206 First Date Questions to Break Awkward Silence

Are you planning a first date? If so, you know how nerve-wracking it can be to make conversation.

You’re not alone, many people struggle with finding topics to discuss on a first date.

Anyway, you don’t have to worry anymore – this article is here to help!

We’ve compiled 200+ first date questions that are sure to break any awkward silence and get the conversation rolling.

These questions will help you discover your date’s interests and goals, as well as their sense of humor. So, let’s get started.

10 Best Examples to Ask and Benefits

When it comes to planning a first date, the conversation is often one of the most important components. But what are some of the best first date questions in your conversation? The questions should include:

1. What do you like to do in your free time?

Asking this question can help you understand the other person’s hobbies and interests, which can give you insight into their personality and what they enjoy.

You may be able to find common ground, and it can also give you ideas for future dates. For example, if they enjoy hiking, you could plan a future date to go hiking together.

2. What’s your favorite place you’ve ever traveled to?

This question can reveal a lot about a person’s travel history, as well as their interests and tastes.

It can also give you insight into their personality, such as if they prefer adventure or relaxation, and also can give you an idea of where they would like to visit in the future.

3. What’s your favorite movie?

This question can help you understand the other person’s taste in movies, as well as their interests in general. It can also give you an idea of what type of movies they like to watch.

4. What’s your favorite book?

Similarly, this question can help you understand the other person’s taste in books. It gives you an idea of their reading preferences

5. What’s your favorite type of food?

This question can help you understand the other person’s taste in food, and also give an idea to select a restaurant for future dates.

6. What’s your dream job?

This question can reveal a lot about a person’s aspirations and goals, as well as their interests and ambitions. So, that you can compare their ambitions with your own.

7. What are you most passionate about?

This question can help you understand the other person’s interests and passions, which can give you insight into their personality and what they care about most.

8. What’s your biggest fear?

This question can help you understand the other person’s fears and insecurities. It can also give you an idea of how they handle difficult situations.

9. How would you describe your perfect day?

It can give you an idea of what type of activities they like to do on a perfect day. So, that you can make a hangout plan to impress them.

10. If you could live anywhere, where would it be?

This question can help you understand the other person’s preferences and aspirations, and can also give you ideas for future dates.

Ice Breaker First Date Questions

It’s often difficult to decide what to talk about; sometimes, it can feel like you’re navigating an awkward silence. Consider asking these first date ice breaker questions:

1. What is your favorite love ballad?

2. What’s the best dish you make?

3. Would you rather be very active or a lazy couch potato, given the choice?

4. What’s your favorite useless fact?

5. What is your favorite season?

6. What’s the worst advice you’ve ever been given?

7. If you had your own talk show, who would your first three guests be?

8. What’s your favorite joke to tell?

9. What was your first record, tape, or cd that you ever owned?

10. In what ways are you talented?

11. What is your funniest talent?

12. What is your favorite birthday cake flavor?

13. If you could hang out with any cartoon character, who would it be?

14. What is your favorite thing to do?

15. If you could have an unlimited supply of something for the rest of your life, what would it be?

16. What is the scariest thing you have ever experienced?

17. What’s the best thing you’ve got going on in your life at the moment?

18. What is your typical, everyday outfit like?

19. What’s your go-to drink order?

20. What movie do you never get tired of watching?

21. As a child, what did you want to be when you grew up?

22. What website or app doesn’t exist, but you really wish it did?

23. On a holiday, where do you go?

24. What’s the worst idea you’ve ever had?

25. What is your favorite thing to do after a tough day?

26. What is your favorite music type/genre?

27. What is your idea of an ideal life?

28. What takes a lot of time but is totally worth it?

Funny First Date Questions

Funny first date conversation starters can be a great way to break the ice and have some fun. It’s always a smart idea to have a few lighthearted topics in your back pocket, whether it’s your first date or you’re looking for a more creative approach.

1. What “old person” things do you do?

2. Is there anything you believed as a kid, for way too long?

3. What fad did you never really understand?

4. What things do you love doing, that people would never guess about you?

5. Do you have any guilty pleasures?

6. What’s your favourite guilty-pleasure show on TV?

7. If someone only saw your Spotify or Netflix accounts, what kind of person would they think you are?

8. What’s your go-to song for singing in the shower?

9. What’s always guaranteed to make you laugh?

10. Do you laugh at stale jokes politely, or find it hard to pretend?!

11. Have you ever had somebody call you the wrong name and not had the heart to correct them? If so, what did they call you?

