So, knowing a couple of funny dating app conversation starters can be a great way to break the ice — and melt the tension. Claudia Cox, relationship coach and founder of Text Weapon, says that. Look no further than Bristlr, a dating app and website for bearded men and the people who prefer facial hair. It started as a joke website, but now Bristle founder John Kershaw says the app has. Prepare to laugh as you read these 18 funny dating stories that will make you cringe with embarrassment. These Twitter revelations that can be added to the list of the “worst dates in history.”. We feel sorry for the girl. What a total jerk! No other words can describe him. We’re so glad it didn’t work out.
You know what they say, “if you can make a girl laugh, you can make her do anything.”
Okay, I’m just kidding, I don’t know if anyone actually says that and it’s definitely not true. But, there’s no denying that many women list ‘funny’ when asked for qualities they hope to find in a partner.
Perfect abs or a chiseled jawline may fade with time, but a good sense of humor will last and can make the sometimes mundane activities of coupledom fun and enjoyable in the long run.
When getting to know someone on a dating app, the same old small-talk questions might get old. But, you definitely want to make sure to ask questions, as many men sometimes fail to do so which can steer you towards bad date territory.
If you’re struggling to keep a conversation going, or just want to add some comic relief to the flirtation, here are 50+ funny questions to ask a girl to make her laugh.
The Top 50 Funny Questions to Ask a Girl to Make Her Laugh
- If you woke up invisible tomorrow, what’s the first thing you’d do?
Hopefully she doesn’t say, “go through your phone.”
- What’s your weirdest deal breaker?
Take notes.
- What’s the worst date you’ve ever been on?
Take notes here, too.
- What’s the best Halloween costume you’ve ever worn?
The answer to this question may also include a photo.
- What cartoon do you still like to watch?
You be the judge of whether adult cartoons (Family Guy, Simpsons, etc.) count or not.
- What’s your go-to drunk and/or hangover food?
Make sure to find out if your date drinks before asking this question.
- Who’s the first celebrity crush you’ve ever had?
Yes, cartoon characters count.
- What’s your zodiac sign and do you think it’s accurate?
Even if neither of you believe in horoscopes, this is a fun way to learn more about your date.
- Which fictional place would you love to visit?
Think Whoville, Narnia, Hogwarts, Willy Wonka’s Chocolate Factory, and the like.
- What’s a funny nickname from your past?
Like with most of these questions, be prepared to answer for yourself too!
- Would you rather have more money or more time?
This may not be funny per se, but it’s definitely interesting and could lead to a great conversation.
- What’s your go-to karaoke song?
Store this information for later.
- What’s the last meme you screenshotted?
Make sure to give her privacy when scrolling through her camera roll.
- What’s the worst job you’ve ever had?
Maybe you’ll get a funny story about her scooping ice cream for bratty kids or actually having to save someone as a teen lifeguard.
- If you were arrested and your family found out, what would they assume you had done?
Hopefully she doesn’t say murder!
- If your pet could talk, what do you think they’d say?
For obvious reasons, only ask this one if you know your date has a furry friend.
- When’s the last time you found yourself in a food coma?
This is a good way to potentially find out her favorite food for your next date.
- What fashion trend from the past did you refuse to participate in?
Ponchos? Low-rise jeans? Frosted tips?
- What fashion trend from the past do you regret participating in?
Photos or it didn’t happen.
- What song is your guilty pleasure as of late?
We all have one (or many).
- If your internal monologue suddenly became audible, how screwed would you be?
Dive deep into your date’s mindset.
- Would you be more or less likely to talk to me if I grew out my hair and put it in a man bun?
This is a cheeky way to find out more about your date’s taste in men.
- Would you be more or less likely to talk to me if I wore a gold chain?
Same as above.
- What’s the funniest conversation you’ve overheard?
If you live somewhere that has an “overheard page” (example: @overheardLA), you can ask her if she knows about that page and if she’s ever heard anything worthy of submission. Bonus points if you’ve seen something funny on the page that you can also share.
- If you were an animal, which would you be and why?
Or, ask her what animal you look like!
