Science of People - Logo

300+ Deep Questions To Keep The Conversation Going

Subscribe to our weekly newsletter

Please enable JavaScript in your browser to complete this form.

Every part of life relies on conversations. They’re how you bond with your family, keep up with friends, and make new connections. It can feel challenging to maintain those relationships if you’re more introverted or don’t know what to talk about. 

Use this guide to keep the conversation going with deep questions that are more interesting than small talk. You’ll get to know the people in your life and develop authentic relationships that make life more meaningful.

What Questions to Ask to Keep a Conversation Going

Consider asking follow-up questions based on your conversation partner’s answers. It prompts them to speak their mind, which is essential to getting to know someone.

Quote 2: “Practice active listening to hear what your conversation partner is saying while remaining present in the conversation.”

300+ Conversation Starters for All Occasions

Anyone looking for good questions to ask to keep a conversation going can use these ideas with anyone. They’ll develop meaningful connections with friends, partners, and co-workers. Try them today to see what works best for you.

To Make Someone Feel Good

Which of your accomplishments makes you most proud?

Talking about your proudest moments or achievements might put you at ease because it gives you a burst of confidence. Give your conversation partner the same experience by prompting them to talk about what they’ve achieved.

  1. What’s a recent success you’re still celebrating?
  2. What’s the best goal you’ve achieved?
  3. What comes to your mind when you think of success?
  4. How has someone been integral to your success?
  5. Who’s your hero?

To Get to Know Someone’s Background

What did you love doing as a kid?

Most kids grow up with one or two particular hobbies that morph into their identity. Your conversation partner may love talking about those things, like how they painted rocks they found in their backyard or hosted bike races with neighborhood friends.

You could also guide this conversation toward nostalgic toys. Ask if they had classic playthings like Hot Wheels, a Skip It, or Heelys. It’s one of the best questions to ask over text to keep a conversation going because everyone has that one toy they loved playing with or wanted more than anything. The conversation could stretch into the early morning hours if you discuss everything you enjoyed as a kid.

Fun Tip: You can always look up famous toys or games from childhood by searching the internet for the decade’s top playthings. What you find will become mini conversation prompts that won’t feel like a Q&A session because each name will spark a new memory.

  1. Which book did you love as a kid?
  2. What’s a life lesson you learned from one of your teachers?
  3. What’s the craziest event your high school was known for while you were there?
  4. Did you ever get an award in middle school?
  5. What’s something you tried out for in high school?
  6. What was your favorite story as a kid?
  7. What’s something about your family that made your childhood great?
  8. What was your first memory?
  9. Did your parents or family members ever make up a special song for you?
  10. Did you ever own a VCR player?

What did your younger self think was hiding in the dark?

It’s easy to laugh about childhood fears like the monsters that hid in the closet every night. Asking this question could also lead to conversations about how you got over your fears, revealing how your conversation partner learned to overcome what worries them in adulthood.

  1. Who do you look up to the most in your family?
  2. What’s your earliest memory?
  3. What’s one smell that takes you back to your childhood?
  4. What’s the weirdest dream you had while you were growing up?
  5. What movie did you watch more than three times as a child?
  6. What trend were you obsessed with as a kid?
  7. What were your siblings like?
  8. What was your favorite family vacation?
  9. Did you prefer having a birthday party or going to a birthday party?
  10. Were you and your friends on social media in middle school?

Who was your childhood best friend?

Young kids bond over almost anything, so talking about your childhood best friends is a great peek into a person’s past. They might also keep in touch with that friend if they’re excellent at maintaining relationships. This is a great place to start if you need questions to keep a conversation going with a guy or anyone else.

  1. What was your favorite Halloween costume?
  2. What was it like when you hung out with your cousins?
  3. What’s the strangest thing you believed as a kid?
  4. What tradition did you love most as a child?
  5. What was a childhood dilemma that makes you laugh now?
  6. What’s your favorite memory from elementary school?
  7. What’s one way you rocked your sense of style in middle school?
  8. Did you ever decorate your locker?
  9. What food did you refuse to eat?
  10. Did you ever move as a kid?
  11. Which clique did you fit into in middle school?
  12. Which candy did you most look forward to getting from trick-or-treating?
  13. What was the best backpack you had in grade school?
  14. What’s your favorite childhood food and why?
  15. What was your least favorite show as a kid?
  16. What’s a childhood fear you overcame?
  17. Who taught you to ride a bike?
  18. Did you ever look up to anyone in your class?
  19. What was your favorite pair of shoes as a kid?
  20. Which was better—going back-to-school clothes shopping or school supply shopping?
  21. What was the best part of your day in elementary school?
  22. What cartoon character did you most resonate with?
  23. Which seat on the school bus did you prefer?

