Fun Questions to Ask Strangers

Fun Questions To Ask a Stranger

Talking to strangers can be one of the hardest things to do, if you’re introverted or unsure of yourself. Thinking of a decent ice-breaker that might interest a stranger, but not appear to be a come-on, is hard to do when you’re sitting on a bus or in the waiting room at some office. Even when you’re at a party where everyone presumably arrived to have a good time and get to know other people better, asking fun questions to a stranger can seem, well, strange.

Sometimes, though, off-the-wall questions break the ice and get a real reaction from a person, where asking about the news, weather or sports is likely to get the same canned answers they would give anyone else. It’s not such a bad thing to embrace the strangeness of a talk with someone you know nothing about. In fact, getting something personal (but not too personal) out of them is a good way to introduce yourself. At the very least, your new acqaintance won’t forget the first question you ever asked them.

So here are fun questions to ask a stranger you meet in the everyday course of your life. Try to ask these questions as if you’re talking to an old friend or family member. That will throw them off.

  • Do I look fat?
  • What did you do last night?
  • Why don’t we elope?
  • When is the last time you called in sick?
  • Have you had your 15 minutes yet?
  • Didn’t your mom ever tell you not to talk to strangers?
  • What are you on?
  • What’s your favorite time of day?
  • What was your New Year’s resolution this year? How long did it take you to break it?
  • What is your biggest regret?
  • What’s the last thing you ate?
  • What’s the last impulse buy you made?
  • What was the last thing that made you feel like an idiot?
  • What did you get for Christmas last year?
  • Why don’t we take the day off and go to the beach?
  • What would come up on a Google search of your name?
  • When and where was your best vacation?
  • (Pointing at your shirt top) Is this my color?
  • What’s the strangest dream you’ve ever had?
  • What’s the last event you dressed up for?
  • What color hair do you prefer in the opposite sex?
  • How many times a week do you shower?
  • What’s the most expensive thing you have on right now?
  • Who is your role model?
  • If you could only wear one color for the rest of your life, which color would it be?
  • Why don’t the make mouse-flavored cat food?
  • What’s your favorite memory?
  • Do bald people use soap or shampoo on their head?
  • What are your nicknames?
  • What’s the plural form of mongoose?
  • What’s the funniest thing you’ve heard today?
  • What’s the funniest thing you’ve said today?
  • Why do you press harder on the remote when you know it’s the battery that’s going dead?
  • What’s the color of your toothbrush?
  • Why do we answer the phone with “Hello” when the better answer would be “Who is this”?
  • If quizzes are quizzical then what are tests?
  • What’s your ringtone?
  • So do you have a crush on someone right now?
  • What are your nervous habits?
  • Do you like sushi?
  • When was the last time you sat and looked at the stars?
  • Do you ever spit?
  • How do you feel about long distance relationships?
  • Where are your ticklish spots?
  • How often do you cook your own food?
  • Do you have any pets? What are their names?
  • So what brand of underwear are you wearing?
  • When was the last time you drank a bottle of alcohol by yourself?
  • Have you ever regretted loving someone?
  • When was the last time you were super happy?
  • On a scale of 1 to 10, how happy are you with your life right now?
  • Do you prefer the sunrise or sunset?
  • Have you ever been in a car accident?
  • What kind of fashion sense attracts you?
  • What’s your favorite hair style on a woman?
  • Are you afraid to ask people out on dates?
  • What’s the usual age range you look at for dates?
  • What are the positive parts of being single?
  • What are the negative parts of being single?
  • How well do you handle rejection?
  • What’s the longest relationship you’ve ever been in?
  • How do you handle disagreements?
  • Would you prefer to have 5 acquaintances or 1 friend?

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