- What alcoholic beverage brings back bad memories?
Read the room and make sure you ask this in a lighthearted way. You’re aiming for a response like, “I can’t have vanilla Smirnoff because it’s all I drank freshman year of college.”
- Do you say “yes” or “no” more often in life?
This is a great way to learn more about a person, because hopefully they’ll explain their answer. And if they don’t, ask them to!
- If you could be a character on the last show you binge-watched, who would you be?
This is one of the funny questions to ask a girl to make her laugh that takes a standard first-date question and makes it a little more fun.
- What’s an incorrect assumption many people make about you?
This gives your date a chance to clear up any confusion and put her best foot forward.
- What’s an invention that you think they should’ve come up with by now?
Flying cars, time machines, those microwaveable meals from Spy Kids. The possibilities are endless.
- If you had your own cooking show, what would you make?
Feel free to take her answer, put on your best announcer voice, and act like you’re narrating her cooking show for her.
- If you were a man for a day, what’s the first thing you’d do?
This could lead to some interesting responses…
- What’s an unconventional trait that you find really sexy on a man?
Maybe she loves bald dudes or guys with eyebrow piercings? Or maybe she just is a sucker for a guy in a bow-tie. These are all great things for you to know.
- If you had to smell like a food for your entire life, which would you choose?
This is another great way to potentially find out her favorite foods.
- What’s the last thing you burst out laughing at?
If anything, this will give you a window into her sense of humor and let you know why she might not be laughing at your jokes yet.
- What’s something about me that you think is funny?
Women can be sassy, so don’t ask this if you’re not prepared to take it.
- When did you find out that Santa Claus wasn’t real?
This question is best asked around the holiday season to not appear super random.
- Would you eat worms for $1000?
Feel free to sub in worms for any somewhat-gross item nearby if you’re on a date.
- If you were on Jeopardy, which category would you excel at?
Here’s a way to get your date to show off what random facts she knows best.
- If you could be on any reality show or game show, which would you have the best chance at winning?
Funny Dating Apps
If she says Too Hot Too Handle, make sure to take things slow with her.
- Can you wink?
This is a question that should be asked in person so that you can both practice your best wink.
- Can you raise one eyebrow?
Similar to the above question, this makes for a silly activity on a date.
- What’s your most used emoji?
You’d be surprised how much you can tell about someone from their emoji usage.
- What’s the weirdest celebrity encounter you’ve had?
This can lead to a funny story, or let you know that your date was a 1D fangirl in a past life.
- If they were to make a movie about your life, what genre would it be?
Hopefully she doesn’t say horror.
- Did you have any posters of singers or bands in your room as a teen?
This is one of the funny questions to ask a girl that is way more exciting than, “what kind of music do you like?”
- Have you ever performed in a talent show?
A great way to find out if your date has any secret talents or is super shy.
- What’s your favorite form of potatoes?
This question works best when ordering off a menu that includes french fries.
- What’s something that’s always in your fridge?
We all know what a typical bachelor fridge looks like, but what about a bachelorette’s fridge?
Keep in mind that if you’re using these funny questions to ask a girl to make her laugh, you want to try to work them into a conversation. If you text her out of the blue with a question, it might seem a little random and disingenuous. Instead, try to work in an animal question when she’s already talking about her dog. Or, try question #26 after you’ve both ordered drinks at the bar.
Funny Dating Application
Whichever funny questions you end up using, I guarantee that your conversations will be better than the ones she has with most men she matches with on dating apps.
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Funny Dating Quotes to get you in the mood for a hot dude. Or dudess. These will put you in the right frame for the night game. Laughter is the best aphrodisiac.
Dating Quotes
Group 1
I’ve been on so many blind dates I should get a free dog.
- Wendy Liebman
Bisexuality immediately doubles your chances for a date on Saturday night.
- Woody Allen
What is a date, really, but a job interview that lasts all night? The only difference is there aren’t many job interviews where you’ll wind up naked.
- Jerry Seinfeld
Whenever I want a really nice meal, I start dating again.
- Susan Healy
Funny Dating Quotes
Group 2
On a date I wonder if there’s going to be any sex. And if I’m going to be involved.
