150 + Funny First Date Questions

If you’re tired of the same old small talk and want to break the ice in a fun and lighthearted way, consider asking some funny first-date questions. Not only will they help you get to know your date better, but they’ll also inject some humor and playfulness into your conversation. In this article, we’ll share some of our favorite funny first-date questions that are sure to get the conversation flowing and help you both have a great time. So, get ready to laugh and let’s dive in!


I’ve separated the list into three parts to make things simpler. You may use humorous icebreakers to get the discussion going, humorous follow-up questions to make you feel more at ease as the date progresses, and flirtatious follow-up questions when things are really going well.

I hope the list proves to be helpful.

Funny First Date Questions To Use As Ice Breakers

These inquiries are the ideal icebreakers to start a discussion and get to know your date. You’ll have a lot of luck with these amusing first-date questions since most individuals enjoy talking about themselves. Here are our top 10 –

  1. “Describe yourself in one emoji. I’ll go first: 🙋”
  2. “What’s your favorite thing to do on weekends?”
  3. “Do you know your enneagram type?”
  4. “What’s the best vacation you’ve ever been on?”
  5. “What’s your favorite conspiracy theory?”
  6. “What’s your favorite thing about your job?”
  7. “What’s your favorite thing about your city?”
  8. “What’s your favorite thing about your family?”
  9. “What’s your favorite thing about yourself?”
  10. “What’s your favorite thing about your pet?”

Bonus –

  • What subject would you cover in your TED talk?
  • When you were a child, which candy was your favorite?
  • What topic never gets old in conversation for you?
  • Have you ever met a famous person?
  • What do you like to cook the most?
  • Where would you go on vacation if you could go anywhere?
  • Which do you prefer, cats or dogs?
  • What is your preferred late-night treat?
  • What would you do if you suddenly got $1,000,000 today?
  • Which would you choose, the city or the country?
  • What was your worst job to date?
  • Which movie did you think was the finest recently?
  • What was the worst thing you ever did on a date?
  • Is your home now cleaner than your car?
  • What was the funniest thing you saw recently?
  • Do you think in the paranormal?
  • When you were a child, what did you want to be?
  • What is the finest piece of advise you have ever heard?
  • Which of your past dates was the worst?
  • What nation would you relocate to if you had to?
  • What occupy your time the most?
  • When was the last time you celebrated Halloween in costume?
  • What television series or movies are your guilty pleasures?
  • What do you feel proud of but never have a reason to share?
  • What about you most people find ordinary?
  • Which of your past dates was the best?
  • What about you would I find hard to believe?
  • What kind of house would you like to have?
  • What sports did you play in high school or junior high?
  • What kind of workout do you prefer?
  • Who was the greatest live performer you’ve ever seen?
  • How would you sum up your youthful self?
  • What irritates you about people the most?
  • What is the silliest thing you have witnessed in the past 12 months?
  • How would you sum up your life in one sentence?
  • What brought you two together?
  • What is your all-time favourite book?
  • Who is your favourite celebrity?
  • Which of your past vacations was the best?
  • Which place do you choose for a vacation—near the seaside or in the mountains?

Funny First Date Questions To Ask When You Feel More At Ease

\It’s appropriate to ask the important questions after the date is well going and you feel more at ease. With the help of these humorous first date questions, you may demonstrate your sense of humor and make your date laugh.

