200 best funny first date questions to ask him or her

Going on a first date can be extremely nerve-racking. You’re bursting with anxiety because there’s so much pressure on you to perform. Instead of relaxing and getting to know someone new, you’re constantly trying to think three steps ahead and make sure you don’t run out of things to say.

That’s where this list of funny first date questions can really save the day. All you have to do it memorize your favorites, and ask them whenever the conversation falters or you think the dreaded awkward silence is coming.

To make things easier, I’ve divided the list into three sections. Funny ice-breakers will help you get the conversation started, funny questions once the date is underway and you feel more comfortable, and flirty questions for when things are going really well.

I hope you find the list useful.

Funny first date questions to break the ice

These questions are perfect conversation starters to break the ice and get to know your date. Most people love to talk about themselves so you’ll have a lot of success with these funny first date questions.

1. What would be the topic of your TED talk? 
2. What was your favorite candy when you were a kid? 
3. What do you never get bored of talking about? 
4. Have you ever met a celebrity?
5. What’s your favorite thing to cook? 
6. If you could go anywhere on vacation, where would you go?
7.  Are you are dog person or a cat person? 
8. What’s your favorite late night snack? 
9. What would you do if you won 1 million dollars today?
10. Do you prefer the city or the country? 
11. What’s the worst job you’ve ever had? 
12. What is the best movie you’ve seen recently?
13. What is the most embarrassing thing you’ve done on a date?
14. Is your car as clean as your house right now? 
15. What is the funniest thing you’ve seen in the last year? 
16. Do you believe in the supernatural? 
17. What did you want to be when you were a kid? 
18. What’s the best advice you’ve ever received? 
19. What’s the worst date you’ve ever been on? 
20. If you had to move to a new country, where would you go? 
21. What do you spend the most time doing? 
22. When was the last time you dressed up for Halloween? 
23. What are your guilty pleasure movies or tv shows? 
24. What are you proud of but never have an excuse to talk about?
25. What is the most ordinary thing about you?
26. What’s the best date you’ve ever been on? 
27. What is something that I wouldn’t believe about you?
28. What does your dream home look like? 
29. What sports did you do in junior high or high school?
30. What’s your favorite way to exercise? 
31. What was the best band or act you’ve ever seen live?
32. How would you describe yourself as a kid? 
33. What do people do that annoys you the most? 
34. What is the stupidest thing you’ve seen in the last year? 
35. In one sentence, how would you sum up your life?
36. How did you meet your best friend?
37. What’s your favorite book of all time? 
38. Who is your biggest celebrity crush? 
39. What’s the best vacation you’ve ever been on? 
40. Would you rather vacation in the mountains or near the ocean? 
41. What would you most like to improve about yourself? 
42. What are the best and worst parts of your personality?
43. Are you a morning person or a night person?
44. What is your favorite city and why?
45. What do you get the most compliments about? 
46. What would be your dream job?
47. Have you ever experienced anything that felt too good to be true? 
48. What skill do you have that not many people would know about? 
49. What’s your biggest accomplishment so far in life? 
50. What is something that most people get wrong about you?
51. What aspect of your personality would you change if you could?
52. Would you rather be alone or in a crowd? 
53. What’s your weirdest habit?
54. Would you rather have a quiet night in or go out and party?
55. What do you find funny that isn’t actually funny?
56. What personality trait do you admire most about yourself?
57. Is it more important to be liked or respected?
58. What does your perfect weekend look like?

Funny first date questions to ask once you feel more comfortable

Once the date is well underway and you feel more comfortable it’s time to ask the real questions. These funny first date questions will show your sense of humor and your date will think you’re hilarious.

