First dates can be awkward and yes, boring. Other times frightening. You’re not even sure what awaits you. But honey, you’re not alone out there – ’cause we got funny questions you can ask on a first date to remove those jitters.
Sure you can start with a small talk but after a while it can get boring and strained. To make matters worst, uncomfortable silence ensued.
Oh, no.
But need not fear now if you have a date tonight. These hilarious dating questions will save your night from all awkwardness and nervousness.
So prepare yourself for a date full of laughters and giggles.
Funny Questions To Ask On A First Date To Remove Awkwardness
1. If you could have any superpower, but it had to be completely useless, what would it be?
This sort of question gives you insight into your date’s sense of humour, creativity, and personality quirks. How they respond to the question can give you a glimpse into their imagination and what they find amusing. Remember, humour plays a role in having a long-term relationship.
2. What’s the most embarrassing thing you’ve ever done in public?
Since you’re both on a date, it’s only right to know more about your date’s personality. And asking this is one of the perfect ways to make your date talk more about embarrassing moment of his life.
His answer gives you a glimpse of the vulnerable side of him that he’s willing to share with you which will deepen your connection.
3. If you were a vegetable, what vegetable would you be and why?
It’s not a typical question but it allows your date to think creatively and use their imagination. It might sound very peculiar for your date, but it doesn’t hurt to answer this silly question and it might lead to unique and unexpected responses, sparking a fun and engaging conversation.
4. What’s the weirdest thing you’ve ever eaten?
This sparks an intriguing conversation that gives you a hint of your date’s personality about having new cultural experiences and preferences and adventurousness. If you’re thinking of getting into an interracial relationship, this question gives a glimpse of your date’s personality to welcome your own culture in his life once you both wanted to take a step forward from dating to being in a relationship.
5. If animals could talk, which one do you think would be the rudest?
Your date’s answer to this question can ignite a playful and imaginative conversation on your first date. It also allows you both to share funny observations and opinions about animal behaviour. But also on a serious side, discussing this gives you a hint of your date’s behaviour towards animals. Men who love animals are empathic and compassionate, according to Good Men Project.
6. If you could only eat one food for the rest of your life, what would it be?
It’s a simple yet effective way to start a conversation about food, preferences, and even cultural influences, setting a relaxed and enjoyable tone for the date.
7. What’s your most irrational fear?
This gives you an opportunity for empathetic conversation and can lead to shared laughter or commiseration over irrational fears, creating a more relaxed and intimate atmosphere during the date.
8. If you could swap lives with anyone for a day, who would it be and why?
It sparks conversation about desires, dreams, and the qualities they admire in others, offering insight into their aspirations and perspectives on life.
9. What’s the funniest movie you’ve ever seen?
It creates an opportunity to bond over shared comedic experiences and may lead to recommendations for future movie nights or outings, enhancing the connection between you and your date.
10. If you could time travel, which period would you visit first?
It offers insight into their curiosity about different eras and may lead to engaging discussions about the past, present, and future, fostering connection and shared interests between you and your date.
11. If you could only listen to one song for the rest of your life, what would it be?
It prompts reflection on the significance of music in their lives and may lead to discussions about memories, emotions, and personal experiences associated with the chosen song, deepening the conversation and fostering connection between you and your date.
12. What’s the most unusual talent you have?
It provides an opportunity for lighthearted discussion and may lead to laughter or amazement, creating a memorable and enjoyable exchange between you and your date.
13. If you could invent a holiday, what would it be and how would we celebrate it?
It invites discussion about shared values, traditions, and the spirit of celebration, fostering a fun and engaging exchange that may lead to shared laughter and the creation of new memories between you and your date.
14. What’s the craziest dream you’ve ever had?
This can lead to fascinating insights into their subconscious, sparking imaginative and entertaining conversation.
15. If you could be any fictional character, who would you choose?
It offers a glimpse into your date’s aspirational traits and the qualities they admire, sparking imaginative and insightful conversation.
16. If you were stranded on a desert island, what three things would you want to have with you?
It leads to discussions about personal values, resourcefulness, and the importance of connection, fostering deeper understanding and shared insights between you and your date.
17. What’s the most embarrassing thing that’s ever happened to you on a date?
It creates an opportunity for lighthearted storytelling and laughter, allowing both individuals to bond over humorous anecdotes and common dating mishaps.
18. If you could trade lives with one person for an entire day who would it be and why?
It sparks conversation about different lifestyles and perspectives, fostering deeper connection and understanding between you and your date.
