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Top 100 Funny Dating Questions

Funny Dating Questions

This post contains some of the best funny dating questions, including “would you rather dating questions” to inspire you.

Funny Dating Questions

1. If you could have any superpower on a date, what would it be and why?

2. What’s the strangest pickup line someone has ever used on you?

3. If you were a food item, what dish would you be and why?

4. What’s the most embarrassing thing you’ve done on a date?

5. If you could switch lives with any fictional character for a day, who would it be and how would you use that day to your advantage?

6. What’s the funniest or weirdest nickname someone has ever called you?

7. If you could only eat one type of food for the rest of your life, what would it be and why?

8. What’s the most hilarious dating disaster story you’ve ever heard?

9. If you were a cartoon character, which one would you be and why?

10. What’s the most ridiculous thing you’ve ever done to impress someone you liked?

Related: Best 7 Emotional Intimacy Books

11. If you were a vegetable, what vegetable would you be and why?

12. What’s the most unusual or adventurous thing you’ve ever eaten?

13. If you could be any animal for a day, which one would it be and why?

14. What’s the most embarrassing song that you secretly love?

15. If your life was a sitcom, what would it be called and who would play you?

16. Which fictional character do you think would make the worst romantic partner?

17. What’s the most ridiculous fashion trend you’ve ever followed?

18. If you could invent one useless gadget, what would it do?

19. What’s the most bizarre rumor you’ve ever heard about yourself?

20. What’s the weirdest food combination that you secretly enjoy?

21. If you were stranded on a deserted island with one celebrity, who would you want it to be and why?

Related: Best 50 Ways To Stay In Love Forever With Your Partner

22. If you could be any Disney villain, who would you choose and why?

23. What’s the most unusual or interesting thing you collect?

24. What’s the most ridiculous thing you’ve ever bought while online shopping?

25. What’s the craziest dare you’ve ever accepted?

26. If you could rename yourself, what name would you choose and why?

27. If you could have a conversation with any historical figure, who would it be and why?

28. What’s the silliest fear you have?

29. If you could have any celebrity play you in a movie about your life, who would it be and why?

29. What’s your favorite cheesy joke?

30. If you could have any fictional creature as a best friend, which one would you choose and why?

Related: Top 10 Emotional Needs Of A Woman & A Man In A Relationship

31. If you were a flavor of ice cream, what would you be and why?

32. If you could instantly become an expert at any skill, what would it be and why?

33. What’s the strangest talent you have?

34. What’s the funniest movie or TV show you’ve ever watched on a date?

35. What’s the most hilarious text message you’ve ever sent or received during a date?

36. If you could create a new holiday, what would it be called and how would people celebrate it?

37. What’s the most unusual date activity you’ve ever participated in?

38. If you had a talk show, who would be your ideal first guest and why?

Related: Top 15 Journal Prompts For Relationship Anxiety

39. If you could travel back in time, which decade would you visit for a date and why?

40. What’s the most awkward encounter you’ve had with an ex-lover?

41. What would be the title of your autobiography if it was about your dating life?

42. What’s the strangest gift you’ve received?

43. What’s the silliest thing you’ve done to impress someone you’re interested in?

44. If your love life was a board game, which one would it be and why?

45. What’s the most ridiculous outfit you’ve ever worn on a date?

46. What’s the funniest opening line you’ve ever received on a dating app?

47. What’s the most hilarious date story you can share?

48. What’s the craziest coincidence you’ve experienced?

49. What would be your dream date if money and logistics were no issue?

50. What’s the most ridiculous excuse you’ve ever given or received to avoid going on a date?

Related: Top 9 Avoidant Attachment Triggers (+7 Tips On Overcoming Avoidant Attachment Style)

Would You Rather Dating Questions

1. Would you rather have more free time or have a higher salary? 

2. If you were to get married this year, would you rather have a big wedding or a small wedding?

3. Would you rather ask for help or figure it out on your own?

4. Would you rather be able to fly or read minds?

5. Would you rather be able to talk to plants or animals?

Related: Best 12 First Month Of Dating Tips – According To Science

6. Would you rather be able to travel but couldn’t stay anywhere longer than a week or never leave your hometown?

7. Would you rather be able to type and text really fast or be able to read really fast?

8. Would you rather be alone for the rest of your life or always be surrounded by annoying people?

9. Would you rather be beautiful and dumb or smart and unattractive?

10. Would you rather be forced to eat only spicy food or only bland food?

11. Would you rather be known for being funny, or for being kind? 

12. Would you rather be really funny or really smart?

13. Would you rather be rich or famous?

Related: Top 25 Relationship Journal Prompts (+FREE Worksheets PDF)