  • What’s the most humiliating outfit you’ve ever worn?
  • What is something you’ve accomplished that you think everyone should do?
  • What would you most like to do illegally?
  • What do you believe you are knowledgeable about but are probably not?
  • When you hear a certain song, do you constantly sing along?
  • What would the name of your rapper be?
  • Which superpower would you like to have the most?
  • What components make the ideal pizza?
  • Which animal has the most entertaining noises?
  • What annoys you the most about the other sex?
  • What did you adore that turned out to be a terrible waste of money?
  • What would you do with your time if you didn’t have to work?
  • What would the name of the film about your life be called?
  • What would be your one-sentence summary of social media?
  • Which of your past compliments stands out as the best?
  • What would you select if you could only eat one meal for the rest of your life?
  • What unusual taste combination do you truly enjoy?
  • What famous person would you be if you could be for a day?
  • What would you want if you were given the chance to make three wishes?
  • What would the signs be if you had an illness named after you?
  • Which person gave you the worst present you’ve ever received?
  • What karaoke song is your favorite?
  • What has ever happened to you that you find strange?
  • Whom would you pick if you could switch places with anyone in the world?
  • What does the majority of the population find simple for you?
  • Which one of your jokes is the worst?
  • What might I say or do to impress your parents the most?
  • Are you a morning person or a night owl?
  • How long have you ever gone without sleeping?
  • What falsehood would you like to create?
  • When you arrive home, what do you do first?
  • What animal do you believe would be the most awesome if it could talk?
  • Which would you prefer: being able to just yell or whisper?
  • What components make the ideal burger?
  • If you could spy on anyone without being discovered, who would it be?
  • What was the strangest thing you’ve ever witnessed in a person’s home?
  • What words of wisdom would you impart to a 5-year-old you?
  • Which would you choose: the capacity to teleport or fly?
  • Which day of your life would you like to relive if you could?
  • What was the funniest practical joke you ever played on someone?
  • What would be your swan song?
  • Which dish was the worst you’ve ever had?
  • Which appliance would you choose to live without permanently if you had to?
  • What odour is the worst there is?
  • What was the most priceless item you ever damaged?
  • What do you think your friends would presume you did if you were arrested for a crime?
  • What would you do if there were no repercussions to get fired?
  • Have you ever been asked to leave a bar or restaurant?
  • What outfit would you never wear outside your home?
  • Which Wi-Fi name do you think is the best?
  • What insignificant issue aggravates you more than it ought to?
  • Before you gave it a try, what did you consider stupid?
  • What would be the worst possible manner to pass away?
  • What has been your most bizarre action?
  • What does everyone do that makes them appear foolish?
  • Which age would you like to remain at if you could do so?
  • What has been your most humiliating moment?

First Date Questions When The Date Is Going Good

It’s time to turn up the heat a little and ask some more flirtatious and humorous questions if you and your date are clicking. While none of them are overtly flirtatious, your date will know you’re interested.

  • Do you consider yourself to be a good flirt?
  • Which celebrity would you most want to have a free pass to bed?
  • What is your go-to icebreaker?
  • Have you ever purchased underwear to make a man feel good?
  • What additional items come with your action figure?
  • What do you believe attracts men and women to you the most?
  • Are you being good or bad?
  • Have you ever experienced intense jealousy?
  • Which romantic film have you ever seen?
  • What clothing item do you like to wear to bed?
  • What shade of underpants are you currently sporting?
  • What is an exciting activity you have never tried but would love to?
  • How frequently do you gaze at your behind in the mirror?
  • What transpired on your most recent unsuccessful date?
  • What was the funniest thing you ever did while under the influence?
  • What about your bedroom is the most embarrassing?
  • Which of your sexual dreams was the strangest?
  • What’s the worst pick-up line you’ve ever been subjected to?
  • Have you ever left the house without your undies?
  • Where do you itch the most?
  • What do you consider to be the ideal date?
  • Which would you choose: engaging conversation or excellent sex?
  • Which adjective do you prefer, sexy or cute?
  • Consider we a compatible couple?
  • What did you think of me at first?
  • Which present has been the hottest you’ve ever received?
  • Has anybody ever discovered you unclothed?
  • Have you ever hurt someone else’s feelings?
  • Which of your physical traits do you believe is the best?
  • Do you like long, warm hugs more than intense kisses?
  • Do you think there are soul mates?
  • What is the name of the hottest girl?
  • Would you consent to having your lover choose your outfit?
  • How did you feel during your first kiss, and who was it with?
  • What was the naughtiest thing you ever did?
  • Have you ever had a heartbreak?
  • Do you consider yourself a good secret keeper?
  • What one words would you use to sum up who I am?
  • What has been your most outrageous act of love?
  • What is the most critical attribute a man or woman should possess that isn’t physical?
  • Where do you like to get massaged the most?
  • When was the last time you were in love?
  • What most arouses your interest?
  • What is anything unique about you that you haven’t shared with anybody else?
  • Which of your first dates was the worst?
  • What was the most foolish thing you ever did because of love?
  • If your parents set you up with someone, would you go on a date with them?
  • What is one aspect of your physique that, if you could, you would change?
  • Flirting is it cheating?
  • What distinguishes a man or woman as attractive?
  • What is the greatest lie you’ve ever been told by a date?

A Little Tip

The most crucial element is to only sometimes utilize these queries. Choose your favorites and have them handy for when you find yourself at a loss for words. You want the conversation to flow as effortlessly as possible while on a date. Your date won’t enjoy the conversation if you sound robotically running through a list of questions; instead, they’ll feel questioned.

Therefore, if you’re having trouble starting a conversation, ask one of these questions and see where it leads.

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