19. What’s the silliest nickname you’ve ever had?
It invites playful reminiscing and lighthearted storytelling, fostering a fun and relaxed atmosphere during the conversation.
20. If you could only watch one TV show for the rest of your life, what would it be?
It opens up discussions about favorite characters, memorable moments, and the impact of storytelling on personal enjoyment, fostering a shared appreciation for television and potential recommendations for future viewing.
21. If you could only wear one color for the rest of your life, what would it be?
What they would choose to wear for the rest of their life reveals insights into their personal style, preferences, and perhaps even their emotional associations with colors.
22. What’s the weirdest thing you’ve ever seen in someone else’s house?
It leads to humorous storytelling and shared experiences, creating a playful and engaging atmosphere during the conversation.
23. If you could have dinner with any three people, dead or alive, who would they be?
It prompts reflection on individuals who have made significant impacts on their lives, fostering meaningful conversation and potentially revealing shared interests or new perspectives between you and your date.
24. What’s the weirdest dream you’ve ever had?
Asking this creates an opportunity for laughter, introspection, and sharing of personal experiences, fostering a deeper connection and understanding between you and your date.
25. If you could be any mythical creature, which would you choose?
It prompts imaginative exploration of mythical realms and fosters a playful exchange that reveals insights into their aspirations and sense of wonder, deepening the connection between you and your date.
26. If you could have any job in the world, what would it be?
This opens a window into their passions, interests, and aspirations, sparking engaging conversation about career goals and personal fulfillment.
27. What’s the most embarrassing thing you’ve ever done at work or school?
Asking about the most embarrassing thing your date has done at work or school invites humorous anecdotes and shared experiences, fostering a sense of camaraderie and understanding.
28. If you could have any animal as a pet, what would it be?
Asking someone about the animal they would choose as a pet sparks conversations about their affinity for nature, personality traits they admire, and their ideal companionship. This also gives you a hint if keeping a pet with him is a possibility.
29. What’s the weirdest fact you know?
It leads to sharing of unusual and fascinating tidbits, fostering a fun and informative exchange that can lead to laughter or thought-provoking discussions during the date.
30. If you could only eat one cuisine for the rest of your life, what would it be?
It prompts discussion about flavors, cooking styles, and personal connections to food, fostering a deeper understanding of their tastes and potentially leading to shared culinary experiences and recommendations.
31. What’s the most embarrassing thing your parents have ever caught you doing?
It creates an opportunity for laughter and empathy, strengthening the bond between you and your date through shared vulnerability and lighthearted storytelling.
32. If you could live in any fictional universe, which would you choose?
It prompts exploration of different worlds, characters, and storylines, fostering a playful exchange that deepens understanding and potentially uncovers shared interests between you and your date.
33. What’s the most embarrassing thing you’ve ever worn?
Asking about the most embarrassing thing someone has ever worn encourages light-hearted storytelling and sparks laughter over fashion mishaps and quirky outfit choices.
34. If you could only communicate in emojis for a day, how would you get your point across?
It invites playful exploration of the versatility and limitations of emojis, fostering lighthearted conversation and shared laughter between you and your date.
35. What’s the most unusual pet you’ve ever had?
It prompts conversation about unconventional pets, their care, and the bonds formed, fostering a lighthearted exchange and potential shared appreciation for the unusual.
36. If you could be any flavor of ice cream, what would you be?
It sparks imaginative conversation about tastes, emotions, and personal identity, fostering a fun and enjoyable exchange between you and your date.
37. What’s the weirdest place you’ve ever been to?
It leads to discussions about unique experiences, unusual locations, and memorable travels, fostering a lighthearted exchange and potentially uncovering shared interests or intriguing stories between you and your date.
38. If you could only eat one condiment for the rest of your life, what would it be?
It invites playful exploration of food choices and preferences, fostering a lighthearted exchange and potentially revealing shared tastes or culinary adventures between you and your date.
39. What’s the funniest joke you’ve ever heard?
It invites shared humor and amusing anecdotes, fostering a connection through laughter and potentially leading to memorable moments between you and your date.
40. If you could only watch one movie for the rest of your life, what would it be?
It prompts discussions about favorite characters, memorable scenes, and the enduring impact of film, fostering a shared appreciation for cinema and potentially leading to recommendations for future viewing experiences.
41. What’s the strangest thing you’ve ever seen on the internet?
It leads to conversations about internet culture, viral phenomena, and memorable online moments, fostering a lighthearted exchange and potential shared interests or amusing discoveries between you and your date.
