In case no one’s informed you, we’re currently living through a dating crisis in which some folks have gotten, well, not so great at asking questions on dates. Seriously—it’s a pandemic. I’ve honestly lost count of the number of friends who’ve said “it went okay but they didn’t really ask me anything about myself…” when recapping a recent date. So if you’ve ever been on the receiving end of “Is there anything you want to know about me?”, then this list of fun date questions is for you. But honestly, it’s for anyone who’s on a date and wants to get to know the person on the other side—which is, honestly, the whole point of going on dates to begin with.
Whether it’s a virtual chat or a walk in the park, first dates can be nerve-wracking. But they should also be fun. Having some fun questions prepped and ready to go is a great way to take some of the pressure off and actually laugh. Lucky for you, the ones below were designed to fulfill both purposes: To help you learn more about the person and laugh together. Remember: Humor is sexy, and it’s a great way to bond. Damona Hoffman, host of the Dates & Mates podcast, calls it one of the best ways to connect with people and ease tension, whether that means breaking the ice on a slightly awkward first date, or deepening your bond with friends and loved ones.
That doesn’t mean you have to have a tight-ten standup routine memorized before every first date or friend hang, though. According to dating coach Alexis Germany, the key to being funny is not trying too hard. Trust your own sense of humor—whether you like puns, dad jokes, or topical quips about reality TV shows—and lean into it. Just not, like too hard, ya know?
So without further ado, here are 200 (count ‘em!) fun questions to ask on your next date. Get ready to full-body laugh all night.
- What’s the most basic thing about you?
- What’s the most embarrassing song you unironically love?
- What’s your funniest misheard song lyric? “Gotta love those Starbucks lovers.”
- What kind of drunk are you? Chatty over-sharer? Sobbing disaster? Messy babe who lives for chaos?
- Which Taylor Swift era are you?
- What’s your worst quality according to astrology that is 100 percent true about you? Type A Capricorn? Weepy Pisces? Spill.
- What’s your go-to sadness meal? Dry cereal out of the box with your hands, anyone?
- What’s the most unhinged thing you’ve done this year?
- If you had to change your name, what would you change it to?
- If you had to change my name, what would you change it to?
- What’s the worst condiment? My mayo haters live for this one.
- Most absurd social media challenge you participated in?
- Who’s your most unhinged family member?
- If you got famous, what would you be famous for?
- What’s something you’re legitimately bad at?
- What’s one thing you hope your parents never find out about you?
- Do you believe in ghosts?
- Would you rather aliens or robots take over the world?
- Which social media platform needs to die?
- If you got canceled what would you get canceled for?
- What’s the most cringe thing you’ve ever posted on social media?
- If you could start a rumor about yourself, what would it be?
- Who’s the worst celebrity couple?
- Which celebrity do you think would actually be a good president?
- Which celebrity do you think would be the actual worst president?
- Where’s the worst place to get broken up with?
- What’s your go-to dating app opener?
- Do the rats run this city?
- If you could only listen to one song for the rest of your life, what would it be?
- Which celebrity couple will be the next to break up?
- Who would you pick to write your obituary?
- What celebrity would play you in a movie about your life?
- Which character from The Office are you?
- What’s a TV show literally everyone but you has seen?
- Let’s debate: Lana del Rey, Cancer or Gemini?
- What genre would a movie about your life be?
- Coke vs Pepsi?
- Who’s your problematic fave?
- Which horror movie archetype would you be?
- What’s the most overrated sex position?
- What’s the most underrated sex position?
- Which SATC character are you?
- If you got arrested, what crime would you have committed?
- Who’s your celebrity hall pass?
- Who’s your most obscure celebrity crush?
- What’s your favorite meme of all time?
- What would your middle school crush think if they knew you now?
- Would you be friends with your middle school self?
- Would you still date your middle school crush today?
- What’s the weirdest thing you do when you’re alone?