12. What inappropriate moments have you found yourself getting the giggles, when you really shouldn’t have?

13. What’s the most embarrassing thing you’re afraid of?

14. What’s the longest lie-in you’ve ever had?

15. How bad is your road-rage on a scale of 1-10?

16. Have you ever been on the receiving end of a practical joke?

17. What’s the worst nickname someone has ever called you?

18. What did you normally get told off for when you were younger?

19. Do you have any claims to fame?

20. How about any secret hidden talents?

21. What’s the most embarrassing thing to happen to you on a first date?

22. What was your very first kiss like?! And how old was you when it happened?

23. If you were to give your younger self, one piece of dating advice, what would you say?

24. How nervous do you get on dates?

25. If you could dress me in anything, for the rest of this date, what would you put me in?

26. What would you rate me as a date so far?

Deep First Date Questions

Asking deep and meaningful questions will help you get to know each other better on a first date. These are several deep first date questions that will help break the ice and keep the conversation going in the right direction.

1. What three words would your mom use to describe you?

2. Would your boss choose you as his/her replacement?

3. If you could only choose one charity to donate to or volunteer for the rest of life, which would you pick?

4. What’s your most embarrassing childhood memory?

5. Which of the seven deadly sins do you commit the most often?

6. What’s your biggest irrational fear?

7. When I say “love,” what’s the first thing that comes to your mind?

8. Why do you think you’re still single?

9. If you could hire someone to help you, would it be with cleaning, cooking, or yard work?

10. Would you rather vacation in Mexico or Alaska, and why?

11. If you could tell your younger self one piece of advice, what would it be?

12. If you could live anywhere, where would it be?

13. Who is your hero?

14. What is your family member’s proudest accomplishment?

15. When you get into an argument, what’s your typical reaction look like?

16. Do you believe that everyone has that ‘one’ person they’re meant to be with?

17. Which is more important to you – emotional intimacy or physical intimacy?

18. Where do you see your next relationship ending up (marriage, casual-fling, and so on)?

19. What would your best friend say your worst quality is?

20. How important is religion to your life?

21. What quality do you like best in a partner?

Juicy First Date Questions

Finding the right words to ask on a first date can be difficult. Then use these engaging questions that can help keep your conversation interesting and give you insight into who they are as a person.

1. What quality attracted you towards me?

2. What are your biggest deal breakers?

3. Do you think men should always make the first move?

4. Who was your first love?

5. Have you ever kissed on a first date?

6. How was your first kiss?

7. Do you have any dirty secrets?

8. How do you feel about pajamas?

9. How do you think we would spend a day at home together?

10. How good do you think our first kiss will be?

11. What is the one thing you always wanted to change about yourself?

12. What is the biggest lie you have ever told?

13. When was the last time you cried?

14. Have you ever been arrested?

15. Any embarrassing habit I might not be able to guess?

16. What is your biggest fantasy?

17. What is the craziest dream you have had?

18. Any romantic gesture that always works on you?

19. What works on you, personality or looks?

20. Tell me a country you have always wanted to live in?

21. Are you tired of staying single for the longest time?

22. Want to go out on an ice cream date, the next time?

23. What do you do in your free time?

24. What was your favorite part of growing up?

25. Any regrets while growing up?

26. Do you like watching porn?

27. Have you ever been attracted to a woman? If yes – have you ever acted on it?

28. Does the thought of two men having s#x turn you on?

29. Have you ever made a s#x tape?

30. What do you fantasize about?

31. Have you ever been to a strip club?

32. Do you have a fetish?

33. Do you like to be dominated? Or do you prefer to be the dominant one?

34. What are your favorite places to be touched? Where are your least favorite places to be touched?

35. What is your favorite s#xual position?

Romantic First Date Questions

When it comes to first dates, many people struggle with finding the right questions to ask. This is especially true for those looking for romance from the beginning. The following are some romantic questions to ask on a first date:

1. What’s one thing I do that really makes you feel loved?

2. What does the perfect date night look like for you?

3. Do you think we have a lot of fun together?

4. Did you confess to your first crush? Who were they? How did it go?

5. Have you ever had your heart broken?

6. What date night atmosphere would you be most happy with?

7. Do you think physical touch is a big part of romance? Moreover, what gestures in particular do you find romantic?

8. Do you think any of our friends have a great couple life? Should we follow their example?

9. What’s the first thing you thought about me when we met?

10. What’s one thing you really like about me, physically speaking?

11. What do you think is my favorite thing about you?

12. If we had all the money in the world, what’s the first thing you’d want us to do together?

13. What’s one life lesson you’d pass on to the next generation?

14. Have your thoughts about relationships remained constant throughout your life?

15. Do you believe in staying friends after breaking up?

16. What’s one meal you’d like to have for a romantic night?

17. Is there a specific music genre that “gets you going”?

18. Do you think I look good in my outfits?

19. If you could only choose 1 cuisine for the rest of your life, what would it be?

20. Do you think our relationship is lacking in something specific?

21. What made you think of me as more than a friend?

22. Do you think there’s a secret to staying happy in a relationship?

23. Is there a romantic movie you want us to watch together?

24. Can you describe me using just 3 words?

25. Do you think we had a great first kiss or was it mediocre?

26. How would you describe being in love? Is there something in particular you feel?

27. Do you have any fears or phobias that you find strange?

28. Do you think you’re a jealous person? Am I a jealous person? What do you think about jealousy overall?

29. What does romance mean to you?

30. Did you go through a “phase” growing up?

First Date Questions about Personality

To ensure that you get to know your date better, here are some important questions to ask on a first date about personality in order to learn more about the person you are dating.

1. Do you enjoy evening strolls?

2. What was the best part of this date?

3. Do you like to make things yourself?

4. Do you like to follow a fixed routine?

5. Do you clean your house before you have guests, or is it always clean?

6. For how long have you been in this city?

7. How often do you take yourself out to treat yourself?

8. How often do you like spending time outdoors?

9. Are you a beach person or mountains?

10. What is the worst job you have ever done?

11. What are your go-to things to do every weekend?

12. How often do you cook?

13. How often do you and your best friend meet?

14. Do you like to share your food?

15. What food can you eat every day?

16. What is the one tourist place you always wanted to visit?

17. How often do you listen to podcasts?

18. Do you like to read about a place before visiting, or like walking in straight?

19. Do you like to explore technology?

First Date Questions about Work

Having a great conversation on a first date can be daunting, but asking the right questions can make all the difference. Here are some great first date questions to create a good impression on first dating:

1. What does a perfect day at work look like?

2. Have you always wanted to do what you are doing?

3. At what priority would you keep your career and work in your life?

4. How many times in a day do you curse yourself for choosing this line of work?

5. What are rest and off days in your life like?

6. What do you do to earn a living?

7. Are you excited to go to work every day?

8. Does work feel stressful sometimes?

9. Do you ever wish you could change career paths?

10. Why did you choose to do what you do?

11. Do you want to stay in your field or explore something new?

12. Are you passionate about what you do?

13. Is there a profession that you’ve always had a curiosity about but never pursued?

14. What was your dream job as a child?

15. If you could go back in time, knowing what you know now, is this the exact job you would’ve chosen for yourself?

16. Were you always in this profession, or did you change careers?

17. Do you have working weekends?

18. Is there a colleague at work you are absolutely crushing upon?

19. If success was guaranteed, what would you have done?

20. If given an option to be anything, for one day, what would you do?

21. Who is someone you absolutely love at work?

22. Is your boss a pain?

23. How often do you feel like shooting your boss in the head?

24. How much weight did you gain after joining the office?

25. Do you prefer to work from home, or love your office cubicle?

First Date Questions about Hobbies and Interests

If you’re looking to make a good impression on your first date, it’s important to ask questions about their hobbies and interests. Here is a few first date questions to ask:

1. What is something you really want to do, only if you have time by your side?

2. What is a hobby you know no one can beat you at?

3. How often do you make time for your hobbies and passions?

4. What do you think your biggest contribution to this world is?

5. Any special skills you can teach me?

6. What is your hidden talent?

7. Do you have a tattoo?

8. What is your spirit animal?

9. Are you big on social media?

10. Why do you think you were put on this planet?

11. How often do you like to hit the gym?

12. Are you a fan of pop culture?

13. What did you do last weekend?

14. Where was the last trip you took?

15. Do you have any trips planned for the near future?

16. What do you want your next adventure to be?

17. Are you currently working on something you are really passionate about?

18. What is a recent hobby you picked?

19. What is something you have been doing for the longest time?

20. How important are your hobbies to you?

Final Thoughts

It is normal to feel nervous or uncomfortable on a first date. Asking the right questions can help break the ice, take the pressure off both of you, and make it easier to get to know each other.

Our list of 200+ interesting first date questions is an excellent tool to help break awkward silences.

These questions are designed to help you get acquainted, learn more about each other, and figure out if there is potential for a future relationship.  

It’s ultimately about being present and engaged in the conversation, so go forth and make those connections! And don’t forget to appreciate us in the comment box.

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