To Find Out Someone’s Tastes

What’s a recipe you love cooking?

When you have some free time in the kitchen, you may have a favorite recipe that makes others pause. Consider the most unique or strange combination of foods and offer your own example if your conversation partner can’t think of anything.

  1. What vibes do you get from your Instagram feed?
  2. Have you ever developed an acquired taste for an unpopular food or drink?
  3. What do you consider an acquired taste?
  4. What’s the craziest dare you ever accepted at a sleepover?
  5. Have you ever owned a bug as a pet?
  6. What’s one drink you used to hate and now love?
  7. What food would you like to acquire a taste for one day?

To Find Out Someone’s Hobbies

What’s the coolest piece of tech in your home?

Technology is an investment, even if it feels like a hobby. Your conversation partner may want to discuss everything their latest purchase can do. You might even find you want one if you also love tech.

  1. What’s the most unusual hobby you’ve ever tried?
  2. What’s something you created, and how did you make it?
  3. What’s a crazy class you took in college or high school, and why?
  4. What’s something you did during a talent show?
  5. What do you think is the strangest hobby?

To Dive Deeper

  1. What’s your Sunday philosophy?

People almost always give their Sundays a purpose. Ask your conversation partner what they always do on Sundays and why it’s important to them. You’ll get a deeper look into their values and see if your Sunday philosophies match.

  1. Do you get the Sunday scaries?
  2. How do you prepare yourself for a new week?
  3. How do you think people should spend their Sundays?
  4. Are weekends for resting or getting things done?
  5. What’s the worst way to spend your Sunday?

To Get to Know Pet Peeves

What’s a habit some people have that grosses you out?

Some people may be uncomfortable talking about their own bad habits with someone they don’t know. It’s easier to talk about what bugs them in other people’s behaviors. You can bond over shared dislikes and venture into a deeper conversation after.

  1. What’s a bad habit you overcame?
  2. What would you have done differently in one of your previous relationships?
  3. What are two things you couldn’t live without?
  4. Which social media platform did you reluctantly start to enjoy?
  5. What’s your secret to breaking a bad habit?

A Fun Way to Get to Know Someone

Which Latin phrase best describes your adventurous spirit?

Latin phrases are more common than you might think. Your conversation partner might identify with things like carpe diem or veni, vidi, vici. After they answer, you can prompt them to explain the memory or reason behind the phrase and enjoy a longer conversation.

  1. Did you ever take Latin in school?
  2. Do you know any Latin?
  3. What’s the first Latin phrase that comes to your mind?
  4. Do you think people should still learn Latin in school?
  5. What’s a popular saying that sounds like it could have a Latin origin?

To Solicit Advice

If you could improve one thing in your life right now, what would it be and why?

Improving something in your life means you might have made a mistake or wish you’d done something differently. You might get some good advice and provide some of your own.

  1. How do you measure your success?
  2. Are adventures for learning or experiencing?
  3. What piece of travel advice do you wish someone had told you?
  4. What’s the best advice someone ever gave you and why?
  5. What kind of conflict resolution did you learn from your parents?

To Stimulate Growth

How have you changed over the last year?

The best people are always open to growth. Share a few ways you’ve changed over the year to learn how your conversation partner got to be their incredible self.

  1. What do you think is the best age?
  2. What’s your favorite number and why?
  3. If you could bring one board game to a party, which would it be?
  4. What’s your favorite aroma?
  5. What was your most heroic moment so far in your life?
  6. What’s an event that shaped your values?
  7. If you could go back in time and help someone, who would it be and why?
  8. Have you ever won an award?
  9. What person has contributed most to your life?
  10. How have you changed over the last year?

To See If You Could Vacation Together

Where’s the most beautiful place you’ve ever visited?

The most beautiful destinations leave a big impression on travelers. Ask your conversation partner which places have taken their breath away. You could also ask if they have pictures to keep the conversation going.

  1. What do you think is the most beautiful place in the world?
  2. What makes you look forward to a vacation?
  3. What vacations are on your bucket list?
  4. What historical destination did you most love visiting and why?
  5. What’s the most luxurious trip you’ve ever taken?
  6. What place changed your worldview?

Watch our video below to learn how to start a conversation with anyone with these killer conversation starters:

To Talk Jobs

What motivates you to work hard?

If your conversation partner loves their job, they’ll find motivation within their role. Ask what motivates them to learn about their career and what drives them.

