• If you could only eat one thing for the rest of your life, what would it be?
• What’s the weirdest thing you’ve ever eaten?
• What’s your go-to comfort food?
• Are there any foods that you absolutely would not eat?
• What are the best cheap eats around here?
• D...

• What’s the best “hidden gem” around here?
• If you could fly anywhere for free, where would you go?
• What’s the coolest road trip you’ve ever been on?
• Where’s the last place you traveled? What did you do there?
• Do you prefer action-packed vacations or relaxing on...

• If you weren’t working here, what would you probably be doing right now?
• How did you become a [job title]?
• What’s the craziest thing a boss has ever asked you to do?
• If you were guaranteed to be successful, what job would you want?
• What was your first job? Did...

If you often find yourself participating in small talk about topics you have no interest in or have already discussed to exhaustion, the solution may be asking people unexpected, thought-provoking questions that can’t be answered with a simple yes or no.

• If you were in charge of picking the eighth wonder of the world, what would you choose?
• What do you wish you had placed in a time capsule 15 years ago?
• What’s the strangest compliment you’ve ever gotten?
• If you could teach a college course on any subject you want, wha...

• Where did you live before this? What are the biggest differences you see?
• What did you think you were going to be growing up?
• Do you have any hidden talents or surprising hobbies?
• What’s the most unbelievable thing that’s ever happened to you?
• Who’s the most i...