What’s the next place on your travel list?
Have you ever gone backpacking?
Do you prefer planes, trains, or automobiles?
Have you ever been on a cruise?
Do you like adventure sports like skydiving or scuba diving?
What’s a place you would never go back to?
Do you speak any other languages?
What’s your favorite cultural experience from your travels?
Do you collect souvenirs?
Have you ever traveled for a festival or event?
Do you like taking photos when you travel?
Have you ever had a scary travel experience?
What’s your must-have travel item?
Do you like to plan your trips or be spontaneous?
Have you ever stayed in a hostel?
What’s the best local food you’ve tried while traveling?
Do you enjoy camping?
Have you visited any landmarks or natural wonders?
Do you prefer hot or cold climates for travel?
Do you have any travel traditions?
Have you ever done a volunteer vacation?
What’s the most remote place you’ve been to?
Have you ever seen the Northern or Southern Lights?
Do you enjoy hiking when you travel?
Do you like visiting museums and art galleries?
Have you been on any culinary trips?
Do you enjoy water activities like boating or snorkeling?
Have you ever gone on a safari?
Do you like exploring small towns or big cities?
Have you been to any theme parks while traveling?
Do you use travel guides or apps?
Have you ever traveled for work?
Do you have a favorite travel companion?
Have you ever traveled by bike or motorbike?
What’s the longest flight you’ve been on?
Do you like to explore off the beaten path?
Have you ever gone on a spontaneous last-minute trip?
Have you ever taken part in a guided tour?
What’s the most amazing wildlife you’ve seen on your travels?
Do you travel light or pack a lot of stuff?
Do you have any tips for getting through long flights or drives?
Have you ever visited a place totally different from what you expected?
Have you ever lost something important while traveling?
Do you have any funny travel stories?
Do you prefer active vacations or relaxing getaways?
Do you have a favorite travel app?
Have you ever had to use travel insurance?
Have you ever been to an all-inclusive resort?
Do you have a go-to travel playlist?
Have you ever met anyone interesting on a trip?
Do you enjoy the nightlife when you travel?

Questions About Social Media Trends

What’s your favorite social media platform?
Have you ever gone viral?
Do you follow any influencers?
What’s the latest social media trend you’ve tried?
Do you post often or mostly scroll?
Have you ever done a social media detox?
Do you use social media for work or just for fun?
What’s the most interesting hashtag you’ve seen lately?
Do you prefer stories or posts?
What was the last social media challenge you participated in?
Have you ever been part of a Twitter trend?
Do you watch live streams?
Do you use any social media scheduling tools?
Have you ever bought something because you saw it on social media?
Do you follow any meme accounts?
What’s the weirdest account you follow?
Have you ever tried to build a brand on social media?
Do you like video content or written posts more?
What’s your opinion on TikTok?
Do you ever participate in social media giveaways?
Have you ever had a tweet or post blow up?
Do you have a separate account for personal and public use?
How do you handle negative comments or trolls?
Have you ever attended an event because you saw it on social media?
Do you think social media is addictive?
How do you find new accounts to follow?
Do you use any filters or editing apps for your photos?
Have you ever been in a Facebook group that was super interesting?
Do you use LinkedIn for networking?
What’s your favorite type of content to consume?
Do you ever share political or controversial topics?
Have you ever made a friendship through social media?
Do you think social media is a good way to stay informed?
How long do you spend on social media each day?
Have you ever had to block someone?
Do you use any social media platforms for learning or self-improvement?
Have you ever tried creating a Reel or a short video?
Do you think social media has changed the way we communicate?
What’s your take on “cancel culture” on social media?
Do you follow any accounts just for the cute animal pictures?
Have you ever used social media to raise awareness for a cause?
Do you think social media affects mental health?
Do you follow any accounts that focus on positivity or motivation?
Have you ever discovered a new place to visit through social media?
Do you think social media fame is the same as real-world fame?

