225 Conversation Starters for Any Situation

225 Conversation Starters for Any Situation

What’s your go-to conversation starter?  

Navigating dinner parties and gatherings can be a bit tricky, especially when you’re among unfamiliar faces. These conversation icebreakers are your secret weapon! As the holiday season approaches, these gems will be your trusty companions at every party and event. And, if you’re the ultimate host looking to ensure your guests have a blast, consider crafting a conversation jar to keep the chatter flowing smoothly. Or, perhaps, kickstart the evening by sharing a glass of wine while bonding over your personalized household items. 


Whether you’re eager to connect with someone new or simply keen on rediscovering an old friend, unconventional questions are your ticket to breaking the ice and uncovering exciting new insights! 

How to Create a Conversation Jar

A conversation jar can help you get beyond small talk and start a fun, unusual conversation! It assures that you have a few conversation starters in your back pocket. To create a conversation jar:

  1. Download and print the conversation starters below.
  2. Cut them out.
  3. Place in jar or cup.
  4. Get talking!

Funny Conversation Starters

These conversations starters are good for people young and old! They are sure to spark some creative answers, get the group laughing and bring back some hilarious memories.

  • If you were in a circus, which character would you be?
  • What is the worst advice you have given?
  • What is one thing you should never say at a wedding?
  • What is the worst pickup line you have ever heard?
  • If you could only store one type of food in your pocket, what would you carry?
  • What is the worst present you have ever received and why?
  • If you were a farm animal, which would you be and why?
  • What is the worst first date you have ever been on?
  • Have you ever stalked someone on social media?
  • What is the best part about taking a selfie?
  • What is your favorite celebrity scandal?
  • If you could do anything illegal without getting caught, what would you do?
  • What is the weirdest food combination you’ve ever tried?
  • Did you have an imaginary friend? What was his/her name?
  • Have you ever had a dream where everyone was in their underwear?
  • Who’s your favorite comedian?
  • Have you ever been on a blind date?

Conversation Starters For Kids

As we all know, kids have big imaginations. Why not encourage them with these kid-friendly conversation starters? They’re sure to respond with unique (and surprisingly insightful) answers.

  • If you could make up a school subject, what would it be?
  • What is your very favorite letter of the alphabet? Why?
  • If someone gave you 20 dollars, what would you buy with it?
  • If you had a chance to eat dessert for breakfast every day, what dessert would you choose?
  • What is the first thing you think about when you wake up in the morning?
  • Which animal at the zoo do you like best?
  • If your friend is sad, what do you do to make them feel better?
  • If you had the opportunity to invent a new ice cream flavor, what would it be?
  • What is the silliest thing someone has ever said to you?
  • What’s your idea of a perfect playground?
  • What’s your favorite word?
  • Would you switch roles with your parent if you had the chance?
  • When was the last time you used the words “thank you”?
  • If you had a robot for the entire day, what would you ask it to do?
  • Do you prefer cold weather or hot weather?
  • If you never had to eat one vegetable, which would it be?
  • What was the last thing that made you smile?
  • What is your favorite part about school? Your least favorite?
  • How do you make friends?
  • Who makes you laugh the most?

Conversation Starters for Teens

Sometimes teens can be difficult to talk to. If you have trouble relating to a teen in your life, try one of these conversation starters to get them talking about what excites them most.

  • What do you most like about yourself?
  • What hurts your feelings?
  • If you could be famous, would you want to? Why?
  • Who is a celebrity you admire?
  • What made you laugh at school today?
  • Did anything make you upset today?
  • If you could have more friends, would you?
  • What do you like most about your friends?
  • Is there anyone at school you’d like to know better?
  • Have you ever lost a friend? Why?
  • Where do you want to be ten years from now?
  • If you had $100, what would you spend it on?
  • Is there something you’d want to do as a family?
  • If you were to choose one way to be disciplined, what would it be?
  • What do you think are the best traits for a person to have?
  • Would you ever get a tattoo? What would it be?
  • What do you think is a good age to start dating?
  • Why do you think popular kids are popular?
  • If you could go anywhere in the world, where would you choose and why?
  • What is something you wish you could do everyday?