14. Would you rather be the funny one, or have your partner be the funny one?

15. Would you rather cook or wash the dishes? 

16. Would you rather die before or after your partner?

17. Would you rather die in 10 years with no regrets or live for 30 years with lots of regrets?

18. Would you rather experience physical pain or emotional pain?

19. Would you rather fly first class or stay at a luxury hotel?

20. Would you rather get up early or stay up late?

21. Would you rather give up social media or be an influencer?

Related: Dating With Intention: What Does It Mean & How To Do It?

22. Would you rather go for a long walk on the beach or a romantic drive through the country?

23. Would you rather go out once a week, or go on a date every night?

24. Would you rather go to brunch or have breakfast in bed? 

25. Would you rather go to jail for a crime you didn’t commit, or get away with a crime but be paranoid about being caught for your entire life?

26. Would you rather go to jail for a year or lose a year of your life?

27. Would you rather hang out with older people or with younger people? 

28. Would you rather have a partner with short hair or long hair?

29. Would you rather have a pet dog or a pet cat?

30. Would you rather have more time or more money?

31. Would you rather have poor short-term memory or poor long-term memory?

32. Would you rather have unlimited free flights or unlimited free food at restaurants?

Related: How to Avoid A Low Value Man & Find The Right One?

33. Would you rather have your mind stay sharp, or your body look young? 

34. Would you rather know how you die or when you die?

35. Would you rather live in a big city or a small town?

36. Would you rather live somewhere very cold, or live somewhere very hot? 

37. Would you rather live to be 100 years old or live to an average age but live rich? 

38. Would you rather live without the internet or live without AC and heating?

39. Would you rather lose all of the money you made this year or lose all of the memories you made this year?

40. Would you rather never be able to eat meat or never be able to eat dessert?

41. Would you rather never hear music again or never watch a movie again?

42. Would you rather never use social media again or never watch a TV show?

43. Would you rather only be able to go out during the day, or only be able to go out at night?

44. Would you rather pay for someone’s meal or have someone pay for yours?

45. Would you rather read a book or watch a movie?

Related: Am I Ready To Be In A Relationship Quiz (+Best Dating Tips For Women)

46. Would you rather spend a year living in an RV or on a sailboat?

47. Would you rather take a relaxing bath, or enjoy a steam shower? 

48. Would you rather talk on the phone or text?

49. Would you rather your partner’s parents dislike you, or your partner’s friends dislike you? 

50. Would you rather always be 10 minutes late or always be 20 minutes early?

200 Thought-Provoking Questions for Couples

Why Use Dating Questions?

1. Icebreaker

Dating questions serve as icebreakers to initiate conversations and help both individuals feel more comfortable with each other.

They provide a starting point and set a relaxed tone for the rest of the date.

2. Getting to know each other

Asking questions about hobbies, interests, values, and aspirations allows you to learn more about your date’s personality.

This helps establish a connection and creates a deeper understanding between both individuals.

3. Compatibility assessment

Dating questions can help determine whether you share common interests, goals, and values.

By exploring these aspects, you can assess compatibility early on and decide if you want to pursue a deeper relationship.

4. Emotional intimacy

Asking meaningful questions can facilitate emotional intimacy by encouraging open and honest communication.

This can lead to a stronger connection and a deeper level of trust between both individuals.

Related: Anxious Preoccupied Attachment Style (What Is It & How To Overcome It?)

5. Fun and enjoyment

Using dating questions that are light-hearted and funny can create a more enjoyable and relaxed atmosphere.

Laughter and humor can help build a positive and memorable experience, fostering a sense of enjoyment and bonding.

6. Avoiding assumptions

Asking questions allows you to avoid making assumptions about your date based on appearances or limited information.

It gives you the opportunity to gain a more accurate understanding of who they are as an individual.

Related: Earned Secure Attachment: What Is It And How To Become More Securely Attached?


The purpose of dating questions is to foster conversation, curiosity, and connection.

Respect your date’s boundaries and be mindful of their comfort levels.

Open-ended questions encourage more elaborate responses and lead to better conversation flow.

By Hadiah

Hadiah is a counselor who is passionate about supporting individuals on their journey towards mental well-being. Hadiah not only writes insightful articles on various mental health topics but also creates engaging and practical mental health worksheets.

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