100 questions to ask your crush that'll bring you closer together (2023)

If you’re looking for the perfect ice-breaker to start a conversation with your crush, then look no further.

I’ve personally selected the following 100 questions for you to ask your crush.

The best bit:

These questions will help you to get to know your crush at a deeper level so you can decide whether there’s potential for a long-lasting connection.

So if you have your eye on someone, grab the first opportunity to talk to them and ask them some of these 50 questions to find out if they are right for you, followed by 50 more bonus follow-up questions.

50 deep questions to ask your crush

1) What is the one thing you wish you hadn’t done in your lifetime?

2) Would you prefer to have smarts or happiness?

3) What is the reason for the last time you cried?

4) What scared the crap out of you but you did it anyway?

5) What’s one thing your siblings or parents don’t know about you?

6) What is one bad habit that you have? And don’t say you work too hard!

7) Who is your favorite superhero?

8) Name a cartoon character you think is hot.

9) If money were no option, where would you live?

10) What is your biggest pet peeve?

11) Who is the one person on earth that knows you better than anyone else?

12) What did you do for fun in high school?

13) When you were growing up, what did people think you were going to do with your life?

14) What’s your favorite book?

15) What’s your favorite television show?

16) What was your best age in life so far?

17) What’s the one thing you would tell your teenage self if you could go back in time?

18) What’s the one thing you want to do that when it’s done, you can die happy?

19) Do you prefer to apologize for something you did after the fact or ask permission first?

20) What would you prefer: money or love?

21) What’s on your bucket list?

22) What’s the song you listen to on repeat?

23) Would you rather spend a week on a beach or backpacking through Europe?

24) What is something you were really good at as a child?

25) What would you buy first if you won the lottery?

26) If you could trade lives with anyone, who would it be?

27) If you started a band, what would it be called?

28) What’s the one condiment you can’t live without?

29) What’s the one thing you did when you were younger that people still give you hell about?

30) Do you like small gatherings or big parties?

31) What’s been the worst year of your life so far?

32) What is the one thing that will end a relationship for you?

33) Who do you see yourself as if you were a fictional character?

34) Karma or revenge?

35) What was the best television show on when you were a child?

36) What is something weird that you like about people?

37) What’s the one topic in Trivial Pursuit you could clean up in?

38) Are you superstitious?

39) What was the worst day of your life?

40) What is your favorite terrible song?

41) Is there someone you want to run for president that hasn’t?

42) Who would you have dinner with if you could – dead or alive?

43) What was the best gift you ever got from your parents?

44) Do you wish we would go back to a time before the internet?

45) What would you give someone as a gift if money was no object?

46) What would you do if you could be the opposite sex for a day?

47) What’s the nicest thing anyone has ever said about you?

48) Would you rather live in a big subdivision style home or a tine lake house?

49) What is the one thing you hate about your family?

50) What’s your favorite flavor of ice cream?

Bonus deep questions and their follow-ups for a truly deep conversation

1) What do you do to calm yourself down when you are angry?
Possible follow-up questions: what kind of things make you angry? How long does it usually take you to calm down when something or someone has made you angry?

2) Have you ever tried to look cool and it backfired?
Possible follow-up questions: what made you think it was a good idea in the first place? How did you feel afterward? Did you ever try it again?

3) What is one rule you do not break in life?
Possible follow-up questions: how do you feel when other people break this rule? Is there a situation or scenario in which you would consider breaking this rule?

4) What is the biggest bullet you’ve ever dodged at work?
Possible follow-up questions: what about the times you didn’t dodge the bullet? What happened? Have you ever made the same mistake twice in this area?

5) What’s the one thing you’ve never been able to master or learn?
Possible follow-up questions: are there people in your life who can do this thing and how does it make you feel? Have you ever tried to seriously learn how to do this thing?

6) What is the coolest skill you have?
Possible follow-up questions: has this skill ever come in handy at work or in life or is it just for fun? Have you ever met someone else who can do this skill just as well as you?

7) How do you spend most of your time throughout the day?
Possible follow-up questions: if you could spend your day doing anything, what would it be? Have you ever spent an entire day doing anything?

8) What is the one thing you spend money on and you know you shouldn’t?
Possible follow-up questions: what do you do curb your spending? Do you feel guilty about your spending? Why don’t you just let yourself enjoy the thing you bought?

9) What’s an event that totally changed the course of your life?
Possible follow-up questions: do you ever wonder what might have been if you had done something else that day? What if someone had intervened?

10) Are you a serious person?
Possible follow-up questions: why don’t you let yourself have more fun? Have you ever had to deal with the fall out of not taking something serious in the past?

11) What is it about people that drive you crazy?
Possible follow-up questions: what do you do to help you overcome those judgments? Have you ever had to cut someone out of your life because they wouldn’t stop doing these things?

12) What is the most beautiful thing you’ve ever seen?
Possible follow-up questions: why do you think this experience stays with you? What would top this experience if you had the chance to do it? What’s your plan for making that happen?

13) What is the best compliment you’ve ever received?
Possible follow-up questions: what’s the best compliment you’ve ever given to someone else? Did you enjoy getting the compliment or giving one more? Do you like giving compliments to other people?

Whether you are transitioning from the friend stage to the couple stage, or you just meet a stranger over coffee after signing up for a dating app, these questions and potential follow-up questions can help you get to know someone faster than waiting around for these topics to present themselves.

The key to having a good conversation is to continue to listen first and ask questions second. If your conversation takes a turn and you aren’t sure where it’s headed, just listen. You always look like a great communicator when you listen.

Now that you’ve read the 100 questions to ask your crush to build deeper and more intimate relationships, we recommend doing something a little extra.

NOW READ:50 questions you must ask your partner before it’s too late