42. If you could only wear one type of shoe for the rest of your life, what would it be?
Asking this helps you explore your date’s footwear preferences and potentially reveals insights into their fashion sense and lifestyle, fostering a lighthearted exchange and mutual understanding between you and your date.
43. What’s the most embarrassing thing you’ve ever said to someone you liked?
It creates a shared moment of empathy and understanding, fostering a lighthearted atmosphere and potentially leading to laughter and relatable experiences between you and your date.
44. If you could be any cartoon character, who would you be?
It encourages imaginative discussion about beloved characters, their adventures, and the qualities that resonate with them, fostering a lighthearted exchange and potential shared appreciation for animated storytelling between you and your date.
45. What’s the weirdest dream you’ve ever had that you can remember?
It leads to discussions about symbolism, interpretation, and the mysterious nature of dreams, fostering a lighthearted exchange and potential shared experiences between you and your date.
46. If you could only listen to one band or artist for the rest of your life, who would it be?
It prompts discussions about favorite songs, memorable performances, and the enduring impact of musical influences, fostering a shared appreciation for music and potentially leading to recommendations for future listening experiences.
47. What’s the most unusual habit you have?
Asking about someone’s most unusual habit encourages open conversation and reveals unique aspects of their personality and daily life.
48. If you could only eat one snack for the rest of your life, what would it be?
It invites exploration of flavors and indulgences, fostering a lighthearted exchange and potential shared enthusiasm for snacking between you and your date.
49. What’s the strangest thing you’ve ever seen someone do in public?
It leads to discussions about memorable encounters, cultural differences, and the unpredictability of public spaces, fostering a lighthearted exchange and potential shared experiences between you and your date.
50. If you could have any celebrity follow you on social media, who would it be?
Asking this question allows you to understand your date’s interests and influences, giving insight into their celebrity crushes or role models, and potentially sparking discussions about their favorite movies, music, or causes they support.
51. What’s the silliest thing you’ve ever done to impress someone?
Inquiring about silly attempts at impressing someone offers a glimpse into your date’s sense of humor and willingness to take risks in social situations, leading to shared laughter and perhaps tales of endearing or cringeworthy moments from past experiences.
52. If you could be any Disney character, who would you be?
This question taps into nostalgic feelings and reveals your date’s childhood favorites or aspirational qualities they admire in fictional characters, potentially leading to discussions about themes of heroism, bravery, and love in Disney stories.
53. What’s the most embarrassing thing that’s ever happened to you while traveling?
Asking about embarrassing travel experiences creates opportunities for amusing anecdotes and shared stories, fostering a sense of camaraderie and understanding about the unpredictable nature of travel.
54. If you could only eat one dessert for the rest of your life, what would it be?
Inquiring about favorite desserts reveals your date’s sweet tooth and culinary preferences, sparking conversations about indulgent treats and memorable dining experiences.
55. What’s the weirdest dream you’ve ever had about someone else?
This question delves into the realm of dreams and subconscious thoughts, inviting your date to share intriguing or bizarre dream scenarios and leading to discussions about symbolism, interpretation, and the mysteries of the mind.
56. If you could only watch one genre of movies for the rest of your life, what would it be?
Asking about preferred movie genres sheds light on your date’s cinematic tastes and entertainment preferences, opening avenues for discussions about favorite films, directors, and storytelling styles.
57. What’s the most unusual dream you’ve ever had?
This question prompts discussions about the surreal and fantastical elements of dreams, allowing your date to share intriguing or perplexing dream experiences and potentially leading to reflections on the subconscious mind.
58. If you could only speak one language for the rest of your life, which would it be?
Inquiring about preferred languages reveals your date’s linguistic interests and cultural connections, fostering discussions about travel, communication, and multicultural experiences.
59. What’s the most embarrassing thing you’ve ever done while drunk?
Asking about embarrassing drunk experiences encourages open conversation and humorous anecdotes, fostering a sense of shared vulnerability and understanding about the unpredictability of social situations.
60. If you could have any fictional creature as a pet, what would it be?
This question invites imaginative exploration of mythical creatures and reveals your date’s fantasy interests and whimsical preferences, potentially leading to playful discussions about magical creatures and legendary beasts.
Read the blog post: 7 Signs You Will Never Get A Girlfriend
More silly first date questions to ask your date for a night of laughter
61. What’s the weirdest dream you’ve ever had that you can’t explain?
Asking about unexplainable dreams invites your date to share mysterious or surreal experiences, fostering conversations about the subconscious mind and the mysteries of dreaming.
