New Study Reveals 232 Funny First Date Questions (+ Questions Not To Ask On A First Date)

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Are you looking for funny first date conversation starters for a first date? You’re in the right place! Studies have shown that humor and laughter can be powerful tools to create connection and build relationships.

By asking funny questions on your first date, you can make yourself and your date laugh together, or at least talk about topics you wouldn’t usually talk about, which will trigger some interest and even laughs together. It’s a good way to connect and avoid the usual same boring first date talks. 

In addition to couple’s truth or dare questions, those funny things help you start a conversation and laugh together while getting to know each other as well.

Based on our new study and our experiences dating in Canada, Santa Barbara and Ireland, we share the most fun questions to ask on a first date, including funny flirty questions and funny relationship questions.

New study finds these 10 questions to be best for a first date

Though we have created 311 funny questions for a first date, we also gathered data first hand from our valuable audience on social media (18,000 followers). This allows us to get data and feedback right from real couples and people! From our survey, here is the top 10 funniest questions to ask on a first date:

1. Were Rachel and Ross on a break?
2. If Rachel and Ross were on a break, was it wrong of Ross to sleep with someone else?
3. What day of your life would you want to relive again and again?
4. What Hogwarts house would you choose?
5. If I had to have one flaw, what would you pick?
6. Do you pull toilet paper over or under?
7. Which social media platform would you delete forever?
8. Would you rather have hair for fingers or fingers for hair?
9. Do you share your food with your partner?
10. What actor or actress would you pick to play me in a movie?

Though these questions seem just funny at first, they break the ice to enter into revealing topics. For example, your perception of whether Rachel and Ross were on a break has to do with your communication style. Some people thing they were clearly on a break through the words and actions they communicated while others think that they were still together.

By asking these questions, you will learn more about your date’s perception of different situations, their views and values along with their communication style. These are very important pieces of information when deciding whether you’d want to go on a second date with them.

General funny questions for your first date 

Questions to ask on first dates can be difficult to find. You want to be funny but also learn something about the person. In this section, we share some funny date questions that are perfect for a first date general conversation.

11. If you could be any mythical creature, what would you be and why?
12. What’s the most useless talent you have?
13. If you could only eat one color of food for the rest of your life, what would it be?
14. Would you rather live in a world without coffee or without chocolate?
15. What’s the craziest conspiracy theory you’ve heard and do you believe it?
16. If you were a superhero, what would your catchphrase be?
17. What’s the weirdest dream you’ve ever had?
18. If you could only watch one TV show for the rest of your life, what would it be?
19. What’s the most embarrassing thing in your closet right now?
20. If you were a character on The Office, which one would you be and why?
21. What’s the most ridiculous thing you’ve ever done to impress someone?
22. If you were stuck on a deserted island and could only have one book, what would it be?
23. What’s your go-to karaoke song?
24. Is you first impression of me positive or neutral?
25. What’s the first thing you’d do if you were a crab?
26. If you were a type of pizza, what toppings would you have?
27. Who would you want to be related to?
28. What’s the most bizarre fashion trend you’ve ever tried?
29. If you could be any character from a childhood game or movie, who would you choose?
30. If you could only communicate in emojis for a day, how would you express yourself?
31. If you had a warning label, what would it say?
32. Who was your first celebrity crush?
33. What’s the most ridiculous thing you’ve ever done for a dare?
34. If you were a video game character, what would your special move be?

Funny first date questions to ask a man

Here are some good first date questions to ask him that are also funny:

35. If you were a vegetable, what kind would you be and why?
36. If you could only eat one food for the rest of your life, what would it be?
37. If you could have any superpower, but it had to be completely useless, what would it be?
38. If you could switch lives with any person for a day, who would it be and why?
39. If you could have any animal as a pet, regardless of how practical it is, what would it be?
40. If you were stranded on a desert island and could only have one book, what would it be?
41. If you could time travel to any era in history, where would you go and why?
42. If you were a character on a TV show, which one would you be and why?
43. If you could switch lives with any celebrity for a day, who would it be and why?
44. Do you have any phobias or fears that people would find unusual?

