145 Best Conversation Starters to Skip the Small Talk

Wondering how to start a conversation? I could say simply that you aren’t alone in wondering. Or I could break the fourth wall a little. Humor me the latter.

As a writer in the digital age with access to things like tools showing how many people search for certain topics on Google each month — which, yes, is as fun and voyeuristic as it sounds — there are numbers (receipts, even!) to prove you aren’t alone here. As of this writing, 135,000 people are plugging “conversation starters” into Google every month. And that’s just the people searching for conversation starters in English! The same number are googling “discussion starters,” and about 32,000 people monthly are looking up “conversation ideas.”

All of which is to say, if you’re less than 100-percent confident in your capacity for initiating convos, join the club. Whether it’s taking a new class, starting a job, making new friends, or going on a first date, we’re all regularly in situations where we have to figure out how to break the ice with convo starters or otherwise get comfortable with mildly awkward silence. Since chatting and getting to know new people is the more fun option for many of us, that makes conversation starters a good thing to have in your back pocket.

No matter the social situation you’re heading into, having a few go-to convo starters to pull from can take away some anxiety and help you get to know new people while feeling relatively relaxed about it. And when we’re relaxed is when we can really let conversations flow and organically take us any which way they please. That’s the goal, after all!

So before you declare an air of aloofness your default in new social settings, brush up on some of our most trusted conversation starters ranging from the deep to the decidedly unserious. Below, you’ll find:

Fun Conversation Starters for Friends
Deep Conversation Starters
Silly Conversation Starters
Conversation Starters with a Crush

Fun Conversation Starters for Friends

If you could swap lives with any fictional character for a day, who would it be?
What’s the weirdest food combo you actually love?
If our friend group (or class, or group of coworkers) had a theme song, what would it be?
What’s the most spontaneous thing you’ve ever done?
If you had to relive one day of your life on repeat, which would you choose?
What’s a guilty pleasure movie or TV show you refuse to stop watching?
If you could instantly master any skill, what would it be?
What’s a song or artist that instantly puts you in a good mood?
If you could turn any mundane task into an Olympic sport, what would you dominate?
If you could only eat one cuisine for the rest of your life, which one would it be?
What’s the funniest autocorrect fail you’ve experienced?
If you could design your dream vacation, what would it look like?
What’s the best compliment you’ve ever received?
If you had an anthem that played when you walked into a room, what would it be?
If you could have any animal as a pet (real or mythical), what would it be?
What’s your go-to karaoke song?
If you could be best friends with any celebrity, who would it be?
What’s your favorite random fact?
If we started a business together, what kind of business would it be?
What’s the most ridiculous fashion trend you’ve ever followed?
If your life was turned into a sitcom, what would it be called?
If you could only speak in quotes from one movie or TV show, which would it be?
What’s the most creative excuse you’ve ever used?
What’s your ultimate dream concert lineup?
If you got to choose your own name, what would it be?
If you could time travel to any moment in history, where would you go?
What’s the most fun road trip you’ve ever been on?
What was the first movie you remember seeing in theaters?
If you had to live inside the world of a video game, which would it be?
What’s the weirdest app on your phone right now?
Do you have any totally irrational fears?
What’s your Roman Empire?
Have you ever had your fortune told?
If you could be a contestant on any game show, which one would you pick?
If you could create a holiday, what would it be and how would people celebrate?
What’s your most infamous “oops” moment?
Do you buy into astrology?
If you were a ghost, how would you haunt people?
What’s the best museum you’ve ever been to?
What’s something weird you definitely believed as a child?
Do you have any superstitions?
What’s your favorite thing you own and why?
What’s your favorite movie of all time?