62. If you could only eat one type of candy for the rest of your life, what would it be?
Inquiring about preferred candy reflects your date’s sweet tooth and indulgent cravings, sparking discussions about flavors, textures, and childhood memories associated with their favorite confections.
63. What’s the most unusual thing you’ve ever seen at a party?
Asking about unusual party sightings prompts amusing anecdotes and reveals your date’s experiences in social settings, potentially leading to shared laughter and humorous stories about memorable gatherings.
64. If you could have any accent, which would you choose?
Inquiring about desired accents reflects your date’s linguistic interests and cultural connections, fostering discussions about travel, language learning, and the allure of different dialects.
65. What’s the most embarrassing thing you’ve ever done in front of a crush?
Asking about embarrassing moments with crushes invites vulnerability and reveals humorous or endearing anecdotes from your date’s romantic endeavors, potentially leading to shared laughter and relatable experiences.
66. If you could only eat one type of fruit for the rest of your life, what would it be?
Inquiring about preferred fruits reflects your date’s dietary preferences and nutritional interests, sparking discussions about flavors, health benefits, and culinary versatility.
67. What’s the weirdest thing you’ve ever found in your pocket?
Asking about strange pocket discoveries prompts amusing anecdotes and reveals your date’s experiences with random belongings, potentially leading to shared laughter and entertaining stories about unexpected finds.
68. If you could only watch one TV channel for the rest of your life, what would it be?
Inquiring about preferred TV channels reflects your date’s entertainment tastes and viewing habits, sparking discussions about favorite shows, genres, and media consumption habits.
69. What’s the most unusual dream you’ve ever had that you wish you could forget?
Asking about unforgettable yet unsettling dreams prompts introspection and reveals your date’s experiences with vivid or haunting dreamscapes, potentially leading to discussions about symbolism, fears, and the power of the subconscious mind.
70. If you could only wear one type of clothing for the rest of your life, what would it be?
Inquiring about preferred clothing reflects your date’s fashion preferences and personal style, sparking discussions about comfort, self-expression, and sartorial choices.
71. What’s the most embarrassing thing you’ve ever done on social media?
Asking about embarrassing social media moments prompts discussions about digital footprints and online interactions, potentially leading to reflections on privacy, self-image, and the influence of social platforms.
72. If you could have any animal as a sidekick, what would it be?
Inquiring about desired animal companions reflects your date’s whimsical interests and preferences for fictional partnerships, sparking imaginative discussions about loyalty, adventure, and camaraderie.
73. What’s the weirdest dream you’ve ever had about someone famous?
Asking about unusual dreams involving celebrities prompts amusing anecdotes and reveals your date’s experiences with surreal encounters in dreamland, potentially leading to discussions about fame, fandom, and the subconscious mind.
74. If you could only eat one fast food item for the rest of your life, what would it be?
Inquiring about preferred fast food items reflects your date’s indulgent cravings and culinary guilty pleasures, sparking discussions about flavors, cravings, and dining experiences.
75. What’s the most unusual thing you’ve ever seen in nature?
Asking about unusual natural sightings prompts discussions about wildlife encounters and outdoor adventures, potentially leading to shared appreciation for the wonders of the natural world.
76. If you could have any accent, what would it be?
Inquiring about desired accents reflects your date’s linguistic interests and cultural connections, fostering discussions about travel, communication, and multicultural experiences.
77. What’s the most embarrassing thing you’ve ever done at a concert?
Asking about embarrassing concert experiences prompts entertaining anecdotes and reveals your date’s experiences in live music settings, potentially leading to shared laughter and memorable stories about concert mishaps.
78. If you could only eat one type of pasta for the rest of your life, what would it be?
Inquiring about preferred pasta reflects your date’s culinary preferences and comfort food cravings, sparking discussions about flavors, sauces, and Italian cuisine.
79. What’s the weirdest dream you’ve ever had that came true?
Asking about dreams that came true prompts discussions about premonitions and deja vu experiences, potentially leading to reflections on intuition, coincidence, and the mysteries of the subconscious mind.
80. If you could have any mythical creature as a pet, what would it be?
Inquiring about mythical pets reflects your date’s whimsical interests and preferences for fantastical companions, sparking imaginative discussions about legendary creatures and magical adventures.