Funny first date questions to ask a woman

Men and women are built different so questions to ask a girl on a first date are different from those you’d ask a man.  Here are some funny questions to ask a woman on a first date:

45. If you could be any Disney villain, who would you be and why?
46. If you were a dessert, what kind of dessert would you be and why?
47. Would you rather fight one horse-sized duck or 100 duck-sized horses?
48. If you could be any fictional character, who would you choose and why?
49. Do you have any weird habits or quirks?
50. What’s the most embarrassing song on your playlist?
51. If you could have any animal as a pet, regardless of how practical it is, what would it be?
52. What’s the worst pickup line you’ve ever heard?
53. If you could have any superpower, but it had to be completely useless, what would it be?
54. What’s the most secret hidden talents you have?
55. If you could live anywhere in the world, where would you choose and why?

Funny online dating questions to ask him

These are some of the best questions to ask on a first date with a man when the dating is happening on a dating app.

56. If you could live inside any TV show for a day, which one would it be and why?
57. What’s the most ridiculous thing you’ve ever bought online?
58. Would you rather be stuck on a deserted island with a celebrity or a fictional character?
59. What’s the weirdest thing you’ve ever googled?
60. What’s the most embarrassing thing you’ve ever said on a first date?
61. What’s the most ridiculous thing you’ve ever done to impress someone?
62. If you had to shave your head, would you wear a wig or be bald?
63. If you had to change your name, what would you change it to and why?
64. If you could only watch one movie for the rest of your life, what would it be?
65. If you were a character in a video game, what would be your weapon of choice?
66. If you could be any character from a book, who would you choose and why?
67. If you had to choose between being a professional clown or a professional mime, which one would you choose?
68. If you could have any superpower, but it had to be completely useless, what would it be?

Funny online questions to ask her

Online dating or meeting has become more of the norm in the past few years. Here are some funny questions to ask on a first date that’s happening online. 

69. If you could only wear one color for the rest of your life, what color would it be?
70. If you were a Disney princess, which one would you be and why?
71. What’s the most useless talent you have?, one of the funny first questions to ask your first date
72. If you had to eat one type of food for every meal, what would it be?
73. If you were a superhero, what would your catchphrase be?
74. How long did you believe in Santa Claus?
75. If you could be any character from a book, who would you choose and why?
76. What’s your go-to karaoke song?
77. On a scale of 1-10, how good are you at parallel parking?
78. Can you fold a fitted sheet?

Funny creative first date questions

In this section, we share fun first date questions that are perfect for creative people.  These are fun questions to ask on a date where you’re going to be doing something artistic like or simply if your date is artistic. 

79. If you were an art medium, which one would you be and why?
80. If you could create a new color, what would it be and what would you name it?
81. If you could design your dream house, what would it look like?
82. If you were a musical instrument, which one would you be and why?
83. If you could collaborate with any artist, living or dead, who would it be and what type of art would you create?
84. If you were to write a book, what would it be about?
85. If you could have any fictional character as your personal assistant, who would it be and why?
86. If you could time travel to any concert in history, which one would you choose?
87. If you were to start your own business, what would it be and why?
88. If you could have any famous artist paint your portrait, who would it be and why?
89. If you were to create your own comic book character, what would their superpower be?
90. If you could design your dream fashion line, what type of clothes would you create?
91. If you could star in any movie, which one would it be and what character would you play?
92. If you could have any famous chef cook you a meal, who would it be and what dish would you want?
93. If you could be any character in a Broadway show, who would you choose and why?
94. If you could create your own museum exhibit, what would it be about?
95. If you could have any famous author write your biography, who would it be and why?
96. If you could only listen to one genre of music for the rest of your life, what would it be?
97. If you were to create your own podcast, what would it be about?
98. If you could be any artist from history, who would you choose to be and why?

Funny interesting first date questions

These interesting date questions can sometimes give funny answers which will help you laugh together and get to know each other better. These are great funny first date conversation starters:

99. What’s the most important thing on your bucket list?
100. If you could have dinner with any historical figure, who would it be and why?
101. What’s the most spontaneous thing you’ve ever done?
102. If you could have any job in the world, but only for a day, what would it be and why?
103. What’s the most interesting thing you’ve learned recently?
104. If you had to choose between being able to fly or being invisible, which one would you choose and why?
105. If you could have any talent, what would it be and why?
106. If you could have any famous musician perform at your birthday party, who would you choose and why?
107. If you could have any job in the world, regardless of qualifications or education, what would it be and why?
108. If you could have any famous person as your personal butler, who would it be and why?
109. If you were a cartoon character, what catchphrase would you have?
110. If you could switch lives with any fictional character for a day, who would it be and why?

