Say hello to 100 date night questions, a perfect mix of random, funny, and wonderfully weird conversation starters.


If stale and uninspired questions make you cringe with boredom and you want to inject some fun, creativity, and quirkiness into your date night conversations, then you’ve come to the right place, amigo!


Feast your gorgeous eyes on the below 100 date night questions that will get you talking, laughing, and maybe even slightly blushing. From hypothetical scenarios to philosophical musings, from nostalgic reminiscing to silly hypotheticals, these date night questions are designed to help you have more fun. Because you should always remember to have fun!


Feel free to use these date night questions outside of date night. They also make great conversation starters for dinner parties and family gatherings! All the new and beautiful things you can learn about your partner, friends, and family with these wonderfully weird conversation starters are amazing.


Whether you’re looking to break the ice, deepen your connection, or just have a good time. Let’s dive into the date night questions!


100 Date Night Questions (1-50)

Print or copy and paste the below date night questions:


Do you have a hidden talent?


What reality TV show do you think you would thrive on?


Would you consider a polyamorous relationship?


Have you ever broken the law?


What’s the closest you’ve ever come to being arrested?


What was the best thing about leaving home?


Have you ever spent a night in jail?


What’s your biggest insecurity?


If you could have any superpower, but it had to be completely useless, what would you choose?


What’s your worst habit?


What’s one thing you only do when you’re alone?


What do you think aliens might look like?


What was the last food you binged on?


Have you ever stolen anything?


Whose calls do you avoid?


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


What five things would you take with you during a zombie attack?


What would it be if you could commit any crime with no repercussions?


How do you feel about sharing your passwords with your partner?


Have you ever cheated?


What’s a relationship dealbreaker for you?


What is your biggest fantasy?


What are you grateful to your parents for?


Of anyone in the world, who do you want to trade lives with?


How would you rate your looks on a scale of 1 to 10?


Do you believe in second chances?


Name one bad quality you can’t tolerate in a partner.


Would you break up with your partner for 10 million dollars?


What is your biggest fear?


Do you pee in the shower?


When was the last time you wet the bed?


If money was no object, what would you buy?


What’s the last lie you told?


What is the most embarrassing thing that you’ve done for a friend?


What is your definition of a perfect life?


What childish thing do you still enjoy?


Have you ever tasted a booger?


What topic are you tired of hearing about?


Do you find yourself judging others? If so, in what way?


What personality trait do you admire the most and why?


You’re in a public restroom, and you just went number 2. You realize your stall is out of toilet paper. What do you do?


Would you say you are more introverted or extroverted? Explain why.


You’re at a friend’s house for dinner, and you accidentally spill red wine on their carpet. Do you tell them and risk ruining the mood of the evening, or do you wait until the end of the night and hope they don’t notice, but risk the stain setting in?


Who is your hero? Why?


What was the worst purchase you’ve ever made?


What is your go-to karaoke song?


What is the weirdest thing that your family does together?


If you could pick any animal in the world as a pet, what would you choose?


What is a dream you still have yet to accomplish?


What is the weirdest thing about you?

100 Date Night Questions Wonderfully Weird Conversation Starters Blog (1)

100 Date Night Questions (51-100)

Here are another 50 date night questions!


What is the weirdest thing that has ever happened to you?


Recount an embarrassing memory.


What’s your favorite hobby?


A genie grants you 3 wishes. What would you wish for and why?


Is doing what you’re doing now what you always wanted to do growing up?


What do you consider your best physical feature?


What is the sexiest, non-sexual thing your partner does?


Name the one lousy quality you can tolerate in a partner.


What trait do you envy in others?


What is usually the first thing you think about when you wake up?


How do you wish to be remembered?


What is something you despise that everyone else seems to love?


What’s your favorite smell in the world?


When I’m drunk, I like to eat…


How would you describe me to someone that has never met me?


What do you think you spend too much money on?


If you could discover one thing about the future, what would it be and why?


What’s an unpopular opinion you have that goes against the status quo?


Would you change your name? What to?


What creeps you out the most?


You’ve won 1 million dollars in the lottery. What is the first thing you do?


Which of your character traits adds the most value to the world? Why?


What’s your ideal vacation?


How important is it to you to love your job? Why?


What food could you not live without?


What would your bestie say is your best quality?


What do you think happens after death?


If you could be told with certainty the date of your passing, would you want to hear it?


If immortality was a possibility, would you want it? Why?


If you could decide how you die, what would you pick?


Out of the negative emotions of jealousy, greed, hate, and anger, which d you think affects you the most?


Recount a moment of awe.


Do you think time travel will ever exist?


Do you think we are here randomly, or is there a greater purpose?


Out of the positive emotions of enthusiasm, compassion, initiative, and positivity, which is your biggest strength?


What is your most annoying quality as a partner?


Are you a people pleaser? Why?


Who would it be if you had to cut one friend out of your life?


Name five things you would do if you could be invisible for a day?


Who is the one person you constantly stalk on social media?


What’s the longest you’ve ever gone without taking a shower?


Who is your celebrity crush?


What do you think the meaning of life is?


Do you think some people are born evil, or does it depend on their environment?


What’s something that people misunderstand about you?


What’s something you have to do every day?


You meet a time traveler from 200 years in the future. What questions do you ask?


What’s your biggest pet peeve?


What has been the best phase in your life up until now?


Who would you invite first as a guest if you had your own talk show?


Enjoy Your Next Date Night With These 100 Date Night Questions

Great conversation is the key to epic dates, and these 100 date night questions are guaranteed to help you and your partner connect in new and exciting ways.


By exploring hypothetical scenarios, sharing personal stories, and delving into philosophical musings, you’ll learn more about your lover and gain a deeper understanding of yourself and your own perspectives too!


So next time you find yourself entering the world of stale and uninspiring conversation, don’t be afraid to whip out these date night questions and get ready to learn lots of new things about your lover! Who knows what fascinating discussions and meaningful connections await you?


Get These Date Night Questions as Cute Printable Conversation Cards on my Etsy Store

If you liked these date night questions, you can buy a printable card version here. Get your Printable Conversation Cards TODAY!

100 Date Night Questions Wonderfully Weird Conversation Starters Blog
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