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150 Great Questions to Ask to Keep a Conversation Going

Last Updated on July 2, 2026 by Status.net Editorial Team

It can feel awkward when the chat starts to fade and you’re not sure what to say next, but with the right questions, you can keep any conversation flowing smoothly and make deeper connections with people. This article will give you lots of go-to questions for different situations. You’ll find ideas for chats with new people, friends, coworkers, and more!

Part 1Open-Ended Versus Closed Questions

Open-ended questions invite longer, more detailed answers. They start with words like “how,” “why,” or “what.” Closed questions usually get a short, specific answer like “yes” or “no.”

Examples of open-ended questions:

  • What’s your favorite childhood memory?
  • How did you get into your current job?
  • What’s the most exciting trip you’ve ever taken?
  • Why did you choose to live in this city?

Examples of closed questions:

  • Do you like travelling?
  • Have you ever been to Europe?
  • Are you a morning person?

Open-ended questions are often better for keeping the conversation going.

A closed question does not have to be a dead end. If someone answers “yes” or “no,” you can often turn it into an open-ended question with a quick follow-up. For example, “Are you a morning person?” can become “What does your morning routine usually look like?” This small habit, closing the gap between a closed question and a follow-up, is one of the easiest ways to keep a conversation from stalling.

Part 2Conversation Techniques to Keep the Talk Flowing

Good questions matter, but the way you use them matters just as much. Experienced conversationalists rely on a few habits that work in almost any setting, whether you’re chatting with a coworker, a new friend, or someone you’d like to date.

One helpful mental shortcut is the FORD method: Family, Occupation, Recreation, and Dreams. When you’re not sure what to ask, these four categories usually give you somewhere safe and interesting to go next.

The Art of the Follow-Up Question

A single question rarely carries a conversation on its own. What keeps the talk going is the follow-up, the question that shows you were actually listening and want to hear more.

  • What made you decide to do that?
  • How did that make you feel?
  • What happened next?
  • What was that experience like for you?
  • What do you think you’ll do differently next time?
  • Was that harder or easier than you expected?

When you notice someone light up while talking about a topic, that’s usually a sign to ask a follow-up rather than move on to a new subject. Following the energy in a conversation, instead of jumping between unrelated questions, is one of the biggest differences between a chat that fizzles and one that feels genuinely engaging.

Balancing Questions With Sharing About Yourself

Asking question after question can start to feel like an interview if you never share anything about yourself in between. In most conversations, it helps to follow this simple rhythm:

  • Ask a question.
  • Listen fully to the answer, without planning your next question while they’re still talking.
  • Respond with a short reaction or a related detail about your own experience.
  • Then ask your next question, ideally a follow-up connected to what they just said.

This back-and-forth rhythm keeps the exchange feeling like a genuine conversation between two people, rather than a one-sided line of questioning.

Questions to Ask to Keep a Conversation Going: Examples for Different Occasions

Asking the right questions can make your conversations more engaging and meaningful! Below you will find examples of great questions to help you keep the talk flowing in various settings.

Part 3Questions to Ask at Networking Events

  • What brought you to this event?
  • What do you enjoy most about your work?
  • What’s the biggest challenge in your industry right now?
  • How did you get started in your field?
  • What’s the most exciting project you’re working on?
  • What’s your favorite part of networking events?
  • What’s your go-to app for productivity and why?
  • How do you stay updated with industry trends?
  • What’s the best career advice you’ve ever received?
  • What’s your dream job?
  • What’s the most interesting place your work has taken you?
  • How has your industry changed since you started?
  • What skills do you think are most important in your field?
  • If you could learn any new skill, what would it be and why?

Part 4Questions to Ask at Social Gatherings

  • What’s your favorite local restaurant?
  • What’s the best vacation you’ve ever been on?
  • What’s your favorite way to relax after a long day?
  • If you could travel anywhere right now, where would you go?
  • What’s the best concert you’ve ever been to?
  • Do you play any sports or exercise regularly?
  • What’s your favorite season and why?
  • What was your first job?
  • Do you have any hidden talents?
  • What’s the most adventurous thing you’ve ever done?
  • If you could have dinner with any celebrity, who would it be?
  • What’s your favorite childhood memory?
  • If you could instantly become an expert in something, what would it be and why?