Questions About Technology And Innovation

Are you a tech-savvy person?
What’s your favorite gadget?
Do you think technology makes life easier or more complicated?
Have you ever built your own computer?
Are you interested in virtual reality?
What’s the most useful app on your phone?
Have you ever tried coding?
Do you prefer Android or iPhone?
Do you like smart home devices?
What’s the last tech product you bought?
Are you excited about any upcoming tech releases?
Do you think we rely too much on technology?
What’s your favorite video game?
Do you use a fitness tracker?
Have you ever backed a tech project on Kickstarter?
Do you own any cryptocurrency?
Are you worried about online privacy?
Do you use any productivity apps?
Do you watch tech reviews online?
Do you prefer ebooks or physical books?
Have you ever had a tech fail at the worst moment?
What’s your opinion on electric cars?
Do you have any favorite tech YouTubers?
Do you think robots will take over jobs?
Have you tried any augmented reality apps?
How do you keep your digital files organized?
Do you prefer texting or calling?
Have you ever lost important data?
Do you have any smart appliances in your home?
What’s your take on social media algorithms?
Do you think AI will have a big impact on our future?
Have you ever used a 3D printer?
What’s your favorite browser extension?
Do you have a favorite tech brand?
What’s your internet speed at home?

Questions About Family

How many siblings do you have?
Are you the oldest, youngest, or in the middle?
Do you have any family traditions?
What’s your favorite family holiday?
Are you close to your grandparents?
How often do you see your extended family?
Do you have family game nights?
What’s the best piece of advice a family member has given you?
Do you have any family recipes that you love?
What’s a typical family dinner like at your home?
How do you usually celebrate birthdays in your family?
Have you ever had a big family reunion?
Are you named after anyone in your family?
Did you grow up in a big or small town?
What kinds of pets did you have growing up?
What’s your favorite childhood memory with your family?
Is there a “black sheep” in your family?
Do you have relatives in other countries?
Are your parents strict or laid-back?
Do any of your family members have unique talents?
Do you look more like your mom or your dad?
What’s the most valuable lesson your parents taught you?
Have you ever traveled with your family?
Is there a family heirloom that’s special to you?
Do you have any cousins you’re close to?
Do you have family movie nights?
Have you ever worked in a family business?
What’s your funniest family story?
Who’s the storyteller in your family?
What’s a hobby that your family enjoys together?
Do your parents have any hobbies they’re passionate about?
Did your family have any pets when you were a kid?
Do you have any siblings that are your complete opposite?
What’s a family outing you really enjoyed?
Who’s the peacemaker in your family?
How do you resolve conflicts in your family?
Who’s the most tech-savvy in your family?
Do you have any favorite family photos?
What’s the best vacation you’ve taken with your family?
Do any of your family members have a big age gap with you?
Did you get along with your siblings growing up?
Is there a family sport that everyone likes?
Do you have any favorite stories from your parents’ or grandparents’ youth?
How do you keep in touch with family members who live far away?
Do you have any family in the military?

Questions About Friends

How did you meet your best friend?
What do you usually do when you hang out with friends?
Do you have a friend who’s like a sibling to you?
What’s the longest friendship you’ve ever had?
Do you have a friend who’s the total opposite of you?
Have you ever been on a trip with friends?
Do you have any friends from your childhood?
What’s the most fun you’ve had with a friend?
Do you and your friends have any special traditions?
How do you celebrate birthdays with your friends?
Do you have friends who live in different countries?
Have you ever helped a friend through a tough time?
What’s your favorite thing to do with a group of friends?
Do you have a friend who makes you laugh like no one else?
Do you share any hobbies with your friends?
Have you ever lived with a friend?
What qualities do you look for in a friend?
Have you ever had a friendship that ended, but you wish hadn’t?
Do you have friends from different walks of life?
What’s the most adventurous thing you’ve done with friends?
Have you ever had a misunderstanding with a friend that was resolved?
How often do you talk or hang out with your close friends?
Do you have a go-to friend for specific advice?
Do you make friends easily?
Have you ever been friends with a teacher or boss?
What’s the nicest thing a friend has ever done for you?
Do you prefer having a big circle of friends or a small, close-knit group?
Have you ever borrowed something from a friend and forgot to return it?
Do you and your friends have any inside jokes?
How do you handle disagreements with friends?
Do you have any long-distance friendships?
Have you ever reconnected with an old friend?
Do you keep in touch with friends from high school or college?
Have you ever gone to a concert with friends?
What’s your most embarrassing moment with friends?
Do you have a friend who challenges you to be better?
Have you ever met a friend online?
Do you have any friends in your neighborhood?
How do you usually make plans with friends?
Do you have a friend who you admire for their courage?
Have you ever surprised a friend on their birthday?
Do you have any friends who are incredibly creative?
Do you have a friend who’s really good at cooking?
Have you and a friend ever had a crush on the same person?
What’s the most meaningful conversation you’ve had with a friend?