  1. What’s the best thing about your job?
  2. Would you travel for your career?
  3. How many jobs have you worked throughout your life?
  4. What was your best job ever?
  5. How has your career affected your previous relationships?

To Tap Into Their Behavior

What’s the best habit you’ve ever started?

People with great behaviors often hone their characteristics through good habits. Discover what makes your conversation partner so awesome by learning about their most prized practice.

  1. What brings you the most joy from your daily routine?
  2. If you had to dye your hair, what would it look like?
  3. Which popular slang phrase did you start saying ironically?
  4. Which part of your life will people remember most about you?
  5. Which life experience made you change yourself and why?

To Know How They Enjoy Life

Would you rather change your house or your car?

Although this question may seem simple, it leads to ever-expanding conversations. You might learn about hobbies a person would like to do at home or how they’d like to drive a different car. If you’re wondering what questions to ask to keep a conversation going, use this open-ended prompt and watch time fly by.

  1. Do you prefer rainy mornings or snowy mornings?
  2. What’s a suitcase hack you can’t live without?
  3. Would you prefer an all-inclusive cruise or a train trip?
  4. What’s a small change you wish you could make to improve your life?
  5. What’s the coolest event you ever received an invitation to?
  6. What experience changed your life in college?

To Find Out the Basics 

Do you check the weather daily?

If someone regularly checks the weather, they likely prefer to plan their days. Find out if your conversation partner is a planner or more spontaneous by asking if they’re updated on the forecast.

  1. When has the weather changed your travel plans?
  2. Did you ever think about being a meteorologist?
  3. Which season best fits your personality?
  4. Which place in the world has the best weather?
  5. What do you do when a change in the weather disrupts your travel plans?

To Find Out How They Have Fun 

What’s your current favorite podcast?

Podcasts are the modern radio. They’re where people go to listen to celebrities, influencers, and broadcasters when they’re on the road. Share your favorite podcasts to bond over what you listen to in the car.

  1. Which music genre do you have on repeat?
  2. Which radio station do you listen to when you’re homesick?
  3. What station did you listen to when you first got your driver’s license?
  4. Do you have a radio app on your phone?
  5. Did you ever listen to the radio through a boombox?

To Discuss the World of Video Games

Have you ever played animal-based video games, and if so, which ones?

If your conversation partner loves animals and plays video games, they may have experience with games involving pets. They could talk about older games where they worked as a veterinarian or dog walker that link to great memories they rarely get to discuss with people.

  1. Which video game is overrated?
  2. Which company makes the best video games?
  3. Do you prefer playing video games alone or with friends?
  4. What’s your preferred way to play video games — on a console or computer?
  5. What’s a video game you wish you had discovered sooner?
  6. Which video game would you take on vacation and why?
  7. What’s your current favorite video game?

To Bond Over Family Memories 

What nickname do your family members call you, and how did you get it?

There’s always a story behind a childhood nickname. Ask your conversation partner about theirs, and you’ll learn something fun about them that wouldn’t come up in typical conversations.

  1. What’s your family’s longest-running tradition?
  2. What was your family known for in your neighborhood?
  3. What’s a family vacation you wish everyone could have taken together?
  4. What’s one way your family pet brought your loved ones together?
  5. Which cousin felt more like a sibling to you?

To Consider Hobbies From a New Perspective

How did you spend your last free hour?

People often plan for big weekend trips, but it’s also good to know how someone spends their free time at home. You’ll learn how they like to relax and connect over shared preferences.

  1. What’s your favorite object that you own?
  2. Have you ever taken a hobby class just for fun?
  3. What’s a car you’d love to drive one day?
  4. Did you ever perform in a show?
  5. What’s a hobby you’d enjoy doing with a partner?
  6. What’s a surprising type of tech that people don’t know you’re interested in?
  7. What’s one piece of technology you couldn’t live without?
  8. What was the coolest computer you ever used as a kid?
  9. What was your first cellphone?

What’s one way technology has impacted your life negatively?

Sometimes people develop hobbies they regret. Your conversation partner may have started a tech-based hobby that turned out to be less helpful than they thought.

  1. What’s a fictional piece of sci-fi tech you’d love to use in real life?
  2. What outdated technology do you wish people would bring back?
  3. Is technology developing too fast or not fast enough?
  4. Do you use instruction manuals when you get a new piece of technology?
  5. What tech development should win an award?
  6. How much do you depend on your phone?
  7. Are you a laptop or desktop computer type of person?
  8. Do you wish you could learn a programming language?
  9. What do you think is the greatest tech invention, and why?
  10. What’s an invaluable way your computer makes your life better?
  11. When did you get your first smartphone?
  12. Are you a PC or Mac person, and why?