Part 5Questions to Ask in a Workplace

  • What project are you most excited about right now?
  • How did you end up in your current role?
  • What’s your favorite part of working here?
  • What’s the most interesting thing you’ve learned at work lately?
  • How do you like to celebrate your wins at work?
  • What’s your ideal work environment?
  • If you could switch jobs with anyone in the company for a day, who would it be?
  • What’s the best career advice you’ve ever gotten?
  • How do you stay motivated during busy periods?
  • What’s your go-to lunch spot near the office?
  • What’s the most challenging part of your job?
  • How do you unwind after a stressful day at work?
  • If you could add any perk to our workplace, what would it be?
  • What’s your favorite way to collaborate with the team?
  • What’s the most valuable skill you’ve gained in this job?
  • If you could create a new position at the company, what would it be?
  • What’s your proudest work achievement so far?

Question-of-the-Day Ideas for Team Meetings

Many teams open standup meetings or Monday check-ins with a quick question of the day. It warms people up before the real agenda starts and gives quieter team members an easy way to speak first.

  • What’s one small win from this week you want to share?
  • What’s a tool or shortcut that’s saving you time lately?
  • If you had an extra hour in your workday, how would you use it?
  • What’s a work habit you’re trying to build or break?
  • What’s the best meal you’ve had this week?
  • What’s one thing you’re looking forward to this month?
  • What’s a skill outside of work you’re proud of?

Part 6Questions to Get to Know Someone

Whether you’re chatting with a new coworker, a classmate, or someone you just met at a party, get-to-know-you questions give you a comfortable way to build a foundation before moving into deeper territory.

Basic Questions to Get to Know Someone

  • Where did you grow up?
  • Do you have any siblings?
  • What did you study, or what do you do for work?
  • What’s your favorite way to spend a weekend?
  • Are you close with your family?
  • What’s something you’re really good at?
  • What kind of student were you?
  • Do you have any pets?
  • What’s your favorite type of cuisine?
  • What was your major, and why did you pick it?
  • What neighborhood do you live in, and do you like it?
  • What’s something people are usually surprised to learn about you?

Questions to Get to Know Someone Deeply

Once the basics are covered, a few well-placed questions can move the conversation from small talk toward something more meaningful, without feeling forced.

  • What’s a belief you hold that most people would disagree with?
  • What does a good life look like to you?
  • What’s something you’ve changed your mind about recently?
  • Who in your life has shaped you the most, and how?
  • What’s a moment that changed how you see the world?
  • What are you most proud of that no one really asks you about?
  • What’s something you’re currently working on within yourself?
  • What do you need from people when you’re going through something hard?
  • What’s a fear you’ve managed to overcome?
  • What does trust mean to you?
  • What’s something you wish more people understood about you?

If a question about beliefs or fears feels too heavy for the moment, soften it with a lighter one first, like a favorite memory, before circling back.

Part 7Questions to Ask Friends and Family

Conversations with people you already know can sometimes stall simply because you assume you already know everything about them. A well-timed random question can surprise you both and bring a fresh energy back into the chat.

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Random Questions to Ask Friends

  • What’s the weirdest thing you’ve ever eaten on a dare?
  • If you had to eat one meal for the rest of your life, what would it be?
  • What’s a rumor you’ve heard about yourself?
  • What’s the dumbest argument you’ve ever had with someone?
  • If you woke up as a different animal tomorrow, which would you want to be?
  • What’s the most useless fact you know?
  • What’s a trend you never understood?
  • If you had to give up your phone or your car for a month, which would you choose?
  • What’s the weirdest thing in your search history right now?
  • What’s a smell that instantly takes you back to your childhood?
  • If your life had a theme song, what would it be?
  • What’s something you were convinced was true as a kid that turned out to be completely wrong?

Questions to Ask Siblings and Family Members

  • What’s your favorite memory of us growing up together?
  • What family tradition do you hope we keep for years to come?
  • If you could relive one family vacation, which one would it be?
  • What’s something you learned from Mom or Dad that you still use today?
  • If you won the lottery tomorrow, what’s the first thing you’d do for the family?
  • What’s a family story you never get tired of hearing?
  • What’s one thing you wish you’d asked our grandparents?
  • If you could go back and give your younger self one piece of advice, what would it be?
  • What’s a hypothetical you’ve always wanted to ask me?
  • What do you think makes our family different from others?