- What’s the weirdest thing your roommates have ever caught you doing?
- Do you think you’re a good liar?
- What’s one job you’re totally unqualified for but are positive you could do anyway?
- What do you think your therapist would tell their friends about you?
- What do you think your boss tells their friends about you?
- If you could live in any decade other than this one, which would you pick?
- Who’s the most overrated celebrity right now?
- How would your third grade teacher describe you?
- What’s the most ridiculous thing you’ve ever cried over?
- You have to wear one of your past Halloween costumes for the rest of your life. Which one are you picking?
- You get to switch bodies with your ex for one day. What’s the first thing you’re doing?
- Have you ever gotten caught social media stalking someone?
- Be honest, how often do you social media stalk your exes?
- Who was the first celebrity you were obsessed with as a kid?
- If you were a cocktail, what would you be?
- Which streaming service could you not live without and which one needs to die?
- What’s the most embarrassing thing you’ve said or done while drunk?
- Would you rather be 15 percent more attractive or 50 percent smarter?
- What movie scene always makes you ugly cry?
- What's your go-to excuse to get out of plans?
- What’s your least favorite emoji?
- Which emoji best encapsulates your essence?
- How long did it take you to pass your driver's test?
- What was your worst subject in school?
- What’s the most cringe thing anyone has ever said to you on a dating app?
- Are you a sexy baby or a monster on the hill?
- Which Disney Princess do you think you could win against in a fight and which one would totally kick your ass?
- What was your pandemic hobby?
- What was the last thing you Googled?
- What’s something you learned recently that you were embarrassed you didn’t already know?
- Which would you rather reveal: Your porn search history or your Grubhub history?
- What would your presidential campaign slogan be?
- Who would be your running mate?
- Which historical figure would you most want to be?
- If you had to get stuck in an elevator with one of your exes, which one would you choose?
- If you could relive one year of your life, which one would it be?
- Who is your fictional character crush?
- Would you rather show your porn search history to your mom or your crush?
- What’s the worst dating app?
- Have you ever been banned from a dating app? If so, how’d it happen?
- Are you a Kindle convert or a hard copy loyalist?
- What was the first song/album you downloaded on your first iPod/iPhone?
- What was the most embarrassing song on your last Spotify wrapped?
- If you could design your own signature perfume, what would you call it?
- Taylor Swift, Beyoncé, or Rihanna: Who’s the best pop star of all time?
- Which one of Henry VIII’s wives would you rather be?
- What's the one podcast you'd love to be a guest on?
- Were you given any yearbook superlatives in high school? If not, which one *should* you have gotten?
- What’s your social media platform of choice?
- What’s your most irrational fear?
- What’s the longest you’ve ever gone without sleep?
- If you could switch lives with one person for a day, who would it be?
- Do you think anyone has you blocked or muted on Instagram?
- Which Kardashian/Jenner would you most want to trade lives with?
- Which early aughts reality show would you bring back?
- Are you pro-reboots or over them?
- What’s the weirdest rumor you’ve ever heard about yourself?
- What was your worst first date?
- What’s your go-to excuse to bail on plans?
- Are you usually relieved when plans get canceled, or disappointed?
- What was the last thing you lied about?
- Would you rather give up ice cream or pizza?
- What’s the cringiest Millennial trend/behavior that needs to be eliminated from this planet?
- What is the appropriate way to text someone “okay”?
- What band would you get back together if you could?
- What’s the weirdest gift you’ve ever received?
- What’s the weirdest gift you’ve ever given?
- Have you ever crashed a wedding?
- Whose wedding would you object at?
- What was your funniest prank call experience?
- What was the weirdest thing you did for fun as a kid?
- What’s your weirdest turn-on? Dudes who keep their glasses on during sex? Just me?
- Would you rather give up caffeine or sugar?
- Diet Coke or Coke Zero?
- How long did your longest game of Monopoly last?
- What was your most regrettable impulse buy?