Did you ever have a Myspace page?

Social media may not feel like a hobby, but it’s how many people spend their free time. Ask a throwback question to find out if your conversation partner ever updated their Myspace page as a fun hobby.

  1. Are you the friend people go to with a tech question?
  2. What’s your favorite account you follow on social media?
  3. What was the best ringtone you ever had?
  4. When did you get your first laptop?
  5. Do you use a tablet, and if so, how?
  6. What’s the weirdest thing you searched online for as a kid?
  7. Would you rather get a text or a phone call?
  8. How would you describe your social media feed in one word?
  9. How do you pronounce GIFs?
  10. Are you interested in virtual reality? 
  11. Has technology made people smarter?

What’s a hobby you’d like to learn?

Your conversation partner might not have enough free time to start all the hobbies that interest them. Encourage them to tell you about one of their dream hobbies to learn about the activities that capture their interest.

  1. Which influencers do you follow related to your hobby?
  2. Have you ever thought about turning your pastime into a job?
  3. What’s a historical fact about your hobby that blew your mind when you learned it?
  4. What pastime would you start doing if you had more hours in the day?

To Talk About Your Favorite Movies

What was the last film you saw?

Whether your conversation partner saw a movie in the theaters or streamed one at home, they might love discussing it. You can find out if you share a love for the same picture or if you want a film to end differently.

  1. What’s the most romantic movie to watch on a date?
  2. Which movie deserved a better reception when it debuted?
  3. What’s your favorite cult classic film?
  4. What’s a movie you wish you could have starred in?
  5. What’s a movie you still own as a DVD?

To Bond Over Fashion

How would you describe your fashion aesthetic?

If someone invests money into their aesthetic, they’ll likely enjoy talking about it. Ask your conversation partner what vibes their clothing gives and how they feel it expresses their personality.

  1. How often do you get new clothes?
  2. Would you ever learn to make your own clothes?
  3. Do you prefer shopping at thrift stores, department stores, malls, or online apps?
  4. What’s the one piece of clothing you wear most often?
  5. What’s a hand-me-down you loved?

To Reminisce About the Last Concert You Saw

Which musician do you wish you could see in concert?

It’s fun to bond over a shared love for the same artists or similar types of music. Use the opportunity to bookmark possibilities, like mentioning how you’d love to try it sometime with them at a future date.

  1. What was the last concert you saw?
  2. What was the last song you got stuck in your head, and what did it mean to you?
  3. Which show from history do you wish you could have attended?
  4. What’s something that would make every concert more enjoyable?
  5. What’s the most expensive concert ticket you have ever bought?

To Delve Into the Last Book You Read

Which book series should get its own TV series or movie?

This is one of the best questions to ask to keep a conversation going. Your conversation partner likely has a favorite book series they’d love celebrated in another form of media. It’s also an opportunity to learn why it matters, like why the themes or character arcs matter so much.

  1. What was the last book someone recommended to you?
  2. How often do you enjoy the books you read?
  3. Are you an audiobook person?
  4. How often do you check books out from your local library?
  5. Do you save your page by folding the corner or using a bookmark?

To Find Out How You Share the Same Friend

What do you and our shared friend have in common?

It’s always fun to find out how someone knows one of your friends. You can share stories about how you met and bonded over your love for your shared acquaintance.

  1. How did you meet our shared friend?
  2. What’s your favorite memory with our shared friend?
  3. Who was the best person you met through our shared friend, and why?
  4. Have you and our shared friend ever traveled together?
  5. What’s a cool gift you’ve given our shared friend?

To Relive the Best and Worst Moments

What’s your biggest fear?

Asking this question also poses the question—what does someone consider to be the biggest risk? You’ll learn much more about them by venturing into darker territory together. You’ll dive deeper into a relationship with a potential friend or partner when you let down your guard.

  1. What is the last place you’d ever want to visit and why?
  2. Where is the best place to go in the winter?
  3. Which hotel brand is your least favorite and why?
  4. What’s something you’re grateful for?
  5. What are the best and worst social media apps?

What’s the best and worst airline?

People have had good and bad experiences with airlines and often want to talk about them. You can ask one of these questions to keep a conversation going if your conversation partner has had more than their fair share of flights.

  1. What’s something you hope never to experience again?
  2. What’s the most dangerous thing you’ve ever accidentally done?
  3. What do you think is your best quality?
  4. What’s the worst flavor you’ve ever tasted?
  5. What would the best day ever look like?

What’s the worst haircut you’ve ever had?

