Unconventional Conversation Starters
What’s the pettiest thing you’ve ever done?
Could you beat a younger version of yourself in a race?
What’s the sweatiest you’ve ever been and why?
How do you think elevators could be improved?
What’s something you keep buying even though it’s stupid?
What’s something you still haven’t finished?
Who did you sit next to at your high school graduation?
What free beverage do you ask for on airplanes?
Are shoes fun?
Do you think trees should be a different color?
How many pillows are too many pillows? How many pillows aren’t enough pillows?
What is something you prefer to do alone?
How much time could you consecutively spend at a movie theatre?
When’s the last time you got lost in someone’s house?
How many soaps do you use in your shower?
What product from your hometown is most likely/most known as being a pyramid scheme?
Would you enjoy a cave?
Are you a washer or a dryer?
What letter would you add to your first name?
What letter would you subtract from your last name?
If you use the “paste” function on your phone right now, what do you have copied/pasted?
What’s the worst song lyric?
Do you have to make any returns at a store currently?
What’s something that should be heavier than it is?
Are corn fields scary?
Imagine it’s the last time you’ll ever walk across a bridge in your life.
What bridge do you choose to walk across?
What is a fair price for a glass of lemonade?
Sing a jingle to a TV commercial that you always heard as a kid and still know all of the words to.
Do you hold the elevator door for others?
What’s a karaoke song you would be great at performing, but it’s not popular enough for everyone to know?
How big does a space have to be for you to get lost in it?
Can you name an example of the smallest and largest spaces you’ve gotten lost in before?
What do you do on an airplane?
What would be your prison nickname?
How do you pronounce “Hoyt-Schmerherhorn?”
What game show would you be good on?
What’s the most useless college class you took?
What’s something you do every day that most people don’t?
What obsolete piece of technology do you most identify with?
Name a town or place that you’ve only ever visited once.
What activity would be worse if it had to involve a pie?
What’s something that nobody ever buys from your local bodega?
What do you always look at when you’re at the checkout counter?
Where would you hide in a cemetery?
How many cans of soup would it take to fill the room you are currently in?
Do you have any opinions on anything that only you believe?
Which is worse: watching a sport you know nothing about,
or only watching the second film in a trilogy?
What movie would you want to be in? What movie do you deserve to be in?
What do you always lose? What is something that you’ve never lost?
Which is your favorite tooth?
If you were hosting an event but could only play one song on repeat the entire time,
what song would you play and what kind of event would you host?​​​​​​​
What is your worst Craigslist experience?
If you had a personal assistant, what would be a part of their job description?
What is the last thing you did for the last time?
What is the last music purchase you made?
What celebrity are you most likely to get in a fight with?
What band/musician did you most listen to in college?
What are your three favorite fruits?
What is the weirdest thing about you?
What would your role be if you were in a circus?
What four songs do you associate with each of the seasons?
What is something you grew up with?
What instrument did you play in school band or orchestra?
Describe a moment where you really impressed yourself.
When you have to make a decision, would you rather be given more or fewer choices to choose from?
What is the last thing you forgot to get at the grocery store?
Quickly name the first painting you can think of. Who is the artist?
What fictional character's home do you wish you could to live in?
If cars didn't exist, what would your primary mode of transportation be?
Are you left or right handed?
What is something you hate waiting for?
What is something that you don't really mind waiting for?
What is the tagline for your life?
Would you rather be gifted 500 marbles or 500 seashells?
It's 2am, and you walk into a bodega. What are you there to buy?
What is your favorite song from a musical or movie?
If you were a cake, what kind of cake would you be?
What would it take for you to stay awake for 24 hours straight?
Describe the best story you have about a time when you made a last-minute decision.
Have you ever hung out with your current neighbors?
Which of your social media accounts or online profiles do you think represents you the best?
What internet video do you occasionally or suddenly remember, and then plays on repeat in your mind?
What is your infamous breakup song?
What movie do you watch when you're sad?
Have you ever won an award?
What makes a "good morning" truly a good morning?
What was your hardest or easiest teenage year?
What do your pajamas look like?
Who was your childhood celebrity crush?
Imagine you have to bring something you've acquired this year for a "show and tell."
What item do you choose?
Describe the best formal event that you've ever attended.
What was the best morning that you've ever had?
What is the dumbest question someone has ever asked you?
What is your favorite thing to look at?
What have you done that could earn you a key to the city?
How many meals have you cooked in your current apartment?
What year of your life was most different from your everyday life?
Do you collect anything?
How do your friends describe you?
What do you daydream about?
Name a song you'd expect to be playing inside a convenience store.
Do you believe in ghosts?
What's your favorite sound?
What's something that should be free?
What is your favorite shape?
Would you rather wear tight or loose clothing?
What's the best or worst thing that you've ever had to wait 30 minutes for?
What is the tallest floor of a building that you've explored?
What was your SAT essay question?
What's been your favorite year of your life so far?