105 Best Questions to Ask Your Crush on a First Date (And Possibly Land a Second Date!) (2024)

First dates can be exciting, but tough. It’s easy to get comfortable texting someone, or to flirt and share quick stories about your day while strolling down the hallway, but the real challenge comes when you and your crush finally schedule your first date. Not only do you have to coordinate the perfect outfit, you have to know what to talk about beyond the initial, “Hi, how are you?” How do you steer the conversation away from small talk? What if the conversation lulls? Luckily, there are endless first date questions that will help you build a connection, learn a lot about your crush, and possibly land a second date.

From breaking the ice to wrapping the night up, asking questions during a first date indicates that you’re interested and engaged in the conversation. You may not want to ask a ton of questions all at once — that might make the date seem like an interview, and that can feel intimidating. But sprinkle questions in here and there to fill gaps in the conversation and avoid awkward silences. Without much effort, you’ll create a totally easy and natural rapport. So without further ado, here is a comprehensive list of perfect first date questions to ask your crush during every stage of the date.

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Questions for the First Couple of Minutes

If you don’t know each other, this is the part of the date where you’re both nervous and maybe feeling a little awkward. While it might be tough to come up with some questions, sometimes just sticking to the basics is key.

1. How are you? / How was your day?
2. What classes are you taking right now?
3. What do you want to study/are studying?
4. Where do you go to college/plan on going to college?
5. Where do you work?
6. Do you have any plans for [insert upcoming school break or summer vacation here]?
7. Do you have social media?
8. Do you hang out in this neighborhood often?
9. How do you know [insert mutual friend here]?
10. Tell me more about yourself.

After Breaking the Ice

Once you’re more comfortable (and you know you want to spend more time with this person), you’re ready to get to know them better. Some fun and easy questions can help liven up the conversation.

1. What do you do for fun?
2. Do you want to go to college in-state or out-of-state?
3. What’s your favorite TV show/movie?
4. What TV show did you last binge-watch?
5. What was the best concert you’ve ever been to?
6. Who’s your favorite musician/band?
7. Do you have a favorite book or favorite author?
8. What clubs or activities are you in?
9. Do you have any siblings?
10. Do you have any pets?
11. What’s your favorite place to go to around town?
12. Do you have a hidden talent?
13. What’s your favorite food?
14. What’s your least favorite food?
15. What’s your go-to place for take out?
16. Who’s your celebrity crush?
17. What’s your favorite ice cream flavor?
18. What’s your favorite sport? / Who’s your favorite professional sports team?
19. What’s your all-time favorite candy?
20. What’s your go-to karaoke song?
21. Do you prefer the indoors or the outdoors?
22. You can only bring three items to a deserted island. What do you bring?
23. Who would play you in a movie about your life?
24. What would be your superpower?
25. If you won the lottery, what would you buy?
26. If you were elected President, what would you do first?
27. If you could live in any other time period, what would it be?
28. What’s the last movie you saw?
29. What’s your favorite local coffee place?
30. What’s your favorite holiday?
31. What’s your favorite season? Least favorite?
32. What type of music do you listen to?
33. Who are your favorite creators to follow on TikTok?
34. Do you believe in ghosts or any paranormal activity?
35. Would you rather time travel to the future or the past? Why?
36. Do you play any instruments?

When You Want More Info

After finally getting to know more about their personality, it’s time to start bringing up the deeper questions. This is the time to ask more ~make it or break it~ questions that can help you figure out if you may want a relationship with this person, or at least another date, like what’s on their bucket list or what their dream job is.

1. What are your dreams?
2. What is your favorite memory?
3. If you can talk to anyone dead or alive, who would it be and why?
4. What is your family like?
5. Are you close with your family?
6. What does your perfect weekend look like?
7. Are you a morning person or a night person?
8. What’s on your bucket list?
9. Do you have any nicknames?
10. What is your biggest guilty pleasure?
11. What is your favorite place in the whole world?
12. Who is your best friend and how did you get so close?
13. What’s something most people haven’t done, but you have?
14. If you could travel anywhere in the world right now, where would you go?
15. What is your ultimate dream job?
16. What’s something about yourself that you think would surprise me?
17. Are there any hobbies or subjects that you’d like to learn?
18. Do you consider yourself an introvert or an extrovert?
19. What issues facing our country are most important to you?
20. Have you ever attended a protest?
21. If you could live in any city in the world, where would it be?
22. What’s the best piece of relationship advice you’ve ever received?
23. What have you done recently for the first time?
24. What is your favorite way to relax?
25. What’s the most embarrassing thing that ever happened to you?
26. Do you consider yourself a religious or spiritual person?

When the Night Is Almost Over

It’s time to decide whether or not you want to extend your first date, possibly go on a second date, or just call it a night and move on. Ask some more intimate questions now that you’re both more comfortable, and see if things might work out between you two.

1. What are your goals?
2. What’s most important to you?
3. What do you see your future like?
4. Where do you see yourself in five years?
5. What are you most passionate about?
6. What are some of your biggest pet peeves?
7. What do you fear?
8. Do you have any regrets?
9. What’s your proudest accomplishment in life (so far)?
10. Who inspires you?
11. Do you believe in soulmates?
12. How would you describe yourself in three words?
13. How would you describe me in three words?
14. What was your first impression of me?
15. Do you know your love language?
16. What scares you the most about getting older? What excites you the most?
17. What made you want to go on this date?
18. When was your last relationship?
19. Why did your last relationship end?
20. What do you consider red flags in a relationship?
21. Do you believe in second chances?
22. What are you looking for in a relationship / partner?
23. What excites you about the future?
24. What worries you about the future?
25. What about me stands out to you the most?
26. What’s something you think people misunderstand about you?
27. If you could change one thing from your past, what would it be?

When It’s Time to Go

Depending on how you’re feeling, you might want to just end your possible relationship with your date right then and there. However, if you’re hoping to secure a second date, then these questions can help your crush get the hint.

1. Did you have a good time tonight?
2. Are you busy later this week?
3. Do you want to hang out again sometime?
4. Can I text you later?
5. Do you want to split the check or want me to pick up the next one?
6. Would you want to check out [insert movie/show/restaurant here] sometime?