There are many possible questions to keep a conversation going over text, but asking about previous haircuts can be one of the most entertaining. You might even get a picture of your conversation partner’s crazy hair if they’re up for it.

  1. What’s the worst date you’ve ever been on?
  2. What do you think is the most attractive thing about yourself?
  3. What’s the worst piece of clothing you’ve ever worn?
  4. What’s the most special item you’ve ever bought?
  5. What was the best birthday present you ever received?

To Talk About the Last Film You Saw

What recent movie were you most excited to see?

People start looking forward to movies when they see cast announcements and trailers. It takes a while to finally see the film, so your conversation partner will likely have lingering excitement about the movie that last intrigued them.

  1. What’s the last movie you saw in theaters?
  2. Who’s your favorite actor from the most recent film you saw?
  3. Do you think the last movie you saw will win any awards?
  4. Was the last film you saw inspired by a book?
  5. What’s a film that deserves a reboot?

To Enjoy a Conversation About Entertainment

Are you into any reality TV shows?

Reality TV can sometimes feel like a dirty secret. Admitting that you watch a reality TV show can break the ice and make your conversation partner more comfortable talking about the show they like.

  1. What’s the funniest thing you last saw in a TV show?
  2. Do you find yourself inspired by any travel YouTubers?
  3. Do you follow celebrity gossip?
  4. Which celebrity magazine did you like the most?
  5. Which public figure posts the most entertaining Instagram stories?

To Discuss the News

What’s a crazy tech headline you recently read?

Tech fans may keep up with news headlines regarding advancements in phones, laptops, robots, and more. Talking about the latest developments might allow them to discuss technology in ways that don’t come up in daily conversations.

This is one of the questions to ask over text to keep a conversation going, primarily because your conversation partner can send links to various news articles. Inquire about the latest discoveries, world records, or products to keep them talking. You’ll focus on their primary interest and even learn new things.

Pro Tip: Don’t be nervous about asking questions about technological terms or things you don’t understand. Your conversation partner may be more than happy to explain so you stay as interested in the topic as they are.

  1. What’s the most interesting thing you read in the last week?
  2. Do you read your local newspaper?
  3. Have you ever been featured in the news?
  4. What type of news do you find most interesting?
  5. What niche interest excites you when it pops up in the news?

To Mention Current Events

How do you think technology will make your life better in the next decade?

This question invites your conversation partner to daydream about the latest tech advances making the world a better place. They can imagine how their interests will develop over time and ways their life could improve simultaneously. You may even hear about their dreams or life plan, which creates bonding opportunities.

  1. Are you part of any hobby clubs in town?
  2. Which popular trend most annoys you?
  3. What local festival do you love attending in your hometown?
  4. What’s something you recently heard about and haven’t discussed with anyone?
  5. What’s an international event you’ve been following?

To Connect Over Movies, Television, and Books

What’s your most controversial opinion about movies?

This question often sparks hilarious social media posts because it’s supposed to garner lighthearted answers. Ask your conversation partner which movie opinion they have that most people disagree with, and you’ll likely have a laugh together.

  1. Which book do you think is underrated?
  2. What movie helped you make a great memory?
  3. Which TV show have you watched from beginning to end multiple times?
  4. Which book series do you love to reread?
  5. Have you ever visited a place based on a book, movie, or TV show?
  6. Do you prefer digital or audiobooks over printed books?

To Enthuse About Fashion and Beauty

Which fashion trend do you wish would come back?

Think back over your life and consider the fashions you’d like to wear again. Whether your conversation partner reflects on jelly shoes or scrunchies, they’ll likely think of something that sparks a shared interest with you.

  1. What’s a beauty trend you tried and didn’t like?
  2. Who’s the most fashionable person you know?
  3. What inspires your fashion aesthetic?
  4. What’s your secret to maintaining your fashion or beauty on a budget?

To Spark Love and Romance

How would you help a partner become their best self?

The best romantic relationships thrive because each partner helps the other reach their dreams. Your conversation partner may be a potential love interest if they express a passion for doing the same in their relationships.

  1. What’s a joy you like experiencing with your partner?
  2. What qualities make the best partner for you and why?
  3. What do you want to achieve with a partner?

When was the last time you laughed with a partner?

Complaining about past relationships with a current partner is easy, but there might have been moments worth celebrating too. Whether you need questions to keep a conversation going with a guy or anyone else, reminiscing about happy moments also gives you a peek into what might make your partner happy now.

  1. What do you think it means to be on your best behavior during a date?
  2. How do you handle heartbreak?
  3. What’s something you want to know about me?

Do you believe in couples counseling?

