Deep questions that aren't too deep to ask on a second date

These conversation starters will help you avoid the second date funk

Second dates can be hard. You’re transitioning from the light, sparkling banter of a first date to deeper stuff. You know you need to be vulnerable to find out if this is a good match for you, but this person is also still basically a stranger. We’re here to help you navigate these tricky waters with deep questions that aren’t too deep. You’ll get to know the person but neither of you will leave the date feeling laid bare. Unless that’s how you want it to go (wink wink).

1. What’s the best present you’ve ever received? What’s the best present you’ve ever given someone else?

2. Do you sleep in a cold or warm room?

3. Who knows you best? Tell me about them.

4. When you look around your apartment/house and think “I need to clean” is it because it’s messy, dirty, or both?

5. What do you think is the best thing about being an adult?

6. If you had an extra room you could use for anything, what would you use it for?

7. What would you rather someone do for you after a bad day at work: listen while you talk about your troubles or order your favorite food for you?

8. What’s the first food you want to get when you come home after a long trip?

9. If I were to open your closet door right now, what would fall on me?

10. When was the last time you cried?

11. Who was your favorite teacher?

12. If all jobs paid the same, what would you do?

And last but not least, the most important question of all: When can I see you again?


P.S. Not quite sure how to get to the second date? Here are some ideas for how to follow up after a great first date.

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