Part 8Questions to Ask Someone You’re Interested In

If you’re hoping to build a connection with someone new, thoughtful questions often work better than rehearsed lines. Genuine curiosity about a person’s life, sense of humor, and values tends to come across as far more attractive than trying to sound impressive.

Questions to Ask Your Crush

  • What’s something that instantly makes you laugh?
  • What’s your idea of a perfect date?
  • What first caught your attention about me?
  • What’s something you find really attractive in a person’s personality?
  • What’s a song that always puts you in a good mood?
  • What’s the most spontaneous thing you’ve ever done?
  • What are you looking for right now, in relationships or in life in general?
  • What’s a small thing that makes your day better?
  • What’s something you’re a little nerdy about?
  • What’s your favorite way to spend a lazy Sunday?
  • What’s something you’re looking forward to this year?

Questions to Ask Your Girlfriend, Boyfriend, or Partner

  • What’s your favorite memory of us so far?
  • What makes you feel most loved and appreciated?
  • What’s something you’d like us to try together?
  • What does a perfect weekend with me look like to you?
  • What’s something about me that surprised you when we first started dating?
  • How do you like to be supported when you’re stressed?
  • What’s a goal you’re working toward right now?
  • What’s your favorite thing we’ve done together this year?
  • What’s something you appreciate about our relationship that we don’t talk about enough?
  • What’s a habit of mine you find endearing?
  • Where do you see us a few years from now?

Romantic Questions for Date Night

  • What’s a moment from our relationship you replay in your head?
  • What’s something you’ve always wanted to try but never had the chance to?
  • What’s your love language, and how did you figure that out?
  • What’s a dream you have that we haven’t talked about yet?
  • What’s something small I do that means a lot to you?
  • If we could teleport anywhere right now for date night, where would you pick?
  • What’s a tradition you’d like us to start together?

A famous set of 36 questions, developed by researchers studying closeness, is built to move gradually from light topics to vulnerable ones. You do not need all 36 in one sitting. Borrowing a few from each stage of that idea, light, medium, and deep, can guide a date night conversation nicely.

Part 9Deep Questions to Keep the Conversation Going

Deep questions help build stronger connections by exploring thoughts, feelings, and experiences. They often touch on personal topics and values:

  • What’s the most important lesson you’ve learned in life?
  • Who has had the biggest influence on you?
  • What’s your biggest fear?
  • What makes you feel truly alive?
  • If you could change one thing about yourself, what would it be?
  • What’s your definition of success?
  • How do you want to be remembered?
  • What’s the hardest decision you’ve ever had to make?
  • What’s your biggest regret?
  • What’s the best advice you’ve ever received?

Hypothetical Questions to Spark Deeper Thinking

Hypothetical questions ask someone to imagine a situation rather than recall a memory. They tend to reveal values and priorities in a way that feels playful rather than heavy.

  • If you could master any skill overnight, what would it be and why?
  • If you had to move to a new country tomorrow, where would you go?
  • If you could relive one year of your life, which one would you choose?
  • If money were not a factor, what would you spend your time doing?
  • If you could send a message to your future self, what would it say?
  • If you could only keep three possessions, what would they be?
  • If you had to give a speech tomorrow with no preparation, what would you talk about?

Part 10Fun Questions to Ask to Keep the Conversation Going

Fun questions keep conversations light and enjoyable. They’re great for breaking the ice or adding some humor to a chat:

  • If you were a superhero, what would your power be?
  • What’s the weirdest food you’ve ever tried?
  • If you could have dinner with any celebrity, who would it be?
  • What’s your go-to karaoke song?
  • If you could instantly become an expert in one thing, what would it be?
  • What’s the most embarrassing thing that’s happened to you?
  • If you could travel back in time, which era would you visit?
  • What’s the strangest dream you’ve ever had?
  • If you were a flavor of ice cream, what would you be?
  • What’s the most useless talent you have?

Random and Silly Questions to Ask Friends

Sometimes the goal is simply to make someone laugh or groan. These work well when you’re bored, riding in a car together, or trying to lighten the mood after a serious topic.