This might be the most thought-provoking of all the potential questions to keep a conversation going with your crush. If you aren’t on the same page about the power of counseling, it could prevent future healing if you become long-term and experience hardship.

  1. Do you picture yourself getting married?
  2. Why did your last relationship end?
  3. Have you ever taken a love language quiz?
  4. What’s the most important trait for your partner to have?

What’s the nicest thing a partner has ever done for you?

It’s easy to complain about ex-partners, but it’s more fun to talk about the ways you’ve felt loved in the past. Your conversation partner might have fond memories of the fantastic things someone did to express their love.

  1. Do you think one partner should become a stay-at-home parent when a couple has a baby?
  2. Do you believe in a lifetime of monogamy?
  3. Would you discuss an important decision with a partner even if you felt confident about what to do?

Do you have a romantic type in a partner?

It’s easier to get closer to your partner when they discuss what they find most romantic in their love interests. Make them feel extra special by treating them to whatever makes their heart skip a beat, like planning a date night or taking care of household chores.

  1. Do you think everyone has a soulmate?
  2. How would you define romance in a single sentence?
  3. Have you ever planned a trip as a surprise for a previous partner?

How would you plan your dream date if you had an unlimited budget?

Give your date room to daydream by considering how they’d spend the ultimate day with you. It’s a great open-ended question that teaches people how to keep a conversation going without asking questions.

To Converse About Your Health and Well-Being

What’s one word that describes you?

Picking a single word to describe your entire personality likely means it stems from a core memory or value. It’s one of the best questions to ask to keep a conversation going without needing more icebreaker topics.

  1. Does traveling help your mental health?
  2. How would you define your well-being?
  3. What helps you trust someone?
  4. How does gratitude fit into your well-being?
  5. What’s your favorite form of self-care?

To Dream About the Future Together

What’s your biggest personal dream?

People love talking about what motivates them. Dreams help people wake up in the morning and stay on track toward their vision of their future. Asking about which of their goals they’re most excited about could put someone more at ease so they’re ready to talk.

This is also a great conversation prompt for different settings, like networking events or brunch dates. It’s an appropriate topic for anywhere because it’s personal without crossing romantic or familial boundaries.

  1. Would you travel across the ocean by boat one day?
  2. What’s something you’d still like to accomplish in your life?
  3. What’s one thing you hope to experience in the future?

What’s one weird fear about technology that you have?

As much as people can love technology, they may also have a few concerns. This question prompts people to talk about how robots could take over the world or operate their home appliances unsupervised. It keeps the conversation light while moving in a new direction.

  1. How do you want to spend your retirement years?
  2. Do you want kids to be part of your future?
  3. Do you want a big wedding?
  4. What kind of parent would you become?
  5. What would your dream life look like if you found your soulmate?

What’s one way a futuristic robot could make your life easier?

When you need to know what questions to ask to keep a conversation going, ask a tech-minded person to invent a robot for their daily life. You’ll learn more about what they do and how their creative mind works.

To Touch on Sports

Which sports team do you keep up with even when you’re out of the country?

The most dedicated fan will track how their favorite team is doing even when they’re in a different time zone. Give your conversation partner room to talk about the team they love most by asking this question.

  1. Which sports team would you travel to see and why?
  2. Which sport do you prefer to see in person rather than on TV?
  3. Have you ever played a sport?
  4. If you could go professional in any sport, which would it be, and why?

To Broach Food, Jobs, and Work

What would have been your backup career?

Many people have backup plans for their careers. You never know when you’ll get laid off or have doors open to new opportunities. Ask your conversation partner what they’d also like to do for a living, and you’ll learn more about their unmentioned interests.

  1. What’s your favorite underground restaurant?
  2. Which dessert would you make on a baking competition show?
  3. What’s a snack you bring on every road trip?
  4. What was a crazy experience you had on a job?
  5. What’s the last new restaurant you tried, and how was it?

To Relive Your Travel Dreams

How do you spend your weekends?

You can ask many good questions to keep a conversation going, but this open-ended option is a great place to start. You’ll learn how an adventurer wants to spend their weekly chunk of free time and potentially know how you could join them one day.

  1. Which travel habit do you wish you could kick?
  2. Do you prefer solo or group travel?
  3. How do you decide where to go on your next adventure?
  4. What’s the coolest parade you’ve ever seen?
  5. What’s the biggest city you’ve ever been in?
  6. How often do you turn off your devices?
  7. Are you an online or in-person shopper?
  8. How would you spend your time if the internet disappeared?

What’s your favorite money-saving travel budget hack?