Funny random date questions

Random dating questions can help you know your date much better than serious questions. See some of them here:

111. If aliens landed on Earth tomorrow and asked you to go with them, would you go? Why or why not?
112. What’s the most random food combination you’ve ever had?
113. If you could be any mythological creature for a day, which one would you choose and why?
114. If you were given a million dollars, but had to spend it all in one day, what would you buy?
115. If you were stranded on a desert island and could only bring one item, what would it be and why?

Funny spicy questions to ask on a first date

When wondering what questions to ask on a first date, you’ll want to appreciate your date’s culture, experience and background. That said, if the mood is right, spicy questions to ask on a first date or flirty first date questions can be a good way to go about it. In this section, we share some fun dating questions that are more sexy!

116. What’s the sexiest thing you’ve ever done?
117. If you could choose one celebrity to be your “Hall Pass,” who would it be?
118. If you could describe your ideal kiss in three words, what would they be?
119. Have you ever had a naughty dream about someone you know? Who was it?
120. If you could have any superpower in the bedroom, what would it be?
121. Have you ever skinny-dipped before? If not, would you like to?
122. What’s your biggest turn-on and why?
123. Have you ever sent a naughty text to the wrong person? What happened?
124. If we were alone right now, what would you want to do?
125. What’s the sexiest piece of clothing you own?
126. If you had to choose one body part to compliment me on, what would it be?
127. What’s your favorite spot to be kissed?
128. What’s the wildest place you’ve ever hooked up?
129. Would you rather go skinny-dipping or have a steamy make-out session in the rain?
130. If we were playing strip poker right now, who do you think would win?
131. What’s the naughtiest thing you’ve ever done on a date?

Hilarious questions to ask on first date that are also romantic

A first date doesn’t mean there can’t be any romance. Here are some romantic questions to ask on a first date:

132. What’s the cheesiest pick-up line you’ve ever used on someone?
133. What’s the most romantic gesture you’ve ever received or given to someone?
134. What’s your favorite romantic comedy movie and why?
135. What’s the most spontaneous romantic thing you’ve ever done for someone?
136. If you could have a date anywhere in the world, where would it be and why?
137. What’s the most embarrassing romantic moment you’ve ever had?
138. What’s the most romantic song you’ve ever heard?
139. What’s your favorite love poem or quote?
140. What’s the most memorable romantic date you’ve ever been on?
141. If you had to describe your ideal partner in three words, what would they be?
142. If you could have any fictional character as your soulmate, who would it be and why?
143. What’s the most unique romantic gift you’ve ever received or given?
144. If you could have any love scene from a movie or TV show recreated for you, which one would it be?
145. What’s the most romantic thing anyone has ever said to you?
146. If you could go back in time and relive one romantic moment from your past, which one would it be?
147. If you could write a love letter to someone, who would it be and what would you say?

Funny personal questions to ask on a first date

Personal questions to ask on a first date are very important as they’ll help you get to know your date better.  Here are some of our favorite personal questions to ask a first date:

148. What’s your biggest fear and how do you deal with it?
149. What’s the craziest thing you’ve ever done and would you do it again?
150. What’s something you’ve always wanted to learn but haven’t had the chance to yet?
151. What’s your biggest pet peeve and how do you deal with it?
152. If you could be any character from a book, who would you choose and why?
153. What’s your guilty pleasure, whether it’s a TV show, movie or hobby?
154. What’s something you’re passionate about and why?
155. What’s the most embarrassing thing that’s ever happened to you?
156. What’s something you’re really good at that people might not know about?
157. If you could travel anywhere in the world, where would you go and why?
158. If you could have any three wishes granted, what would they be?

Funny but important questions to ask on a first date

Questions you ask on a first date can really determine if the relationship will progress into something more and better. Here are some funny but important questions to ask on a first date.

