First Date Questions

Have you ever struggled to keep the conversations fun & interesting with your new crush?

These First Date Questions will help you explore getting to know each other better whilst keeping the conversations positive and exciting.

Icebreakers & Imaginative Scenarios

• If you had to survive with only 3 items in Alaska, what would you bring with you?
• If you lost everything and had to start over, what would be most important to you? How would you do it?
• If you could only eat one food for the rest of your life, what would it be?
• If you could invite anyone in the world to dinner, who would it be?
• Would you like to be famous? In what way?
• Do you have any viral comments on Instagram? If so, what were they?

Daily Life & Routines

• What would constitute a “perfect day” for you?
• Before a telephone call, do you ever rehearse what you’re going to say?
• When was the last time you sang to yourself or to somebody else?

Personal Growth & Ambitions

• If you were able to live to 90 and maintain the mind or body of a 60-year-old for the last 30 years, which would you choose?
• If you could wake up tomorrow having obtained one quality or skill, what would it be?
• Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

Memories & Life Story

• Take four minutes to tell your life story in as much detail as possible.
• What is your most treasured memory?
• What is your most terrible memory?

Connection & Mutual Appreciation

• Name three things that we seem to have in common.
• What does friendship mean to you?
• What role do love and affection play in your life?
• Alternate telling one another a positive character trait about them.

Big Questions & Future

• If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
• Do you have a secret hunch about how you will die?

Fun & Lighthearted Scenarios

• If you could instantly become an expert in one random skill, what would you choose?
• What is the most ridiculous rule or law you would enforce if you were ruler of the world for one day?
• If you had to enter a reality TV show, which one do you think you’d actually win?
• If your life was a movie, what genre would it be and who would play you?
• What is the worst advice you’ve ever actually taken?

Pop Culture & Hot Takes

• What is a movie or TV show everyone seems to love that you secretly can’t stand?
• What song are you guaranteed to sing along to every time it comes on?
• What is your most controversial opinion on something totally minor (e.g., food, household habits)?
• What was your very first concert, and what was your favorite concert of all time?
• What is a trend or fashion phase you participated in that you now deeply regret?

Travel & Adventure

• If we were forced to go on a spontaneous trip tomorrow with no plan, where would you want to land?
• What is the most bizarre or unusual place you’ve ever visited?
• Are you a “relax on a beach” traveler or an “action-packed itinerary” traveler?
• What’s the strange item you always pack when you travel, just in case?
• If you could spend a month living anywhere in the world rent-free, where would it be?

Habits, Quirks & Preferences

• What’s your ultimate comfort food when you’ve had a tough day?
• Are you a night owl, an early bird, or just perpetually tired?
• What is a guilty pleasure purchase you make without hesitation?
• What’s a weird hyper-fixation or rabbit hole you’ve gone down recently?
• What is your go-to karaoke song when you’re put on the spot?

Nostalgia & Growing Up

• What was your absolute favorite childhood toy or game?
• What’s the funniest or most embarrassing thing you did to try to look “cool” in middle school?
• What was your very first job, and what was the worst part about it?
• What meal immediately reminds you of home?
• What cartoon or show did you obsessively watch growing up?

Playful Relationship Starters

• What was your very first impression of me, and how has it changed?
• If we were a duo in an action movie, who would be the brain and who would be the muscle?
• What’s a hobby or activity you’ve never tried that you’d be willing to do together?
• What’s the most thoughtful gift you’ve ever received from anyone?
• If we had to design our ultimate date day with zero budget limits, what would we do?