Questions About Work

What do you do for a living?
Do you like your job?
How did you get into your line of work?
Do you work from home or go to an office?
What’s your favorite part of your job?
What’s the most challenging thing about your job?
Have you ever had a side hustle?
Do you have a good work-life balance?
What was your first job ever?
Do you have a mentor at work?
Are you friends with your coworkers?
What’s the most rewarding project you’ve worked on?
Do you have to travel for work?
Do you see yourself staying in this job long-term?
Have you ever had to fire someone?
What’s your dream job?
Do you usually dress up for work, or is it casual?
Have you ever had a really tough boss?
What’s the weirdest job you’ve ever had?
Do you listen to music while working?
How do you deal with work stress?
Do you enjoy office parties?
Have you ever been promoted?
What’s the best career advice you’ve received?
Do you like working on a team or alone?
Have you ever had to give a presentation at work?
What’s a skill you want to learn for your job?
Have you ever worked a night shift?
What’s the longest you’ve stayed at a job?
Do you prefer working for a small or large company?
Have you ever worked in retail or food service?
Do you have any work-related pet peeves?
Are you part of any professional organizations?
Do you think you’ll ever start your own business?
Do you have any cool work perks, like free lunch or a gym?

Questions About School

What was your favorite subject in school?
Did you enjoy high school or college more?
Have you ever had to pull an all-nighter for school?
Did you play any sports in school?
Were you part of any school clubs or organizations?
What’s the hardest class you’ve ever taken?
Did you have a favorite teacher?
Did you go to public or private school?
What was your go-to lunch in the school cafeteria?
Did you ever get into trouble at school?
Did you like taking exams or writing papers more?
Did you have to wear a uniform in school?
Did you ever go to summer school?
Were you friends with your classmates?
What was your most memorable school trip?
Have you ever studied abroad?
What’s the most interesting thing you learned in school?
Did you have a best friend in school?
Did you walk, bike, or ride to school?
Did you ever skip a class?
What did you do for fun during school breaks?
Did you ever win any awards in school?
Were you ever in the school band or orchestra?
Have you kept in touch with anyone from school?
What was your least favorite subject?
Did you have any subjects that were really easy for you?
Have you ever been to a school reunion?
Did you like your school’s mascot?
Have you ever had to change schools?
What were your school colors?
Did you go to your school dances?
Have you ever cheated on a test?
Did you ever have homework you just couldn’t figure out?
Did you ever participate in a school play or talent show?
What would you change about your school experience if you could?

Questions About Plans And Dreams

What’s on your bucket list?
Do you have any big plans for the next year?
What’s a goal you’re working toward right now?
Where do you see yourself in 5 years?
Do you believe in setting New Year’s resolutions?
What’s a skill you want to learn in the future?
Do you have any travel plans coming up?
Are you thinking about going back to school or taking courses?
What’s your dream job?
Do you have any plans for starting a family?
Are you saving up for something special?
Do you plan to move to a different place in the future?
Are you thinking about changing careers?
What’s a project you want to start?
Do you have any upcoming events you’re excited about?
Are there any upcoming movies or shows you’re looking forward to?
What’s something you hope to achieve by the end of this year?
Do you have any health or fitness goals?
Are you planning to take up any new hobbies?
Do you have a dream destination for a holiday?
What’s the next big milestone in your life?
Are you looking to get involved in community service or volunteering?
What’s a book you plan to read soon?
Do you have a five-year plan?
Are you considering starting your own business?
What’s a personal development goal you have?
Do you want to become fluent in another language?
Is there a big risk you’re considering taking?
What’s an adventure you’re hoping to go on?
Do you have any upcoming family events?
Are you planning to attend any concerts or festivals?
Do you have a timeline for achieving your dreams?
What’s something you’re saving up for?
Are you planning to renovate or redecorate your living space?
What’s a lifelong dream you’re still chasing?