159. What’s your career goal? To be the CEO of a Fortune 500 company or to become a professional Netflix binge-watcher?
160. What’s the one thing you absolutely won’t compromise on? Besides your love for tacos, of course.
161. Would you rather live in a tiny house with a huge yard or a huge house with a tiny yard? Asking for a friend who’s an imaginary real estate agent.
162. What’s your favorite conspiracy theory?
163. Do you think it’s possible to be both successful and happy? Or is it more like a choose-your-own-adventure book where you can only pick one?
164. What’s your ideal way to spend a weekend? Is it catching up on sleep or staying up all night watching cat videos on YouTube?
165. Do you have any secret talents? Like being able to recite pi to a hundred digits or knowing how to breakdance?

Funny questions to ask before a first date

Though we are sharing great questions to ask on a first date to be funny and connect together, there are also questions to ask before first date meetings. Here are some of them:

166. So, how do you feel about social media background checks?
167. Have you ever Googled someone before a first date? Asking for a friend.
168. Would you say that you’re more of a catfish or a trout?
169. Do you have any allergies or aversions to pepper spray?
170. Have you ever had to use a self-defense move on a first date?
171. Are you good at tracking down IP addresses? I need a favor…
172. If we end up running into your ex on our date, can we pretend to be siblings?
173. Do you have any experience with restraining orders? Just in case.

Funny deep questions for a first date

Some of the best questions for a first date are funny and deep questions. Good questions for a first date should help you get to know your date better while keeping things light and helping you laugh together. That’s what those questions do for you:

174. What’s the most embarrassing thing you’ve ever done in the name of love?
175. If you could have any superpower that helps you cope with heartbreak, what would it be and why?
176. What’s your most embarrassing date story?
177. Are you more of a right-brain or left-brain person?
178. Do you know what your love language is?
179. What are three words your mom would use to describe you?
180. Do you think everyone has that ‘one’ person or soul mate they’re meant to be with?
181. What’s the most valuable lesson you’ve learned from a past relationship?
182. If you could write a letter to your future self about love, what would you say?
183. If you only had 48 hours left to live, what would you want to do in those last few hours?
184. Tell me two truths and a lie, and I’ll try to guess which is the lie.
185. What hobbies would you like to pursue if you had the time and money?
186. Do you speak any other languages?
187. Do you consider yourself a morning person or a night owl?, you can ask this before planning a date during the morning.
188. Tell me the craziest thing on your bucket list.
189. What’s the worst outdoor date you’ve been on? 
190. If you could only have one love song on your playlist, which one would it be and why?
191. If you found yourself suddenly transformed into a man/woman, what would you do?
192. What is your worst first date experience?
193. If you had to pick one rom-com to watch on repeat for a month, which one would it be and why?
194. What’s your biggest fear when it comes to falling in love and how do you deal with it?

Funny first date questions to make you think

Asking questions on a first date is easy but asking good questions for first date meetings can be a bit more tricky. If you’re wondering what questions to ask on the first date to make you and your date think, here are some that we recommend: 

195. If you could be any historical figure for a day, who would it be and what would you do?
196. If you could ask any scientist one question, who would it be and what would you ask?
197. Which would you prefer: to be able to time travel to any period in history, or to be able to see into the future?
198. Which would you prefer: to have a photographic memory or to have the ability to forget anything you choose?
199. Which would you prefer: to live in a world without art or a world without science?
200. Which would you prefer: to have a career as a famous author or a famous musician?
201. Which would you prefer: to be able to speak and understand every language in the world or to be able to speak to animals?
202. Which would you prefer: to have the ability to teleport or to have the ability to fly?
203. Which would you prefer: to be the smartest person in the world but also the most disliked, or to be of average intelligence but well-liked by everyone you meet?
204. Which would you prefer: to be stranded on a deserted island with only a copy of your favorite book or with a lifetime supply of your favorite food?
205. Which would you prefer: to be able to live without sleep, or to be able to sleep for as long as you want and always wake up feeling rested?
206. Which would you prefer: to have a photographic memory but always be physically clumsy, or to have perfect physical coordination but a terrible memory?
207. If you could choose one language to become fluent in instantly, which would it be and why?
208. If you could have dinner with any philosopher, dead or alive, who would it be and why?
209. If you could live in any era in history, which would it be and why?
210. Which bread do you think would fly the furthest – a naan tossed like a Frisby or a baguette thrown like a javelin?
211. If you could have any question answered, what would it be?
212. If you could be any fictional character for a day, who would it be and why?
213. Which would you prefer: a horrible short-term memory or a terrible long-term memory?
214. If you were arrested and no explanation was given, what would your friends and family suppose you had done?
215. If you could choose to be immortal, would you do it? Why or why not?