Deep Conversation Starters

What’s one experience that completely changed your perspective on life?
How do you define success?
What’s something you’re currently trying to get better at?
What’s a moment in your life that you’ll never forget?
How do you handle failure?
What’s something you regret not doing?
What’s your biggest fear about the future?
If money wasn’t an issue, what would you be doing right now?
How do you want to be remembered?
What’s the hardest lesson you’ve ever learned?
What do you value most in a friendship?
If you had one year left to live, how would you spend it?
Do you believe people can change?
What’s one habit you’re trying to break or build?
What’s the kindest thing someone has ever done for you?
Have you ever had an experience you couldn’t explain? (Yes, we’re talking about the paranormal.)
What motivates you to keep going when things get tough?
When you picture yourself feeling perfectly happy, what do you picture?
What’s the biggest risk you’ve ever taken?
How do you measure personal growth in your own life?
If you had unlimited time, what hobby would you pick up?
What do you think is your greatest strength?
What’s your conflict management style?
Have you ever had a moment of complete clarity?
What’s one thing you’ve always wanted to do but haven’t?
How do you know when you truly trust someone?
What’s one belief you used to hold but no longer do?
Do you believe in fate or free will?
What’s your love language?
Do you believe in soulmates?
Is it ever ok to lie to someone?
If you could apologize to someone from your past, who would it be and why?
What’s the hardest decision you’ve ever had to make?
How do you find purpose in your life?
What’s something you’re really proud of?
Which are you choosing: going back to tell your past self one thing, or skipping ahead to tell your future self one thing?
What’s the most bizarre coincidence you’ve ever experienced?
Do you most often follow your heart or your head?
Do you trust people easily?
Do you believe in life-long monogamy?
If you could live anywhere in the world, where would it be?
Do you believe in an afterlife?
What are you excited about right now?

Silly Conversation Starters

What’s the weirdest thing in your Google search history right now?
What’s the most ridiculous argument you’ve ever been in?
What’s the worst haircut you’ve ever had?
If you had to survive a zombie apocalypse with three celebrities, who would they be?
What’s the funniest misheard song lyric you’ve ever sung?
If your pet could talk, what do you think they’d say about you?
What’s the most embarrassing thing that’s ever happened to you in public?
What’s a word you always struggle to pronounce?
What’s the worst text message you’ve ever accidentally sent?
If you had to wear a Halloween costume every day for a year, what would it be?
What’s the most bizarre or unexpected talent you have?
If you could rename yourself something completely ridiculous, what would it be?
What’s the strangest thing you’ve ever done on impulse?
If your life was a sitcom, what would be the title of the current episode?
What’s a joke that always makes you laugh?
If you had to switch places with a cartoon character, who would it be?
What’s the worst excuse you’ve ever used to get out of something?
If you had a catchphrase, what would it be?
What’s the funniest WiFi name you’ve ever seen?
If your life had a blooper reel, what moments or experiences are you putting on it?
What’s the strangest way you’ve ever injured yourself?
What’s a conspiracy theory that you think is so ridiculous it might actually be true?
What’s the funniest gift you’ve ever received?
If you could make one not-actually-serious thing illegal, what would it be?
What’s the most ridiculous name you’ve ever given a pet?
What’s the funniest thing a kid has ever said to you?
What’s the most ridiculous piece of trivia you actually remember?
What’s a deeply random thing you’d actually love to have as a tattoo?

Conversation Starters with a Crush

What’s the most fun you’ve ever had on a date?
What’s the worst date you’ve ever been on?
What’s your ideal way to spend a lazy Sunday?
What’s the worst pickup line you’ve ever heard or used?
What are the qualities that attract you most in a love interest?
Who was your very first crush?
What does your name mean, and why was it given to you?
How do you think your friends describe you?
What’s a little thing someone can do that instantly makes them more attractive?
If I asked you to plan our perfect first date, what would we do?
What’s something you’d love to do, but it would be way more fun with the right person?
If we spent an entire day together with no phones or internet, what would we do?
If you had to compare me to a fictional character, who would I be?
Are there any songs that make you think of me?
What’s one thing you think people don’t compliment you enough on?
What do you think the most romantic song is?
If we were the last two people on Earth, what’s the first thing we’d do?
If I texted you right now saying “let’s do something crazy,” what’s the first thing that comes to mind?
What’s a random thing about you that would surprise me?
What’s something you think we’d get really competitive over?
What’s one thing that’s completely overrated when it comes to dating?
If I dared you to send me the last thing you screenshotted, would you?
If you could steal one quality from me, what would it be?
What movie couple would we be?
If I asked you to teach me something, what would you pick?
If we had to come up with a couple’s Halloween costume, what would it be?
If we got lost together on purpose, where do you think we’d end up?
What’s something you’d love to experience with me for the first time?
What’s something about me that makes you curious?
What’s one thing you think we’d be surprisingly good at doing together?
Want to play Never Have I Ever (spicy edition)?