While conversation comes easy to most, sometimes it can be a struggle. This can be apparent on a first date. While you may have been exchanging messages all week, it is a different situation when you are sat across from each other. All the charm and wit you possess in your texts might have abandoned you in the real world. Nobody likes an uncomfortable silence, especially on a date, so you need to have some questions to ask on a first date ready to go.

To help you out this article has a list of 101 of the best questions you can ask. These are all guaranteed conversation starters that will help you in your time of need. If you can’ maintain a convo after using some of these, then you might need to seek more help.

Ice Breaker Questions

These are general questions to get the ball rolling. They aren’t too in-depth and won’t reveal anything deep about your date, but they are good to see if you have any common interests from the get-go.

1. Why did you agree to this date?
2. What is something you’ve always wanted to do but were afraid to?
3. Who is your best friend and why?
4. What is your middle name?
5. Where is your favorite place in the world?
6. What is your favorite/worst movie?
7. Where is the best place you have lived?
8. What is your favorite/worst book?
9. Where did you grow up?
10. How big is your family?
11. Do you play any sports?
12. What is your favorite sports team?
13. What is your favorite genre of music to listen to?
14. Who is your favorite musician/actor/writer?
15. What did you want to be as a kid?

Personal Questions

Dive a little deeper and find out more about your date and their life. These questions will probe their personality so you can see what they are really like.

1. Where do you see yourself in 10 years?
2. What goals do you have for the future?
3. Would you consider living overseas?
4. Are you an early riser or a night owl?
5. How often do you like to exercise?
6. Are you an introvert or an extrovert?
7. How would you describe your personality?
8. What are your best and worst qualities?
9. Are you a good communicator?
10. What kinds of things make you the most upset?
11. What makes you happy?
12. Are you a calm or firey person?
13. What do you like most about yourself?
14. What is something you are really proud of?
15. Do you want to get married?
16. Do you want kids?
17. What is your biggest achievement in life so far?
18. What are your passions in life?
19. How do you want to be remembered when you are gone?

Family Questions

You want to date someone who puts their family first, and these questions will help you discover that. They are general in nature but give a good overview of whether your date is a family-oriented.