  • Would you rather fight one horse-sized duck or a hundred duck-sized horses?
  • What’s the dumbest way you’ve ever gotten injured?
  • If you had to be renamed after a vegetable, which one would suit you?
  • What’s a food combination you love that grosses other people out?
  • If animals could talk, which one would be the rudest?
  • What’s the most ridiculous thing you’ve Googled this week?
  • If you had to wear one outfit for the rest of your life, what would it be?
  • What’s a weird habit you have that you don’t usually tell people about?

Would You Rather Questions

  • Would you rather be able to fly or be invisible?
  • Would you rather always be ten minutes late or twenty minutes early?
  • Would you rather give up your phone for a month or your favorite food for a year?
  • Would you rather live without music or without movies?
  • Would you rather know when you’re going to die or how you’re going to die?
  • Would you rather have unlimited money or unlimited time?

Part 11Conversation Games That Use Questions

Structured games take the pressure off coming up with the next question yourself. They work especially well with groups, on road trips, or whenever the energy needs a boost.

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20 Questions and 21 Questions

In 20 Questions, one person thinks of a person, place, or thing, and everyone else takes turns asking yes-or-no questions to guess it, within twenty questions. In the 21 Questions game, players simply take turns asking each other any question they like, often used as a lighter, more personal way to get to know someone new or flirt with someone you’re interested in.

  • Is it bigger than a car?
  • Is it something you can hold in your hand?
  • Would I find this in my house?
  • Is it a living thing?
  • What’s the last thing you do before falling asleep?
  • What’s your biggest turn-off in a person?
  • What’s a rule you’d break if you knew you wouldn’t get caught?

Truth or Dare and Never Have I Ever

Truth or Dare gives each player a choice between answering an honest question or completing a challenge, while Never Have I Ever reveals shared or surprising experiences without anyone needing to elaborate unless they want to.

  • Truth: What’s the biggest lie you’ve ever told?
  • Truth: Who was your first crush?
  • Truth: What’s something you’ve never told anyone in this room?
  • Never have I ever pretended to be sick to get out of something.
  • Never have I ever laughed so hard I cried in public.
  • Never have I ever forgotten someone’s name right after meeting them.

Trivia Questions for Friendly Competition

A few light trivia questions can break up a slow moment and get everyone talking, especially in a group where not everyone knows each other well.

  • Which planet is known as the Red Planet? (Mars)
  • What is the largest ocean on Earth? (The Pacific Ocean)
  • How many strings does a standard guitar have? (Six)
  • What is the smallest country in the world? (Vatican City)
  • What gas do plants absorb from the air? (Carbon dioxide)

Part 12Questions About Leisure and Entertainment

  • What’s the last great movie you watched?
  • Do you have any favorite TV shows you’re watching right now?
  • What kind of music do you enjoy?
  • What’s your go-to activity for relaxing after a long day?
  • Do you have any fun weekend plans coming up?
  • What’s your favorite way to spend a day off?
  • Have you picked up any new hobbies recently?
  • What’s the best book you’ve read this year?
  • Do you like to cook? What’s your specialty?
  • What’s your favorite restaurant in town?
  • Which teams do you follow?
  • What’s the most fun vacation you’ve ever taken?
  • Do you have any travel plans for the future?
  • What’s your favorite outdoor activity?
  • What’s your ideal way to spend a rainy day?
  • What’s the best live performance you’ve ever seen?

Part 13Questions About Personal and Professional Achievements

  • What’s the biggest challenge you’ve overcome recently?
  • How did you celebrate your last big win at work?
  • What skill are you trying to improve right now?
  • Can you tell me about a project you’re really proud of?
  • What’s the best piece of career advice you’ve ever gotten?
  • How do you balance your work and personal life?
  • What’s your dream job?
  • How did you choose your current career path?
  • What’s the most valuable lesson you’ve learned at work?
  • What’s the biggest risk you’ve taken professionally?
  • How do you stay motivated at work?
  • What’s your strategy for handling workplace stress?
  • Have you ever changed careers? What was that like?
  • What’s your biggest professional goal for the next year?
  • How do you measure success in your job?

