40 Questions to Ask on a Second Date

The first date was small talk. The second is where you find out if there’s something there. Start easy, follow up, and only go deeper when it feels natural.

Easy openers

1. What was the best part of your week since we last saw each other?
2. What’s something you’re looking forward to this month?
3. What do you do when you have a completely free Saturday?
4. What’s the last thing that made you laugh out loud?
5. What’s your go-to comfort food?
6. Are you a planner or a “let’s see what happens” person?
7. What’s a small thing that instantly improves your day?
8. What’s the best thing you’ve watched or read lately?
9. Coffee, tea or neither, and how do you take it?
10. What’s a place nearby you think is underrated?

Getting to know them

1. What does a normal weekday look like for you?
2. What got you into the work you do now?
3. Who in your life do you talk to most?
4. What’s something you’ve changed your mind about in the last few years?
5. What are you proud of that people don’t usually ask about?
6. What’s a skill you’d love to learn?
7. Where did you grow up, and what was it like?
8. What’s a tradition from your family you still keep?
9. What does a really good friend do, in your view?
10. What’s something on your list to do before next year?

Fun and playful

1. What’s your most useless talent?
2. If you could only eat one cuisine for a year, which one?
3. What’s a hill you will absolutely die on?
4. Which fictional place would you move to?
5. What would your walk-up song be?
6. What’s the strangest job you’ve ever had?
7. If we had a free plane ticket for tomorrow, where are we going?
8. What were you obsessed with at age 12?
9. What’s your karaoke song, even if you never sing it?
10. Would you rather have a great garden or a great kitchen?

A little deeper (when it feels right)

1. What does a good relationship look like to you?
2. What makes you feel appreciated?
3. How do you like to spend time when you’re stressed?
4. What are you hoping the next couple of years look like?
5. What’s something people often get wrong about you?
6. What’s a value you got from your parents, or chose differently?
7. When do you feel most like yourself?
8. What’s one thing you need in order to trust someone?
9. What did you learn from your last relationship?
10. What made you say yes to a second date?