40 great speed dating questions to ask

The beauty of speed dating — in person or virtual — is that it gives you a way to meet new people face to face. The trouble is the clock: you have five to seven minutes per round, so the questions you ask need to do real work. Below are forty questions that get past “what do you do?” and tell you something useful about the person sitting across from you.

Pick a handful before the event, not all forty. Three or four good questions is plenty for a single round — what matters is how you listen and where you take the answer next.

If you haven’t been to a speed dating event before, What to expect at a speed dating event will walk you through how the night runs.

How to use these questions#

• Choose three to five favourites. Memorise them so you’re not reading off your phone.
• Don’t fire them off in a list. Use one, listen, follow up, then drift to the next.
• Match the energy. Open with something light; save the deeper ones for when the conversation has warmed up.
• Be ready to answer too. Almost every question here is one you should be willing to answer yourself.
• Take a tiny note after the round. A two-word reminder (“dog person, surfs”) is enough to bring the conversation back when you’re entering your picks later.

Warm-up openers#

Easy, low-stakes questions to start a round.

1. Do you think plants thrive or die in your care? Explain.
2. What’s been your happiest memory this past year?
3. What has been making you happy lately?
4. What is your favourite simple pleasure?
5. What is your favourite part of the day? Why?
6. What is your favourite time of the year and why?
7. Name one activity that always brings you joy?
8. Describe yourself in three words.

About them — childhood, identity, favourites#

A bit deeper. Use these once the round has settled.

9. As a child, what did you want to be?
10. As a child, what did you want to be when you grew up?
11. What is your favourite childhood memory?
12. What title would you give this chapter in your life?
13. What is your favourite material possession?
14. What is one thing most people don’t know about you?
15. What is your unique ability?
16. What activities make you forget about time and feel present in the moment?

Playful “guess about me”#

The flirtiest set. They turn the round into a tiny game and tell you how observant your date is.

17. What do you think my superpower is?
18. Do you think I’ve ever been fired from a job? If so, what for?
19. Do I seem like more of a creative or analytical type? Explain.
20. What subject do you think I thrived in at school? Did I fail any?
21. Do I seem like a cat or dog person?
22. What does my phone wallpaper tell you about me?
23. Do I seem like a morning person or a night owl? Why?

Values, fears and the future#

Use sparingly — one of these is usually enough per round. They reveal a lot.

24. What do you crave more of?
25. What would you do if you had no fear?
26. When was your finest moment?
27. What gives you the most pleasure in life?
28. How do you make important decisions?
29. What would you like to learn?
30. What would you most like to be remembered for?
31. If you had a choice between a nomadic or settled life, what would you choose and why?
32. Where do you feel most at home?
33. Share one of the fears you have been able to overcome.
34. What is something you will regret not doing in your life?

Quick-fire and closers#

Good for the last minute of a round when you can feel the bell coming.

35. Describe your perfect day!
36. Where is your favourite place in the world? Why?
37. Where would you live if you could live anywhere?
38. What is the first thing you notice about someone?
39. What qualities do you find most attractive in other people?
40. Do you like to follow or break the rules? Why?

A few questions to skip#

Some questions feel important but don’t belong in a five-minute round. They either kill the mood or pin people into defensive answers:

• Exes. Save this for date three, not minute four.
• Salary, job titles, postcodes. These sound like an interview.
• Politics or religion as a debate. Curiosity is fine; trying to win an argument in five minutes never goes well.
• Anything you wouldn’t want to be asked back.

One last tip#

The best speed-dating conversations aren’t the ones with the cleverest questions — they’re the ones where you actually listen. Pick a question, ask it, and then ask “really? why?” The follow-up is where the connection lives.

When you’ve finished the rounds, head back to Fanciful and log your picks against your scorecard. If you’d like a refresher on that step, see What to expect at a speed dating event.