This is one of the most fun questions to keep a conversation going with your crush. While they talk about their favorite way to travel, you can daydream with them about experiencing those things together one day.

  1. Are you an aisle, middle, or window seat passenger on an airplane?
  2. What’s the luckiest thing that ever happened during one of your trips?
  3. How long do you prefer to travel for each vacation?
  4. Have you ever ridden the same roller coaster twice in a row?

Do you capture pictures while you travel or leave your phone in your pocket?

Some people are better at remembering to take pictures on vacations than others. If your conversation partner loves snapping photos, you can always ask to see a few from their recent trip to make your discussion last longer.

  1. Do you research everything yourself or plan trips with a travel agent?
  2. Do you ever get homesick?
  3. Where did you go on your last adventure?
  4. Have you ever traveled with someone you didn’t previously know?

How much luggage do you typically bring on vacations?

You’ll likely have a good laugh while chatting about how you both travel. Some people can magically make everything fit in one bag, while others travel with many. You might even learn some packing tips by bringing this topic up.

  1. What’s the most relaxing place in the world for you?
  2. What international event is on your bucket list?
  3. Do you learn the local language before traveling somewhere new?
  4. What historical event would you experience if you had a time machine?

What’s a place in this country you’d like to visit?

Whether you want questions to keep a conversation going with a girl, guy, or nonbinary person, asking where they’d like to visit is a great way to get them talking. You might even have the same U.S. destinations on your bucket list, which makes them more enjoyable to discuss.

  1. If you could only stay in hotels or rental properties for future trips, which would you choose and why?
  2. When was the last time you almost missed a flight?
  3. What’s the longest time you’ve spent on a single airplane?
  4. What was your best vacation ever?

To Connect Over Your Pets

Are you a dog or a cat person, and why?

The best questions to keep a conversation going with a girl, guy, or nonbinary person always align with their interests. Asking if they like dogs or cats could prompt them to delve into their past. Maybe they prefer one over the other due to their family history or a sweet memory that made them bond with a pet.

It’s also more of an open-ended question than you might think. Your conversation partner might not prefer either. If they don’t, you can encourage them to talk more about their favorite animals or the pets they wished they had.

You’ll instantly bond with someone if they share your love for dogs or cats. Bring up this easygoing discussion topic, and you’ll get to know someone better than if you asked how their day was going.

Fun Tip: Use this opportunity to show off your favorite pictures or videos of your pet. If your conversation partner loves the same animal as you, they’ll get more joy from seeing those pictures than just talking.

  1. What’s the strangest pet you have ever owned?
  2. Do you wish you grew up with more pets?
  3. What’s a crazy story about your family pet?
  4. Have you ever owned a fish?
  5. Did your family ever bring home a stray cat?
  6. Were you the neighborhood pet sitter?
  7. Did you ever try to start a dog-walking business as a kid?
  8. Do you have a pet now?

What’s a fictional animal you wish you could live with and why?

Book lovers and movie fans may easily pick a fictional animal they would love to live with. Their answer will depend on their preferred genres and favorite storylines, but you could still find a shared interest in more niche discussion topics like dragons or unicorns.

  1. Would you dress your dog up in sweaters?
  2. What’s your favorite part about caring for your pet?
  3. Has your pet ever helped you through a tough time?
  4. What pets were most popular in your neighborhood?
  5. Did you ever teach a family dog a new trick?
  6. What’s the cutest animal for a family pet?
  7. Are you allergic to any animals that people keep as pets?

What kind of personality does your pet have?

There are numerous questions to keep a conversation going over text, but asking about a pet’s personality is one of the easiest ways to get someone talking. Every quirk will likely come with a story, so the conversation flows naturally without too many questions.

  1. Would you own reptiles?
  2. What do you think cats dream about?
  3. Have you ever wanted to take home a cute zoo animal?
  4. Did your class ever have a classroom pet?
  5. Have you ever built a tube track for a hamster?
  6. Do you think dogs should sleep outside or inside?
  7. Have you ever had a pet run away, and if so, did you find them?
  8. Does one of your friends’ pets love you more than their owners?

Why Is It Important to Keep the Conversation Going?

Someone who can maintain a conversation can effectively engage with others, actively listen, and keep people interested while discussing various topics. They often have excellent interpersonal skills, making them an invaluable team member and social partner.

Guiding a conversation from beginning to end makes you a leader in your social groups. People will look up to you in the workplace because you know how to make your team members feel heard, valued, and actively included in conversations.

When Are Conversation Skills Most Helpful?

