Last Updated on October 1, 2020
Meeting your crush for the first time can be such a daunting experience. Since the meet-up isn’t technically a romantic date, you’d intuitively want to shy away from asking questions that border on their love and sex life.
However, there comes a point when you’ve gotten so comfortable with one another that you wouldn’t mind the conversation taking a flirtatious direction. If anything, your end-goal is to charm them into a romantic or sexual relationship with you.
We’ve rounded up some of the top questions to ask your crush to get to know them better. The questions have been sorted into various categories, ranging from basic questions that will help you break the ice to more profound questions about their personality and interests.
Questions About Their Family and Background
1. Where are your parents from?
2. Do you know how your parents met?
3. Are your parents still living in the same home you were born in?
4. Have your parents separated before (and what was the reason)?
5. How big is your family?
6. How close is your relationship with your parents?
7. Who is your parents’ favorite child?
8. Do you have an extended family? How close is your relationship with them?
9. What’s your nickname at home?
10. What’s the best thing you love about your parents?
11. What’s the most embarrassing thing you did when you were young?
12. What’s your favorite childhood memory?
13. How many of your childhood friends do you keep in touch with?
14. Which part of your past would you like to relive?
15. Which part of your past would you rather erase from your life permanently?
Questions About Their Hobbies, Interests, and Ambitions
1. Describe yourself in three words.
2. When is your birthday?
3. What’s your favorite quote from a novel, TV show, or movie?
4. What kinds of music/sports are you into?
5. What do you consider your best achievement so far?
6. What’s your greatest aspiration in life?
7. If you had a chance to be anyone for a whole day, who would you be and why?
8. What does a typical day look like for you?
9. What do you spend much of your money on?
10. Are you a mountain or beach person?
11. Are you a city or country person?
12. Are you an early bird or a night owl?
13. What’s the one compliment that you regularly receive?
14. What’s the one thing you’ve been mostly criticized about over the past one month?
15. What are your greatest phobias?
Questions About Their Past Relationship and Love Life
1. Does true love exist?
2. How would you define true love?
3. What is the most romantic thing you have ever done?
4. Have you been in a romantic relationship before?
5. Why did you break up with your ex?
6. What’s the one thing that you loathed the most about your ex?
7. What’s the one thing that you loved the most about your ex?
8. Can you give love a chance any day?
9. What’s the best thing you could do for love?
10. If love didn’t exist, what would be the next best emotion?
Profound Questions About Their Character and Personality
1. Can you sum up your life’s philosophy in one sentence?
2. If a genie grants you three wishes, what would they be?
3. Would you rather become rich or famous?
4. Would you rather be incredibly intelligent or incredibly happy?
5. What do you think the future of the world is going to be like?
6. In your opinion, what makes humanity successful?
7. What’s the best compliment that someone can receive?
8. How do you calm yourself down when you are angry?
9. What is the most ridiculous rule/fad you have to follow?
10. What’s your opinion on gender equality?
11. What’s your level of political/religious consciousness?
12. Are you a superstitious person and what are you mostly superstitious about?
13. Do you believe in fate or are we in control of our lives?
14. If you knew you would die in a month’s time, what would you do?
15. If you could be the opposite sex for one day, what would you do?
Flirtatious and Dirty Questions
1. What was your first impression of me?
2. What do you look for in a guy/girl?
3. What’s your idea of the perfect date?
4. What’s your biggest turn on when you’re on a date with someone?
5. What is your biggest turn off when you’re on a date with someone?
6. Do you believe in love at first sight?
7. In your opinion, what’s the primary cause of loneliness?
8. When was the last time you honestly felt appreciated or loved?
9. How can someone as cute as you be single?
10. How do you stay so attractive?
11. Are your parents as attractive as you?
12. What would you do if you accidentally saw me naked?
13. Do you prefer the lights off or on?
14. Do you like it when men take the lead or when women do?
15. Do you prefer casual dating or long-term relationships?
16. Would you rather hug for 5 seconds or kiss for 1 second?
17. How would you react if I told you that I like you?
18. Do you have any fetishes?
19. What’s your view on the role of sex in a relationship?
20. What would be your answer if I asked you out on a date?
A date with your crush is a golden opportunity to give a good account of yourself. It’s not just a chance to get to know them better, but also find out if they might be interested in pursuing a romantic or sexual relationship with you. Therefore, you should pull all the stops to make a lasting impression. And one way to do that is by arming yourself with the 70+ questions we’ve highlighted above.