Funny First Date Questions: The Key to Great Conversations

Dating can often feel like a nerve-wracking interview. You want to present yourself honestly and interestingly, but you also need to entertain your date. Breaking the ice can be a challenge, but with the right funny first date questions, you can elevate your date, get a laugh, and get to know each other better.

A Few Ice Breakers

  • What’s the most embarrassing song on your playlist?
  • What’s your absolute favorite meme?
  • What song would you sing at karaoke if you absolutely had to participate?
  • What’s the best (and worst) Halloween costume you’ve ever worn?
  • If you had to give a TED Talk on any subject without preparation, what would it be?
  • What’s the most random and/or embarrassing thing you’re afraid of?
  • What was your worst or weirdest first date?
  • What’s the weirdest gift you’ve ever received or given?
  • What movie can you quote all the lines from?
  • Does pineapple belong on pizza?

Questions About Their Childhood

  • Who was your first celebrity crush?
  • What’s the worst fashion trend you’ve ever participated in?
  • Have you ever participated in a flash mob or other social media challenge?
  • How old were you when you stopped believing in Santa Claus and the Tooth Fairy?
  • Have you ever had a crush on a cartoon character, and who was it?
  • Who is the craziest member of your family?
  • What was your favorite show as a kid?
  • What was your favorite show as a teenager?
  • What was your first concert and your best concert?
  • What TV show best describes your family dynamic?

Questions About Them at School or at Work

  • What job are you totally unqualified for that you think you would still be good at?
  • Which Breakfast Club character were you most like in high school?
  • What’s the worst and the best reasons you’ve ever called out of work for the day?
  • Would you still work if you won the lottery, or would you quit immediately?
  • What’s the most unnecessary lie you’ve ever included on your resume?
  • What do you actually do for a living vs what people think you actually do?
  • Who would be the best and worst coworkers to be stuck in an elevator with for a day?
  • What theme song should play when you walk into work or school?
  • What would be your job during an apocalypse?
  • What part of your work or school day is absolutely, weirdly sacred to you?
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Questions About Love and Dating

  • Who would you Marry, Kiss, and Kill from the cast of The Office?
  • What celebrity couple is your most favorite? Which one is your least favorite?
  • What emoji best describes you if you could only pick one?
  • What emoji do you irrationally hate and never use?
  • What’s the weirdest thing that’s ever happened to you on a date?
  • What’s the worst pickup line you’ve ever heard (or used)?
  • What pet names do you irrationally hate?
  • What is your most annoying habit?
  • What is the craziest thing you’ve ever done for love?
  • If you had to live with one ex for the rest of your life, which one would it be? If it’s absolutely none of them, how would you fake your death and where would you go?

Other Questions

  • What Taylor Swift era are you in if you had to pick one?
  • What is your favorite weird food combination?
  • What is the nerdiest thing about you?
  • What’s one thing about you that is totally basic?
  • If you could only have one social media app, which one are you choosing and why?
  • Which character on Schitt’s Creek speaks to you the most, spiritually?
  • What book do you say you’ve read but have never actually picked up?
  • What movie does everyone else love that you’ve either never seen or completely hate?
  • Which fandom do you think is the most ridiculous?
  • Do you prefer Team Peeta or Team Gale?
  • What’s the weirdest recurring dream you’ve ever had?
  • Which celebrities would make your Hall Pass list?
  • Which Hogwarts House would you be sorted into?
  • Which super villain do you most vibe with if you had to choose?
  • What childhood cartoon would you most want to see a live-action remake of now?
  • Which celebrity should play you if your life was a movie?
  • What song would you want to play if you were being auctioned off for a date night for charity?
  • What movie quote do you use most often?
  • If you could eliminate one random band or artist from history, who would it be and why?
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A Few More Questions

  • Which condiment do you irrationally and completely hate?
  • If your pet gave you a name, what would it be?
  • Which celebrity couple’s relationship are you overly invested in?
  • If there was a reality show about your life, what would it be called?
  • A friend calls and asks you to help them hide a body—which friend is on the phone, and would you help them out?
  • Would you rather have the Sunday scaries or a case of the Mondays?
  • If you could only read one author for the rest of your life, who would you choose?
  • What’s a television series you’ve binged countless times?
  • What is the weirdest thing you bought or learned during the pandemic?
  • Would you rather be a werewolf or a vampire?
  • What would your stripper name be if you had to choose right now?
  • Have you ever been told you look like a celebrity? Which one?
  • If your DJ name was a combination of your first pet’s name and your favorite snack, what would it be?
  • What fact about your past automatically makes you sound ancient?
  • Would you rather fight dinosaurs or zombies in hand-to-hand combat?
  • Have you ever had an alien or UFO encounter?
  • Have you ever seen a ghost or been in a genuinely haunted house?

Don’t Make It (Too) Weird: Tips for Enjoying a First Date

While these funny questions can help break the ice, it’s essential to read the room and avoid making the conversation too weird or uncomfortable. If your date doesn’t have an answer or isn’t enjoying a particular question, let it go and focus on other topics.

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To make the first date more enjoyable, be creative with your plans. Choose a fun and unique activity that allows for conversation to flow naturally. Consider shared interests and think outside the box to create a memorable experience.

Remember to leave your expectations at home and approach the date as an opportunity to get to know someone new. Keep the conversation respectful and kind, even if it doesn’t lead to a romantic connection. Dating is about having a good time and learning about each other.

So, armed with these funny first date questions and these tips, you can now approach your next date with confidence and the intention to have a great time. Who knows, you might even find a genuine connection amidst the laughter.


To find more unique and engaging date ideas, visit Six Minute Dates. Happy dating!