People are most grateful for conversation skills when meeting new people. Social anxiety can take the joy out of forming new relationships, even when you want to make a friend or meet a potential love interest. Although techniques like mindfulness can reduce the intensity1 of social anxiety, you can also become more confident by learning how to maintain an effortless conversation in these situations.

Quote 1: “Guiding a conversation from beginning to end makes you a leader in your social groups.”

Job interviews

So many things are on your mind when you sit down for a job interview. You want to showcase your skills and experience effectively, which can cause you to worry that you won’t fit everything into a short conversation.

You may also feel the stress of getting a job with a higher salary. The extra money could fund your dream adventures, reduce your financial anxiety, or help you advance to milestones like starting a family.

It’s easy to prepare for standard job interview questions, but the recruiter might also make small talk to get to know you better. Feeling assured in your ability to lead a conversation will help you make better impressions during these moments. You’ll feel confident about listening and responding to questions without making the conversation all about yourself.

Even if you don’t get to ask deep questions because the small talk portion of the interview passes by too quickly, you’ll still project the confidence the recruiter might search for in a good candidate. They’ll also note how you’ll fit in with their workplace compared to others who might be too shy to contribute to a team environment.

Consider a few of these questions to walk into your next interview with more confidence:

  • What’s one way technology has changed your career here for the better?
  • What’s the greatest office party you’ve ever attended here?
  • What’s one word that describes the camaraderie in this workplace?

Pro Tip: If you’re ready to say goodbye to those anxious job interview butterflies, try our Conversation Mastery course. You’ll gain access to prompts, video modules, and a workbook so you can start captivating conversations in any setting.

First dates

Even if you’ve talked with a potential first date over a dating app for a few days, meeting in person can create the potential for awkward silences. It is easier to talk over text because your potential partner isn’t right there waiting for you to say something.

Learning about and practicing conversation prompts will give you the confidence to use awkward silences to think of meaningful topics worth waiting for. You’ll know how to create deeper connections by finding common ground and building trust through tone and body language.

Your date nights are about to get much better if you start the evening with one of these thought-provoking questions:

  • What’s the coolest pet you’ve ever owned?
  • What’s the most relaxing place in the world for you?
  • What’s a niche type of news story that makes you excited?

Parties with friends

You might feel at ease while hanging out with one of your close friends, but anxiety can arise when they host a party with people you haven’t met. That’s when it’s most helpful to know questions to keep a conversation going. You’ll be able to connect with anyone based on topics that work with people from all walks of life.

Break the ice with questions like these that instantly help everyone bond:

  • What’s the craziest experience you’ve ever had while working?
  • Did you ever create your own ringtone, and if so, what was it?
  • Have you ever performed in a show?

Fun Tip: You can save conversation prompts on your phone so they’re always within reach. Even if your mind goes blank when talking to a stranger, you can avoid awkward silences by picking a prompt from your list.

How to Keep a Conversation Going Without Asking Questions

If you’re continually asking questions, your casual conversation or first date could feel like they’re on an unplanned interview. It might make them feel uncomfortable. That’s knowing how to keep a conversation going without asking questions is vital.

First, acknowledge any of your inner discomfort with silence. You may ask rapid-fire questions because you’re anxious about keeping the other person entertained. Acknowledge the silence to remove its power, then remind yourself that you are stronger than any fear.

Instead of asking more questions, share something about yourself. It could relate to the last question your partner answered or steer the conversation in a new direction. You’ll move the presumed spotlight onto yourself and eliminate any tension.

There’s also strength in knowing when a conversation can end. Give the other person space if they pull away from you. You could also thank them for meeting you on your date and say how much you look forward to your next one.

Takeaway: Improve Your Conversation Skills With Deep Questions

Anyone can become a better conversationalist. You only have to learn how to actively listen, overcome any fear of awkward silences, and bring up topics that engage your conversation partner, such as:

  • What vacations are on your bucket list?
  • What’s your favorite childhood food and why?
  • What’s your biggest personal dream?
  • What would have been your backup career?
  • What’s a hobby you’d like to learn?

Use these prompts to converse with anyone. As you practice your conversation skills, you’ll invent variations on these prompts to find what works best for those in your social circle.

Ready to branch out into new topics? Read about conversation starters related to upcoming calendar events or things perfect for texting between dates.

How to Deal with Difficult People at Work

Do you have a difficult boss? Colleague? Client? Learn how to transform your difficult relationship.
I’ll show you my science-based approach to building a strong, productive relationship with even the most difficult people.

Please enable JavaScript in your browser to complete this form.

Get our latest insights and advice delivered to your inbox.

It’s a privilege to be in your inbox. We promise only to send the good stuff.

Please enable JavaScript in your browser to complete this form.