Deep Conversation Starters

Tired of talking about the weather, latest sports game, or what you’re up to at work? Get real with these deep conversation starters. Just make sure you’re ready for a serious conversation.

  • What are the top three things on your bucket list?
  • How do you think you will die?
  • What has been the lowest point of your life?
  • If you could ask for a miracle, what would it be?
  • Where do you see yourself in five years?
  • What is the biggest risk you’ve ever taken?
  • What would your ideal life look like?
  • If someone gave you an envelope with your death date inside of it, would you open it?
  • When have you been the most happy?
  • Do you know anyone who is living their life to the fullest?
  • What is your idea of the perfect day?
  • Who has been the most influential person in your life and why?
  • What book had a big influence on you?
  • Do you think your priorities have changed since you were younger?
  • What is the most memorable lesson you learned from your parents?
  • What does success mean to you?
  • What is the most difficult thing you’ve ever done?
  • What scares you most about your future?
  • What keeps you up at night?

Conversation Starters For Couples

You may feel like you know everything about your significant other, but it’s easy to get in a routine and have similar conversations every day. Spice it up with these meaningful questions.

  • What do you think people need to know about each other before they get married?
  • What makes you very sentimental?
  • What do I do that makes you smile?
  • What is the best or worst trait you inherited from your parents?
  • What is your funniest memory of our dates?
  • Who was your first crush and why?
  • What three things do you want to be remembered for?
  • Is there a dream you’ve always had?
  • What is something you’ve always wanted to do, but are scared to?
  • What gives you butterflies?
  • What do you consider most romantic?
  • What motivates you most in life?
  • What things do you consider to be relationship deal breakers?
  • Do you think arguing is part of a relationship?
  • If we were to raise children, what are the most important things you would want them to learn?
  • How would you describe our relationship?
  • How would your partner describe you?
  • Do you consider yourself a spiritual person? How?
  • If you made a bucket list for us, what would you add to it?
  • How has our relationship changed since we started dating?
  • What do I do that comforts you the most?
  • In what ways are you most similar to me?
  • What makes you feel discouraged?
  • What is a significant event that has changed you?
  • If your life was a movie, which celebrity would play you?

First Date Conversation Starters

Let’s face it, first dates can be awkward. Start off on the right foot with these first date conversation starters. They’ll help you get to know the person and find out your common interests.

  • What’s something not many people know about you?
  • What are you most passionate about?
  • What makes you laugh out loud?
  • What was your favorite thing to do as a kid?
  • Who do you text the most?
  • What do you like to cook the most?
  • What’s your favorite TV show?
  • What is your favorite book?
  • Who is most influential in your life?
  • What was your best friend’s name growing up?
  • How do you spend your mornings?
  • What’s your all-time favorite band?
  • What’s your dream job?
  • What did you study?
  • What did you want to be growing up?
  • What is the best pickup line you’ve ever used? Heard?
  • Do you have any nicknames?
  • What talent do you wish you had?
  • Where do you see yourself living when you retire?
  • What is your favorite weekend activity?
  • Do you have any pet peeves?
  • Who was your favorite teacher and why?
  • What makes you most uncomfortable about dating?
  • What is your favorite place in the entire world?

Dinner Party Conversation Starters

If you’re at a gathering with acquaintances, it can be hard to settle on a topic that everyone can relate and contribute to. Try one of these conversation starters to find similar interests!

  • If you could have dinner with anyone living or not, who would it be?
  • Are you a cat person or a dog person?
  • What is the silliest thing you’ve posted online?
  • What was your worst wardrobe mistake?
  • What is the best restaurant you’ve been to?
  • What is your favorite kitchen smell?
  • When you die, what do you want to be reincarnated as?
  • What is your favorite guilty pleasure TV show?
  • What was your worst “foot in mouth” moment?
  • Who would you swap lives with for a day?
  • If you could live anywhere in the world, where would it be?
  • What is the strangest gift you have ever received?
  • What is the funniest gift you have ever given?
  • What are three fun facts about yourself?
  • What’s the best compliment you’ve ever received?
  • Would you rather be invisible or have X-ray vision?
  • If you could only save one item from a house fire, what would it be?
  • What is the one food you could eat for the rest of your life?
  • How do you know (person hosting dinner)?
  • If you won the lottery, what would be your first big splurge?
  • What’s one movie you could watch over and over?
  • Where’s the most exotic place you’ve ever been?
  • If you could have picked your own name, what would it be?