Questions About Art And Creativity

Do you enjoy making art?
Who’s your favorite artist?
Have you ever visited an art museum?
Do you prefer modern or classical art?
What’s the last creative thing you did?
Do you have a creative hobby, like painting or writing?
Have you ever taken an art class?
Do you enjoy going to art galleries?
What’s the most unique piece of art you’ve ever seen?
Do you think art should always have a meaning?
Do you like listening to music while creating art?
Have you ever tried digital art?
What’s your favorite art medium: painting, drawing, sculpture, or something else?
Do you have any artwork displayed in your home?
Have you ever sold any of your artwork?
Do you have a favorite art movement, like Impressionism or Cubism?
Do you enjoy watching movies or shows about artists?
Have you ever tried street art or graffiti?
Do you like making crafts?
What’s the most challenging art project you’ve tackled?
Have you ever tried an art form from another culture?
Do you enjoy coloring books?
What’s your favorite color to use in art?
Have you ever visited an art fair?
Do you have a favorite book about art or creativity?
Do you like to sketch or doodle?
What inspires your creativity?
Do you ever listen to art podcasts or watch art YouTube channels?
Have you ever been to a live art event or show?
What was the last creative gift you gave someone?
Do you have a favorite artistic era?
Do you think anyone can be an artist?
What’s your go-to tool for creating art?

Questions About Cultural Experiences

Have you ever been to a cultural festival?
What’s the most interesting cultural tradition you’ve learned about?
Do you enjoy trying foods from different cultures?
Have you ever watched a foreign film?
What’s the most unique cultural experience you’ve had?
Do you know any other languages?
Have you ever worn traditional clothing from another culture?
Do you listen to music from different parts of the world?
What’s your favorite holiday, and how do you celebrate it?
Have you ever participated in a cultural dance?
Do you have any family traditions that are special to your culture?
Have you ever been to a religious ceremony from a different culture?
What’s the most surprising cultural difference you’ve encountered?
Have you ever been to a cultural heritage museum?
Do you have friends from different cultural backgrounds?
What’s the most interesting cultural artifact you’ve seen?
Have you ever read literature from another culture?
How do you feel about cultural appropriation?
What’s your favorite cultural story or myth?
Have you ever tried a cultural beauty or wellness practice?
Have you ever visited a place just to experience its culture?
Do you think your own culture influences your views and decisions?
Have you ever celebrated a holiday that’s not from your own culture?
What’s the most memorable cultural performance you’ve seen?
Have you ever cooked a dish from another culture?
Do you follow any cultural customs that aren’t from your own background?
Have you ever been to a wedding from a different culture?
How do you show respect in different cultural settings?
What’s the most culturally diverse place you’ve been to?
Have you ever learned a traditional craft or skill?
Do you enjoy learning about history and how cultures have evolved?
Have you ever volunteered in a cultural community center?
Do you know any folklore from other cultures?
Have you ever been part of a cultural exchange program?
What’s the most meaningful cultural experience you’ve had?

Frequently Asked Questions

What are some basic tips for keeping a conversation going?

Here are some simple tips to keep in mind:

Ask open-ended questions: Instead of questions that can be answered with “yes” or “no,” try asking questions that invite the other person to share more.
Listen actively: Show interest in what the other person is saying. Nod, make eye contact, and give feedback like “Oh really?” or “That’s interesting.“
Share personal stories: People usually enjoy hearing fun or interesting stories, which could encourage them to open up as well.

How important is it to find common interests?

Finding common interests is like hitting the jackpot in a conversation. It instantly gives you much to talk about and makes the interaction more enjoyable for both sides.

But it’s not the end of the world if you don’t have a lot in common. You can still have a meaningful conversation by showing interest in what the other person says, asking open-ended questions, and being a good listener.

What are some don’ts when trying to keep a conversation going?

Interrupting: Let the other person finish what they’re saying before you jump in.
Talking only about yourself: A conversation is a two-way street. Make sure to ask questions and show interest in the other person.
Being negative: Keep the conversation light and positive, especially if you’re just getting to know someone.

Any tips for keeping a conversation going in a group setting?

Group conversations can be tricky but also really fun. Here’s how to keep the ball rolling:

Include everyone: Try to engage as many people as possible by asking questions anyone can answer.
Listen and build: Listen to what others say and try to build on it. If someone mentions loving to travel, you can ask, “Has anyone here been to a place they’d recommend for a vacation?”
Know when to step back: In a group, it’s not all about you. Give others a chance to speak and shine.

Conclusion

So, you’ve got the tools; it’s time to use ’em! The next time you’re stuck in a “so, um, how about that weather?” kind of talk, whip out one of these questions.

Whether you’re curious about someone’s hobbies or dreaming big about the future, these questions will not just keep the conversation going—they’ll make it unforgettable. Happy chatting!