1. What’s the most embarrassing item of clothing you own? 
2. What’s something you’ve done that you wish everyone should experience?
3. What’s something illegal that you’d love to do?
4. What do you think you know a lot about but probably don’t?
5. What song do you always sing along with whenever you hear it?
6. What would your rapper name be? 
7. What superpower would you most like to have?
8. What ingredients are on the perfect pizza? 
9. What animal makes the funniest sound? 
10. What’s your biggest pet peeve about the opposite sex?  
11. What thing do you love, but was a complete waste of money? 
12. What would you do with your time if you never had to work? 
13. What would be the title of the movie about your life?
14. How would you describe social media in one sentence? 
15. What’s the best compliment you’ve ever received? 
16. If you could only eat one food for the rest off your life, what would you choose? 
17. What flavor combination is kind of weird but you really like it?
18. If you could be celebrity for a day, who would you be?
19. If you were granted three wishes, what would you wish for? 
20. If you had a disease named after you, what would be the symptoms?
21. What’s the worst gift you’ve ever received, and who was it from?
22. What’s your go-to karaoke song? 
23. What is the strangest thing that ever happened to you?
24. If you could trade places with anyone in the world, who would you choose? 
25. What do you find hard that most people find easy? 
26. What’s the worst joke you know? 
27. What could I do to make the best impression on your parents? 
28. Are you a night owl or a morning person? 
29. What’s the longest you’ve ever gone without sleep? 
30. What conspiracy theory would you like to invent? 
31. What’s the first thing that you do when you get home?
32. What do you think would be the coolest animal if they could talk? 
33. Would you rather be able to only whisper or only shout everything?
34. What ingredients are on the perfect burger?
35. Who would you spy on if you knew you wouldn’t get caught? 
36. What’s the most bizarre thing you’ve ever seen in someone’s house?
37. What advice would you give your 5 year old self? 
38. Would you rather have the ability to fly or teleport?
39. If you could re-live one day of your life again, which day would it be? 
40. What’s the best prank you’ve ever pulled on someone?
41. Would would your last words be? 
42. What’s the worst food you’ve ever eaten?
43. if you had to live without on appliance forever, what would you pick? 
44. What’s the worst smell in the world? 
45. What’s the most valuable thing you’ve ever broken?
46. If you were caught doing a crime, what would you friends assume you did? 
47. What would you do to get fired if there were no consequences? 
48. Have you ever been kicked out of a restaurant or bar? 
49. What item of clothing would you never leave your house wearing? 
50. What’s the best Wi-Fi name you’ve seen?
51. What small thing makes you angrier than it should?
52. What did you think was stupid until you tried it?
53. What would be the worst way imaginable to die? 
54. What’s the craziest thing you’ve ever done?
55. What’s something that everyone looks stupid doing? 
56. If you could stay at any age forever, what age would you pick? 
57. What’s the most embarrassing thing you’ve ever done?
58. What game do you dominate when you play it?
59. If you could give yourself a nickname, what would it be? 
60. What are you embarrassed to admit scares you? 
61. What’s the weirdest dream you’ve ever had? 
62. If you could choose to live in another time period, what would you choose? 
63. What’s the spookiest thing you’ve ever seen? 
64. What thing do you still enjoy that you loved ass a kid?
65. What thing always makes you laugh? 
66. What was fun to do once, but you’ll never try to do again?
67. What is the most interesting piece of trivia you know?
68. Would you rather have noisy neighbors or nosy neighbors?
69. What song comes on as your soundtrack when you get into a fight?
70. What’s the creepiest thing you’d say to stranger?
71. What do you judge people for that you probably shouldn’t?
72. What the worst name you could ever give a child? 
73. What would you miss the most if it suddenly became illegal? 
74. Should you ever put pineapple on pizza? 
75. What thing bores you the most in life? 
76. What move scared you the most when you were a kid? 
77. What’s the dumbest rule you’ve been forced to follow?
78. If you could be the best in the world at one skill, what would it be? 
79. Do you believe any conspiracy theories are true? 
80. Would you rather stay in a luxury hotel or go camping for the weekend? 
81. Who is the weirdest member of your family? 
82. Would you reset your life and do it again if you had the chance? 
83. What two things should never go together?
84. What’s the weirdest thing you’ve ever searched on Google?
85. If you had a warning label, what would it say?
86. Would you rather have $50 cash today or $100 cash one year from today?
87. If you could have one superpower, what would you choose?
88. What’s the most useless thing you’ve ever spent money on?
89. If you could only keep three things you own, what would they be?

Funny & flirty first date questions to ask once things are going well

If you’re getting along well with your date, it’s time to turn up the heat a little and ask some more flirty and funny questions. None of them are too forward, but your date will have no doubt that you’re interested.

1. Do you think you’re good at flirting? 
2. What celebrity would you want a free pass to sleep with?
3. What’s your favorite pickup line? 
4. Have you ever bought lingerie to impress a guy?
5. What accessories would be included with your action figure? 
6. What do you think guys / girls like about you the most?
7. Are you naughty or nice? 
8. Have you ever been seriously jealous? 
9. What’s the most romantic movie you’ve ever seen?
10. What is your favorite thing to wear to bed?
11. What color underwear are you wearing right now? 
12. What’s something adventurous you’ve never done but would love to try? 
13. How often do you look at your own butt in the mirror?
14. What happened on the last bad date you went on?
15. What’s the funniest thing you’ve ever done while drunk? 
16. What’s the most embarrassing thing in your bedroom? 
17. What’s the weirdest sex dream you’ve ever had?
18. What’s the worst pickup line anyone has ever tried on you? 
19. Have you ever gone out without wearing underwear? 
20. Where are you most ticklish? 
21. Have you ever sexted someone? 
22. What is your idea of the perfect date?
23. Would you rather good sex or good conversation? 
24. Would you rather be called sexy or cute?
25. Do you think we’d make a good couple?
26. What was your first impression of me? 
27. What’s the sexiest gift you’ve ever received?
28. Has anyone ever walked in on you naked?
29. Have you ever broken someone’s heart?
30. What do you think is your best physical feature? 
31. Do you prefer a passionate kiss or a long warm hug?
32. Do you believe in soulmates?
33. What’s the sexiest girls name? 
34. Would you let your boyfriend pick out your clothes? 
35. What was your first kiss like, and who was it with?
36. What is the most naughty thing you’ve done?
37. Has anyone ever broken your heart? 
38. Do you think you’re good at keeping secrets? 
39. How would you describe me in one sentence? 
40. What’s the craziest thing you’ve ever done for love? 
41. What’s the most important non-physical quality you look for in a guy / girl?
42. What’s your favorite place to be massaged?
43. How many times have you been in love?
44. What turns you on the most? 
45. What’s something about yourself you’ve never told anyone else? 
46. What’s the worst first date you’ve ever been on? 
47. What’s the dumbest thing you’ve ever done for love?
48. Would you go on a date with someone that your parents introduced you to?
49. What is one thing you would change about your body if you could?
50. Is flirting cheating?
51. What feature makes a guy and girl most attractive? 
52. What’s the biggest lie that someone you’ve dated has told you?
53. What would your porn star name be?

How to use these questions

The most important thing is to use these questions sparingly. Pick your favorites and keep them on standby if you’re struggling for something to say. When you’re on a date, you want the conversation to flow as naturally as possible. You don’t want to sound like a robot going through a list of questions or your date will feel like they’re being interrogated.

So, if you’re having a hard time getting the conversation started, fire away with one of these questions and see where the conversation takes you.

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