Part 14Questions About Cultural and Current Events

  • Have you been following the developments in [current event]?
  • What do you think about [recent cultural trend]?
  • What’s your favorite news source?
  • How do you think technology is changing our society?
  • What’s your opinion on social media’s impact on culture?
  • What do you think are the biggest challenges facing our generation?
  • How do you think [recent event] will affect the future?
  • What’s your favorite way to learn about different cultures?
  • What’s the most surprising thing you’ve learned about another culture?
  • How do you think our city/country has changed in the last few years?
  • What’s your favorite holiday tradition from your culture?
  • Have you ever lived in a different country? What was that like?
  • What’s the most interesting museum you’ve visited?
  • If you could solve one global problem, what would it be?

Part 15Questions to Ask Kids

Conversations with kids and tweens go better with questions that feel more like a game than an interview. Keep the tone playful and be ready for answers that go in unexpected directions.

  • If you could have any animal as a pet, even a wild one, what would you pick?
  • What’s the best thing that happened at school today?
  • If you could invent a new toy, what would it do?
  • What’s your favorite thing to do with your friends?
  • If you could be any character from a movie or book, who would you be?
  • What’s the silliest joke you know?
  • What do you want to be when you grow up?
  • If you could only eat one snack forever, what would it be?
  • What’s something you’re really proud of that you learned to do this year?
  • What’s your favorite subject in school, and why?
  • If you had a superpower for one day, what would you do with it?
  • What’s the funniest thing that’s ever happened to you?

For older kids and middle schoolers, swap in slightly more open-ended versions, like asking what they’re looking forward to this year instead of just what they want to be when they grow up.

Part 16Questions to Keep a Text or Phone Conversation Going

Texting strips away tone of voice and facial expressions, so a question that sounds friendly in person can read as flat or interrogating on a screen. Keeping things light, curious, and easy to respond to matters more over text than in person.

  • What’s the highlight of your day so far?
  • What are you up to right now?
  • What’s something that made you laugh today?
  • Any fun plans for the weekend?
  • What’s on your playlist lately?
  • What’s for dinner tonight?
  • Have you watched anything good lately?
  • What’s something you’re looking forward to this week?
  • Random thought: would you rather live in a city or the countryside?
  • What’s the weather like where you are right now?

A few habits make texting conversations easier to sustain:

  • Reply within a reasonable window when possible. Long, unexplained gaps can make a conversation feel like it fizzled out, even if that was not the intention.
  • Add a small personal detail before asking your question, rather than sending a question with no context.
  • Send a photo or voice note sometimes instead of only text. It gives the other person more to respond to.
  • If the conversation naturally winds down, it is fine to end it warmly rather than forcing more questions just to keep it alive.
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Part 17Questions for Podcasts, Livestreams, and Group Chats

Public and semi-public conversations, like a podcast interview, a livestream Q&A, or a group chat, call for questions that work for an audience of more than one person at a time.

  • What’s a moment that changed the direction of your career?
  • What’s something you believed early on that you no longer believe?
  • What’s a question you wish more people asked you?
  • What’s the best piece of feedback you’ve ever received?
  • What’s something you’re currently curious about?
  • If everyone in this chat could answer one question honestly, what should it be?
  • What’s a small thing that made your week better?
  • What’s a topic you could talk about for hours?
  • What’s something you’d like this group’s opinion on?

For a recurring “question of the day” post on social media or in a group chat, keep a running list of prompts so you are never starting from scratch. Rotating between funny, reflective, and opinion-based questions keeps the format from feeling repetitive.

Part 18Handling Awkward Silences

Awkward silences can make you feel uncomfortable, but they don’t have to end the conversation. Try these strategies to break the ice:

  1. Ask about their hobbies: “What do you like to do for fun?”
  2. Bring up current events: “Did you hear about the new movie coming out?”
  3. Share a funny story: “The funniest thing happened to me today…”
  4. Ask for their opinion: “What do you think about [topic]?”
  5. Compliment something about them: “I love your shoes! Where did you get them?”
  6. Talk about food: “Have you tried any good restaurants lately?”
  7. Discuss travel: “If you could go anywhere, where would you visit?”
  8. Ask about their job: “What’s the best part of your work?”
  9. Bring up mutual friends: “How do you know [friend’s name]?”
  10. Talk about plans: “Do you have any exciting weekend plans?”

A little silence is okay. It gives you both time to think.

