Questions to Ask Your Date

25 Questions to Ask Him or Her

One of the greatest things about beginning a new relationship is that you have the freedom to ask any sort of question that you desire – and they can be as eccentric as you wish. If you are genuine with your curiosity, then your partner will be grateful that you have questions about him or her, and the more fun they are, the more fun the conversation can be!

The whole point of dating is that you are getting to know a potential long-term partner. You want to find out about their relationships with friends and family, their spiritual or philosophical beliefs, their hobbies, and what they enjoy most in life. It is important to ask these questions, but to pose them in a way that is both fun to ask and fun to answer.

Here are some fun questions to throw into the mix.

1. What’s your favorite thing to do on Saturday morning?
2. What’s the best thing about Wednesday nights?
3. What’s your ideal second date?
4. What do you like best about thunderstorms?
5. What do you look for in a vacation?
6. What magazines do you read in the supermarket checkout line?
7. If you could choose an alternative career path, what would it be?
8. If you were going to teach any subject, what would you teach?
9. If you were going to learn any subject in school, what would it be?
10. Where is the best place for a month-long vacation?
11. Where is the best place for a one-week vacation?
12. If you were going to take six months off from work, what would you do?
13. What is the last thing you do before you go to bed?
14. What is the best thing about this town?
15. What are things about this town that are your secrets?
16. If you were going to live permanently anywhere else, what are your top 3 choices?
17. Who do you look up to when you need advice about life?
18. What things had made you change your mind about anything?
19. What philosophy do you subscribe to, if any at all?
20. What are fun weekend getaways in this state?
21. What is the most embarrassing thing that you have done in the last few weeks?
22. How does your mother describe you?
23. How does your best friend describe you?
24. How do you want me to describe you?
25. Would you like another date?