- Which Mean Girls character most closely embodies your high school self?
- Has anyone ever walked in on you masturbating/having sex?
- What personal hygiene thing are you low-key kinda lazy about?
- What do you lie to your doctor about?
- What’s a lie you told your parents that you got away with?
- What’s the most trouble you ever got in as a kid?
- What’s one thing you’re a total pick-me about?
- What’s the best way to break up with someone?
- What’s one dating app cliché you’re sick of seeing in people’s profiles?
- You get to have your dream wedding for free, the only catch is: You have to wear your high school prom dress. Would you do it?
- What was the nerdiest thing about you as a kid?
- What’s the most intense thing you’ve ever done to make a crush or an ex jealous?
- Where’s the weirdest place you’ve ever had sex?
- What’s your go-to bagel order?
- What’s the cringiest drink someone can order at a bar?
- What’s a sex myth you believed as a kid?
- What’s the most embarrassing song on your sex playlist?
- What TV show do you think you could quote the most lines from?
- Once and for all, does pineapple belong on pizza?
- If you could change your astrology sign, which one would you pick?
- Why is it embarrassing to get caught taking a mirror selfie in public but not embarrassing to post that selfie on social media?
- What current slang term needs to be retired ASAP?
- Who’s one celebrity you irrationally dislike for literally no reason?
- What would you name your own signature flavor of Ben &Jerry’s?
- Do you think your favorite high school teacher would be proud of you?
- What’s the biggest lie you’ve ever told and gotten away with?
- What do you think your mom was actually like at your age?
- What’s your favorite question to ask on a first date?
- If you were a writer or performer, what would be your pen name or stage name?
- Who do you think you were in a past life?
- What's your most unpopular food take?
- What’s your worst habit?
- Where can someone usually find you at the party?
- Do you think you’re a good wedding guest?
- Who is your dream plus-one?
- If you could give yourself a nickname, what would it be?
- What’s something you don’t know how to do that most people do?
- What’s the most annoying thing people do at the gym?
- What’s one TV show you would love to guest star on?
- Would you let your friends set you up on a blind date?
- What would be the theme song to the sitcom of your life?
- What’s one movie adaptation that was actually better than the book?
- Would you rather have five more close friends or 1,000 more Instagram followers?
- If someone only saw your Spotify or Netflix accounts, who would they think you are?
- Would you rather be TikTok famous or win a Grammy?
- Would you rather win a Grammy or an Oscar?
- Would you rather win an Oscar or an Emmy?
- What’s your best dad joke?
- What was the first R-rated movie you ever saw? Who took you?
- What’s a word you pronounced wrong your whole life?
- Can you please tell me about your best worst school photo?
- What was your AIM screen name?
- What was the worst middle school fashion trend you participated in?
- What do you buy too much of but seem to never have enough of?
- What’s the cheesiest internet pop psychology advice that actually struck a chord with you?
- Does being an influencer sound like a dream job or a worst nightmare?
- What’s the best WiFi name you’ve seen?
- If you were an amateur wrestler/D-List superhero, what would your name be?
- What’s your go-to karaoke song?
- What’s a book you’ve never read but pretend to have read?
- What would your vanity license plate be?
- Be honest, how many hours a day do you spend on TikTok?
- What’s something that’s embarrassing, but shouldn’t be?
- What type of grocery store shopper are you?
- What’s the stupidest way you’ve ever hurt yourself?
- What was something you believed as a kid for way too long?
- What’s the stupidest lie you ever told as a kid?
- What is the weirdest thing about you that most people wouldn’t guess from looking at you?
- Socks on during sex: Yea or nay?
- How long do you wait to get up to pee when you’re watching a really good TV show?
- What’s the grossest food thing you’ve ever done?
- Have you ever been sexually attracted to a cartoon character?
- What would be the title of your memoir?
- The most pressing question of our time: Is a hot dog a sandwich?