It also helps to notice why the silence happened in the first place. A pause after a deep or emotional answer is different from a pause because the topic ran dry. In the first case, sitting with the silence for a moment often feels more respectful than rushing to fill it. In the second case, reaching for a fresh topic, like the ones above, tends to work better.

Part 19Dealing with Difficult Topics

Sometimes conversations can turn to sensitive subjects:

  1. Show empathy: “That must be really tough for you.”
  2. Acknowledge their feelings: “I can see why you’d feel that way.”
  3. Ask if they want to talk about it: “Do you want to discuss this more?”
  4. Offer support: “Is there anything I can do to help?”
  5. Take a break: “Would you like to take a moment before we continue?”
  6. End the topic respectfully: “I appreciate you sharing that with me.”
  7. Change the subject gently: “On a lighter note, [any open-ended question]?”

A few supportive questions can also help someone feel heard without pushing them to share more than they want to:

  • What would be most helpful for you right now?
  • Do you want advice, or would you rather I just listen?
  • How are you holding up with everything?
  • Is there anything specific weighing on you that you’d like to talk through?
  • What’s been the hardest part of this for you?

Frequently Asked Questions

What are the best questions to ask to keep a conversation going?

The best questions are usually open-ended and connected to something the other person just said. Starting with a broad topic, like work, hobbies, or weekend plans, and then following up based on their answer tends to work better than jumping between unrelated questions from a list.

How do you keep a conversation going over text?

Keep messages short, add a small personal detail before your question, and avoid sending several questions in a row. Since texting lacks tone of voice, lighter and more casual questions tend to land better than heavy or serious ones.

What is a good icebreaker question?

A good icebreaker is easy to answer, has no wrong answer, and gives the other person room to add personality to their response. Questions like “What’s the best thing that’s happened to you this week?” or “What’s a small thing that made you smile recently?” tend to work well because they are low-pressure but still personal.

How many questions should you ask before it starts to feel like an interrogation?

There is no fixed number, but if you notice you have asked several questions in a row without sharing anything about yourself, it is a good time to add a comment or story of your own before asking the next one. Watching for short, one-word answers is also a sign to slow down and shift the tone.

What do you do if someone keeps giving one-word answers?

Try switching from closed questions to open-ended ones, and consider whether the topic itself is the problem. Sometimes a change of subject, or simply sharing something about yourself first, gives the other person more to respond to.

What are good questions to ask a girl you like?

Questions that show curiosity about her personality, sense of humor, and interests tend to work better than generic or overly rehearsed lines. Asking about a favorite memory, what she is looking forward to, or what makes her laugh often opens up a more natural exchange than asking something purely factual.

What are some funny or silly questions to ask friends when you’re bored?

Hypothetical and would-you-rather style questions are reliable for this. Questions like “Would you rather fight one horse-sized duck or a hundred duck-sized horses?” or “What’s the dumbest way you’ve ever gotten injured?” tend to spark laughter and follow-up stories.

What is the “36 questions” method for getting close to someone?

It refers to a set of questions developed by researchers studying closeness, designed to be asked in order from light to increasingly personal. Couples or new acquaintances take turns answering each one, gradually building intimacy through mutual vulnerability. You do not need the full list to benefit from the idea. Starting light and moving toward deeper topics over the course of a conversation works well on its own.

What are good conversation topics for a group chat?

Questions with a clear, easy entry point work best in groups, since everyone can jump in without needing much context. Opinion-based prompts, “this or that” questions, and light hypotheticals tend to get more responses than personal or deep questions in a group setting.

How do you keep a conversation going with someone you just met?

Lean on safe, broad topics first, like how you both know the host of an event, what brought them to the gathering, or what they do for work. Once you find a topic they seem genuinely interested in, follow up with more specific questions about that subject.

What are some conversation starters for kids?

Playful, imaginative questions work best with kids, since they enjoy inventing scenarios more than answering factual questions. Asking what superpower they would want, what animal they would choose as a pet, or what the best part of their day was tends to get an enthusiastic response.

What’s a good “question of the day” for work or school?

Light, low-pressure prompts work well for recurring check-ins. Questions about small wins, weekend plans, favorite meals, or something to look forward to give everyone an easy way to participate without feeling put on the spot.

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