100 Best Conversation Starters for Deep or Fun Conversations

It’s the social situation we all dread: you’re in a meeting, doing your best to mingle, and saying hello to someone you don’t know. You introduce yourself…then comes the long and awkward pause. Neither of you have any idea what he’s going to say next. This is where a good catch phrase can come to the rescue. In fact, you might even want to stock up on a few. After all, whether you’re relaxing at a neighbor’s BBQ in the backyardnetwork at a business event or spend time with family picnicchances are you need to have a little chat with someone at some point.

While chatting can be a tough proposition for many of us (especially introverts: we feel your pain!), it doesn’t have to be, thanks to the following icebreakers. Very simple conversation starters like “What is your favorite hobby?” to fun questions, such as “What’s your best dance move?” these questions could help spark an engaging and lively discussion or maybe even a one-on-one. What – hey, you never know – might just end up blossoming into a new friendshipworking partnership, or romantic relationship. Looking for more ways to engage and keep the conversation going? Check out our hilarious and funny jokes to make your friends and family laugh.

Simple Conversation Starters

a front view of two beautiful middle aged women enjoying coffee together in a cafe, they are sitting at a table and laughing togetherpinterest icon


  • What’s the number one item on your bucket list?
  • What is the best book you have ever read?
  • If you could live anywhere in the world, where would it be?
  • What’s your favorite comfort food?
  • What pet peeve drives you the craziest?
  • What is the last movie you saw at the cinema?
  • Which website do you spend the most time sucking?
  • What is your favorite hobby ?
  • If you could time travel, what period would you visit?
  • What’s the best concert you’ve seen?
  • Are you in favor of any sports teams in particular?
  • What’s the worst job you’ve had?
  • What do you like more: dogs or cats?
  • Are you a morning type or do you like to stay up late?
  • What five albums would you take to a desert island?
  • What would you do with that money if you won the lottery?
  • Do you like your job?
  • Have you ever met someone famous?
  • How did you and your partner meet?
  • What apps do you use the most?

In-depth conversation starters

couple of friends sitting, chatting and catching up together in a cafepinterest icon

Hinterhaus Productions

  • Who is your greatest role model?
  • What is your best childhood memory?
  • Where do you want to be in 10 years?
  • What is your definition of success?
  • What is your personal motto?
  • What day would you choose to live in your life?
  • What advice would you give to yourself at 18?
  • Is there a lesson you had to learn the hard way?
  • What did you want to be when you grew up?
  • What is your best quality?
  • What would you most like to change about yourself if you could?
  • Who is the most important person to you?
  • What are people surprised to learn about you?
  • What’s the hardest thing you’ve ever done?
  • What is your greatest pride?
  • Do you have any regrets?
  • When are you happiest?
  • What are you most afraid of?
  • What opinion did you have that has changed over time?
  • Where do you find inspiration?

Funny Conversation Starters

happy male and female friends enjoying champagne while talking at home during Christmas celebrationpinterest icon

Klaus Vedfelt

  • When was the last time you laughed so hard you almost got wet?
  • What’s your favorite song to sing in the shower?
  • If you could have one superpower, what would it be?
  • What’s the worst line you’ve ever heard?
  • What’s the best joke you know?
  • If you worked in a circus, what would your job be?
  • What’s your best dance move?
  • What was your most embarrassing moment?
  • What’s your weirdest quirk?
  • If you could trade your life with any celebrity, who would it be?
  • What’s the weirdest food in your fridge?
  • Do you think aliens exist on other planets?
  • What’s your weirdest guilty pleasure?
  • What is the scene from the movie that never fails to make you laugh out loud?
  • What’s the most embarrassing thing that’s ever happened to you?
  • If you could invent a holiday, what would it celebrate?
  • Do you have a hidden talent?
  • What’s the dumbest thing you’ve ever searched on Google?
  • What old age habits do you have?
  • What would be the title of your memoir?

Network conversation starters

two colleagues work together on their laptops during a meeting in a cafepinterest icon

Flagship films

  • What is your professional goal for this year?
  • Why did you choose this career?
  • What is one thing you learned this month?
  • What was your first job?
  • Do you listen to anything while you work?
  • What big challenge have you faced recently?
  • How do you relax after work?
  • What do you like most about your job?
  • Do you have a career model?
  • If you could work remotely from anywhere, where would it be?
  • What part of your job do you wish you could automate?
  • What are you most excited about that will happen in the next term?
  • Where is the best place you have traveled for work?
  • Have you tried a standing desk?
  • What’s the craziest thing you’ve ever heard in a meeting?
  • Big plans for the weekend?
  • What project are you working on?
  • If you could work in another department for a day, what would you do?
  • What do you think is the most important skill to have in your job?
  • What would you be doing now if you weren’t doing this job?

Dating Conversation Starters

couple toasting wine glasses in restaurantpinterest icon

The Good Squad

  • What qualities are you looking for in a partner ?
  • What would I never guess about you?
  • Which fictional character would you like to date?
  • What do you like best on a first date?
  • Are you more extroverted or introverted?
  • What excites you the most?
  • What three words would you use to describe yourself?
  • What’s the worst date you’ve ever had?
  • If you had a theme song, what would it be?
  • Who was your first kiss?
  • What’s your perfect day?
  • If money weren’t a problem, what would you do with your life?
  • What is the strangest thing you find attractive in a person?
  • Do you believe in love at first sight?
  • What caught your interest in me?
  • What are the deciding factors for you?
  • What takes your breath away?
  • If you took me to visit your hometown, where would we go?
  • How do you imagine your life in ten years?
  • What is your love language?
Portrait of Jill Gleeson

Jill Gleeson is a travel journalist and memoirist based in Appalachia, western Pennsylvania who has written for websites and publications including Good Housekeeping, Woman’s Day, Country Living, Washingtonian, Gothamist, Canadian Traveler and EDGE Media Network. Jill is the travel writer for Enchanted Living. Learn more about his journey at gleesonreboots.com.


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