The Top 101 Best Questions To Ask on a First Date

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.

1. What do your parents do?
2. Do you have siblings, and if so, how many?
3. Are you close to your parents?
4. Are you close to your siblings?
5. Do you have a big family?
6. How often do you see your parents?
7. What was your childhood like?
8. What is one of your favorite childhood memories?
9. Are you still friends with any of your childhood mates?
10. Where did you go to high school?
11. Are you still friends with any of your high school mates?

Work Questions

Have a chat about their work and what they do. While it doesn’t define you, work does say a lot about who you are and what you are into.

1. Where do you work?
2. Do you enjoy your current job?
3. What do you love/hate about your current job?
4. Do you see yourself staying at your current job for a long time?
5. What is your favorite job you have ever had?
6. Do you get along with your work colleagues?
7. What was your first job?
8. What do you admire about your boss?
9. Would you like to work overseas?
10. How did you get into your current career path?
11. What is the worst job you have ever had?
12. Did you have to study, and if so, what did you study?
13. What is the longest time you’ve stayed in the one job?
14. What is your dream job?

Values Questions

Discuss her values and see if they line up with yours. You don’t want to date someone who doesn’t have the same morals as you.

1. Are you religious, if so, what do you believe?
2. What are your political leanings?
3. What social issues are you passionate about?
4. Who are the most important people in your life?
5. What are your personal values?
6. What do you want out of life?
7. Has Covid-19 changed your outlook on life?
8. What attributes do you look for in friends?
9. How important is your family?

Hobby/Passion Questions

Find out her interests and what she enjoys doing with her spare time. You may find you have some things in common you didn’t know about.

1. How do you spend your spare time?
2. What are some of your favorite hobbies?
3. Do you have any hobbies from childhood that you still pursue?
4. What is the latest hobby you have started to enjoy?
5. Do you share any hobbies with your friends?
6. What are your passions in life?
7. What goals would you like to accomplish this year?
8. Is there something you are passionate about that you would like to learn more about?

Relationship Questions

Now we are getting to the nitty gritty. Find out what she wants from a relationship and get some background on her previous relationships. This will let you know what to expect moving forward.

1. What are you looking for in a partner?
2. What does your ideal relationship look like?
3. How do you find dating apps?
4. Have you had any successful relationships from using them?
5. What is the best thing about dating you?
6. What is the worst thing about dating you?
7. How long have you been single?
8. What was your longest relationship?
9. What is was your shortest relationship?
10. How many times have you been in love?
11. Have you ever told someone you love them?
12. Are you a romantic?
13. What was your biggest heartbreak?
14. Do you enjoy dating?
15. Who gives you relationship advice?

Sex Questions

If the conversation goes down this route, here are some not too creepy questions you can ask. Don’t get too involved in this line of questioning and only bring it up if your interactions head this way.

1. Do you believe in sex before marriage?
2. What are your thoughts on casual sex?
3. What does the word sex mean to you?
4. Who was your first kiss?
5. When did you lose your virginity?
6. Do you enjoy talking about sex?
7. What is your biggest turn-on?
8. What is your biggest turn-off?
9. Do you believe in the three-date rule?
10. Who is your celebrity crush?