Anna Buckley/HelloGiggles
Alaina Leary
November 13, 2018 8:50 am

How well do you know the girl you’re dating? Chances are, if you’ve been together for a while (or you two talk a lot), you think the answer is obvious. But relationships are all about connection, and there’s nothing more fun than finding creative ways to have new conversations. If the relationship is new, you could start with some basics. But if you get the sense that she’s into being open and you feel comfortable getting to know each other on a deeper level, you can start talking about everything from childhood favorites to political views.

To help you get the words flowing, we’ve come up with a list of 40 important questions to ask a girl you’re dating. You can pull these out during your next date or wait for a special moment. They might work well if you’re both having a blah day and don’t know what to talk about besides how bad your day was. Or you can roll them out one at a time when it feels right, whether you’re in line at the store or celebrating an anniversary.

1. What’s your favorite holiday tradition, and why do you love it?

2. Did you vote in the last election?

3. Do you remember your first childhood pet?

4. If you had to wear one outfit for the rest of your life, what would you wear (accessories and all)?

5. How did you tell your very first crush that you liked them?

6. What was your least favorite subject in elementary school?

7. If you wear lipstick, what’s your favorite shade?

8. If you could pick one book to read over again every year, what would it be? (If she already does this, ask her why she chose that book.)

 9. Do you ever spend an entire day in bed?

10. What’s your favorite time of day?

11. If you could design an ideal super villain, what would they be like? What would their powers be?

12. If you could learn to play a new instrument, which would you choose?

13. What’s your favorite show that’s currently airing?

14. What’s your favorite show of all time?

15. Do you remember the first place you lived?

16. Who are the three fictional characters you think are most like you?

17. What is one thing people always assume about you that isn’t true?

18. What’s your idea of the perfect date?

19. If you could change anything about this country politically, what would it be?

20. Who taught you the most important skill you have?

21. If you could have all your meals prepared for you forever, would you do it? What would you ask the chef to make?

22. Do you have any daily habits you want to break?

23. What’s your morning wake-up routine?

24. Have you ever had a really good conversation with a stranger? What did you talk about?

25. Have you ever traveled alone, or would you?

26. Are there any words that just get on your nerves?

27. Who are you most envious of, and why?

28. What’s your favorite ’90s movie?

29. Are you proud of what you’re doing with your time right now?

30. If you could go back to school to study something new, what would it be?

31. What food will you absolutely never eat?

32. Are you a city person or do you prefer more space and fewer people?

33. When was the last time you cried?

34. Is there anyone in your life you want to have a better relationship with?

35. What’s one of your favorite memories from every season?

36. What would be your strategy for surviving a zombie apocalypse?

37. Who is the worst guest you’ve ever had?

38. What is your favorite obscure fact?

39. Who is the most grateful person you know?

40. What do you wish people would stop asking you?

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