81. What’s the most embarrassing thing you’ve ever done on a dare?
Asking about embarrassing dare experiences prompts entertaining anecdotes and reveals your date’s experiences with playful challenges, potentially leading to shared laughter and humorous stories about daring exploits.
82. If you could only listen to one podcast for the rest of your life, what would it be?
Inquiring about preferred podcasts reflects your date’s audio interests and intellectual curiosities, sparking discussions about topics of interest, storytelling formats, and digital media consumption habits.
83. What’s the weirdest thing you’ve ever found in your fridge?
Asking about unusual fridge findings prompts amusing anecdotes and reveals your date’s experiences with culinary surprises and unexpected discoveries, potentially leading to shared laughter and entertaining stories about kitchen adventures.
84. If you could have any job for a day, what would it be?
Inquiring about desired temporary jobs reflects your date’s career interests and aspirations, sparking discussions about dream professions, work-life balance, and personal fulfillment.
85. What’s the most embarrassing thing you’ve ever done in front of your parents?
Asking about embarrassing moments with parents invites vulnerability and reveals humorous or endearing anecdotes from your date’s family interactions, potentially leading to shared laughter and relatable experiences.
86. If you could only eat one type of bread for the rest of your life, what would it be?
Inquiring about preferred bread reflects your date’s culinary preferences and dietary habits, sparking discussions about flavors, textures, and baking traditions.
87. What’s the weirdest thing you’ve ever found in your car?
Asking about unusual car discoveries prompts amusing anecdotes and reveals your date’s experiences with unexpected belongings and surprising clutter, potentially leading to shared laughter and entertaining stories about road trip adventures.
88. If you could have any animal as a best friend, what would it be?
Inquiring about desired animal friendships reflects your date’s whimsical interests and preferences for loyal companions, sparking imaginative discussions about loyalty, companionship, and animal instincts.
89. What’s the most embarrassing thing you’ve ever done in front of your boss?
Asking about embarrassing moments at work invites vulnerability and reveals your date’s professional experiences and interpersonal skills, potentially leading to shared laughter and relatable stories about workplace blunders.
90. If you could only watch one YouTube channel for the rest of your life, what would it be?
Inquiring about preferred YouTube channels reflects your date’s online interests and digital entertainment preferences, sparking discussions about content creators, online communities, and media consumption habits.
Additional hilarious dating questions to ask on a first date
91. What’s the weirdest thing you’ve ever found in your bed?
92. If you could have any talent, what would it be?
93. What’s the most embarrassing thing you’ve ever done in a restaurant?
94. If you could only eat one type of potato for the rest of your life, what would it be?
95. What’s the weirdest thing you’ve ever found in your closet?
96. If you could have any animal as a roommate, what would it be?
97. What’s the most embarrassing thing you’ve ever done in front of a celebrity?
98. If you could only drink one beverage for the rest of your life, what would it be?
99. What’s the weirdest thing you’ve ever found in your purse/wallet?
100. If you could have any animal as a mode of transportation, what would it be?
101. What’s the most embarrassing thing you’ve ever done on a video call?
102. If you could only eat one type of cheese for the rest of your life, what would it be?
103. What’s the weirdest thing you’ve ever found in your bathroom?
104. If you could have any animal as a butler, what would it be?
105. What’s the most embarrassing thing you’ve ever done at a party?
106. If you could only eat one type of nut for the rest of your life, what would it be?
107. What’s the weirdest thing you’ve ever found in your backyard?
108. If you could have any animal as a fashion accessory, what would it be?
109. What’s the most embarrassing thing you’ve ever done on a plane?
110. If you could only eat one type of cereal for the rest of your life, what would it be?
111. What’s the weirdest thing you’ve ever found in your kitchen?
112. If you could have any animal as a personal trainer, what would it be?
113. What’s the most embarrassing thing you’ve ever done in a movie theater?
114. If you could only eat one type of soup for the rest of your life, what would it be?
115. What’s the weirdest thing you’ve ever found in your backyard?
116. If you could have any animal as a therapist, what would it be?
117. What’s the most embarrassing thing you’ve ever done on a rollercoaster?
118. If you could only eat one type of sandwich for the rest of your life, what would it be?
119. What’s the weirdest thing you’ve ever found in your attic?
120. If you could have any animal as a roommate, what would it be?
***
From sharing embarrassing moments to unraveling dreams and preferences, these questions not only break the ice but also invite genuine exchanges, unveiling layers of personality and sparking memorable conversations that lay the foundation for deeper connections in budding relationships.