Funny icebreaker questions for a first date

First dates can be stressful! And asking questions on first date can feel a bit forced. In this section, we share with you some funny questions for first date to ask to break the ice and get things going.

216. What was the most random thing you’ve ever found on the internet?
217. Do you have any nicknames or funny stories behind your name?
218. If you could live in any era of history, which would you choose and why?
219. What’s your go-to dance move at a party?
220. If you were stranded on a deserted island and could only bring three items, what would they be?
221. Have you ever pulled a prank on someone? What did you do?
222. Have you ever had a celebrity crush? Who was it?

First date conversation starters

Whether you’re looking for questions to ask a guy on a first date of funny first date questions to ask her, the following questions are great conversation starters. They’ll help you get out of awkward silences or just to kick off conversation fi you’re both nervous. 

223. If you could go anywhere in the world right now, where would you go and why?
224. What’s your favorite hobby or activity to do in your free time?
225. Do you have any pets or have you had any in the past?
226. What’s your favorite book, movie or TV show and why?
227. Have you ever traveled solo? If not, would you ever consider it?
228. What’s the most interesting thing about your job or profession?
229. What’s the most adventurous or spontaneous thing you’ve ever done?
230. Do you enjoy trying new foods or restaurants? What’s your favorite type of cuisine?
231. If you could have dinner with anyone in history, who would it be and why?
232. What’s your dream vacation or trip and why?

Funny questions you shouldn’t ask on a first date

Whether you’re looking for funny questions to ask a man on a first date or funny questions to ask a girl on first date, there are some questions that no-one should ever ask on a first date. Here are some of them:

1. Can I see a photo of your driver’s license to confirm your age?
2. Do you believe in aliens? Have you ever been abducted?
3. Do you mind if I take a quick nap? I’m pretty tired.
4. Can I borrow some money? I left my wallet at home.
5. Do you know any good pick-up lines? Asking for a friend.
6. Can I check my phone real quick? I’m waiting for an important text.
7. Do you like my outfit? It’s my lucky first date outfit.
8. What’s your weight?
9. Do you always wear that much makeup?
10. Would you be willing to change your style?

Funny first date questions tips

In the above sections, we shared many funny questions to ask on a first date with a man or a woman. Although these are fun questions to ask a date, there are times where fun date questions are inappropriate. Here are some tips to ensure you use them to have a successful date. 

Avoid invasive funny questions on a first date

We agree that funny questions are a great way to break the ice on a first date, but be careful not to cross the line and ask overly personal or invasive questions. Remember that you are just getting to know each other, so keep the questions light and fun and make sure your date is feeling comfortable at all times.

Stop asking funny questions if your date isn’t receptive

While some people love to laugh and joke around, others may not be as receptive to funny questions. If you sense that your date is not enjoying the funny questions, it’s time to change the subject and move on to other topics and approaches.

Learn two or three questions by heart before

To avoid awkward silences or feeling unprepared, it’s a good idea to have a few funny questions memorized before your first date. This will help you feel more confident and relaxed, and ensure that the conversation flows smoothly. Just make sure to choose questions that are appropriate for the situation and your date’s personality.

Take into account where you are

Before asking funny questions, we recommend checking where you are and what’s considered appropriate there. Even across the USA, cultures differ and what’s acceptable when dating in Dallas, might not be acceptable when dating in Utah or when going on a date in Boston. 

Our experience

We’ve been together for years and went on many different romantic dates both at home and when we traveled to couple’s destinations. We’ve also had several first dates, some that went well and some that didn’t go so well. 

We’ve found that funny questions can really help relax the atmosphere on a first date. Whether you’re going on a date hiking or a date at the beach, first dates can be difficult as you have to juggle between getting to know each other, connecting but also being respectful and avoiding awkward silences.

Indirectly, these funny questions actually teach you a lot about the person sitting across from you in addition to breaking the ice. That definitely helped us decide, in the past, whether we wanted to go on a second date with the person or not! Seems to have worked out well enough for us since we’re now happily married!

FAQs

Now that we’ve shared all funny dating questions for a first date, we thought we would conclude this post with a FAQ.

Any questions on these funny first date questions? Drop them in the comments or on insta and we will get back to you asap.