- Garry Shandling
I went on a date recently and the guy took me horseback riding. That was kind of fun, until we ran out of quarters.
- Susie Loucks
My sister was with two men in one night. She could hardly walk after that. Can you imagine? Two dinners!
- Sarah Silverman
I went out to dinner with a Marine. He looked at me and said, “I could kill you in seven seconds.” I go, “I’ll just have toast then.”
- Margaret Smith
I asked this one girl out and she said, “You got a friend?” I said yes. She said, “Then go out with him.”
- Don Irreva
I dated a hypnotist once. She was the hottest, smartest, skinniest, funniest, kindest, most glamorous and sophisticated woman I’ve ever met.
- Kent Graham @KentWGraham
Funny Dating Quotes
Group 3
My father always said, “Be the kind they marry, not the kind they date.” So on our first date I’d nag the guy for a new dishwasher.
- Kris McGaha
I hate first dates. I made the mistake of telling my date a lie about myself, and she caught me. I didn’t think she’d actually demand to see the bat cave.
- Alex Reed
I know a guy who breaks up with women all the time. He calls it “going home in the morning.”
- (Unknown Author)
I miss dating The excitement of meeting someone new, that feeling of butterflies when you see if you can climb out their bathroom window...
- MF FairyPrincessSmoo @Smooheed
You can tell how single I am by the way my cat and dog wear their sombreros with quiet dignity and acceptance.
- Angie Davis @Adar79Angie
Funny Dating App Bios
Funny Dating Quotes
Group 4
The best part about speed dating is having 8-10 new guys to drink with, and none of them are keeping track of how many drinks you've had.
- Miss Moneypenny @MoneypennyNaked
My boyfriend does this cute thing where he files for a restraining order.
- Eden Dranger @Eden_Eats
Date: [looking at menu] Want to share anything?
Me: Oh. I made out with your brother once....God that feels good to get off my chest. You?
- Amanda Hugnkiss @caliluvgirl77
Guy: You’re the prettiest girl I’ve ever seen.
Girl: You just want to have sex with me.
Guy: Wow, you’re smart too, I like that.
- Your Mom @HorribleDancer
My girlfriend said I was too controlling, and it wasn't her turn to speak.
- C'est la vie @Robert_Beau
Funny Dating Quotes
Group 5
An online dating site for really old people called Carbon Dating.
- Kelkulus @kelkulus
Hi mom and dad, meet my new boyfriend, Netflix
- Swishergirl @Swishergirl24
[determined not to have any awkward silence during date]
'So, what's your favorite part of a banana?'
- Brent @murrman5
Funny Dating Application
Told a girl she's more attractive when she's not wearing glasses and she said I'm also more attractive when she's not wearing glasses.
- Kevin O'Neill @KevinBuffalo
I just cancelled a date for tonight & told the dude I was sprayed by a skunk. Who would make that up? Me. I would make that up.
- Kate @Juststopkate
Funny Dating Quotes
Group 6
Dating is where you pretend you’re someone you’re not to impress someone you don’t know.
- Melanie White
I like to date schoolteachers. If you do something wrong, they make you do it over again.
- Rodney Dangerfield
Save a boyfriend for a rainy day, and another, in case it doesn't rain.
- Mae West
Nothing defines humans better than their willingness to do irrational things in the pursuit of phenomenally unlikely payoffs. This is the principle behind lotteries, dating, and religion.
- Scott Adams
Kissing is our greatest invention. On the list of great inventions, it ranks higher than the Thermos bottle and the Airstream trailer; higher, even, than room service.
- Tom Robbins
A kiss is a lovely trick designed by nature to stop speech when words become superfluous.
- Ingrid Bergman
The main lesson I took from Lady and the Tramp is that dating below your station might result in someone who can get you free spaghetti.
- MehGyver @AndrewNadeau0
One day, some guy is gonna see me eating a whole rotisserie chicken with my bare hands in my parked car and think 'That's her, she's the one.'
- Eden Dranger @Eden_Eats
Ready for more? Go here:
Funny Dating Tweets
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