Conversation Starters For A Family Gathering

Sometimes it can be difficult to figure out what to talk about at extended family gatherings, especially if you haven’t seen family members for awhile. These conversation starters are family-friendly and are sure to engage everyone from children to grandparents.

  • What time period would you travel to?
  • What is one thing you can’t live without?
  • What is your least favorite chore?
  • What is your earliest memory?
  • Who are you most thankful for and why?
  • Where do you want to go on the next family vacation?
  • What’s the nicest thing a family member has ever done for you?
  • What was the biggest punishment you’ve ever received?
  • If you could describe yourself in three words, what would they be?
  • What would be the first thing you would do if you traded places with your family member?
  • What instrument would you like to play?
  • If you could get all your family members to donate to a charity, what would it be and why?
  • Would you want to live on a boat, a mountain or an island?
  • What makes you most proud?
  • What three things are you most grateful for?
  • Who do you count on the most for help?
  • What would make you (if parent) most upset? A tattoo, a nose ring or a bad boyfriend/girlfriend?
  • What would be your ideal day?
  • What makes you the happiest?
  • If you could spend an entire day with a family member, who would it be and why?
  • If you could be an animal, what would it be and why?
  • If you could be any age, what age would you choose?
  • What’s one thing you’ve won and how did you win it?
  • What did you think was the most challenging part of being a kid?
  • When is the last time you laughed so hard that you cried?

Networking Conversation Starters

After you’ve asked “What do you do?” where should the conversation go from there? These questions will open up conversations beyond just discussing your job title.

  • How did you hear about this event?
  • What was the first job you ever had?
  • What’s a good place to eat around here?
  • What are you reading right now?
  • How was your commute here?
  • What fun plans do you have for the weekend?
  • What cool conferences have you attended?
  • How long have you been at your current job?
  • What’s the most fun project you’ve ever worked on?
  • Did you hear about (insert latest news topic)?
  • Where do you see yourself in five years?
  • Have you ever won an award?
  • How old were you when you had your first job?

Conversation Starters For A Casual Get-Together

A casual get-together with friends is a good place to ask quirky questions. Find out fun information about your friends and acquaintances that you may have never known otherwise!

  • How long can you go without checking your phone?
  • Have you ever really kept a New Year’s resolution?
  • What bad habits do you wish you could stop?
  • Do you have a morning ritual?
  • Have you ever been stalked on social media?
  • Can you tell when someone is lying?
  • Are you a jealous person?
  • Do you prefer polaroid or digital cameras?
  • If someone offered to tell you your future, would you accept it?
  • Who’s your biggest hero?
  • Have you ever stolen anything?
  • If you were to remove one social media app from your phone, which would it be and why?
  • If you could have tea with a fictional character, who would that be?
  • What is your most embarrassing moment?
  • If you were on death row, what would your last meal be?
  • If you could sit down with your 13-year old self, what would you say?
  • If you could only pack one thing for a trip (besides clothing) what would it be?
  • What makes you really angry?
  • What is your spirit animal?
  • What would be the title of your memoire?
  • What’s your guilty pleasure?
  • What would your theme song be if you had your own show?
  • What bores you?
  • What would you do if you were home alone and the power went out?
  • What’s the weirdest dream you’ve ever had?
  • If your plane was going down, who would you would call?
  • What would your rock band group be called?

Conversation Starters At A Bar

Whether you’re trying to meet a new friend or special someone, these conversation starters are a great way to break the ice! If you’re new to the area, they’ll also help you learn more about all the best spots to visit.

  • What drink do you suggest I get?
  • How do you get to X place from here?
  • Where is a good place to get food around here?
  • I’m NAME, what’s your name?
  • Are you having a good time?
  • Batman or Superman, who would win?
  • This song is so overplayed, I’d rather hear X. How about you?
  • What’s the worst thing one can say on a first date?
  • What made you laugh this week?
  • Are you having a good evening?
  • What do you think of this place?


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