Top 36 Funny First Date Questions - Cool Dating Advice

Top 36 Funny First Date Questions

Funny first date questions

You are going on the first date with someone you met online so what do you do? You ask them some funny first date questions to break the ice. It’s not so much the question is funny it is the answer should be a good one.

My top 5 of the 36 funny first date questions are:

#1 What is your most embarrassing moment?
#2 If you were a porn star what would your stage name be?
#3 If you were a boxer or UFC fighter what would be your nickname?
#4 You won 5 million dollars what would you do?
#5 If you had 48 hours to live what would you do?

You have to look good and you need to be funny. If you can make them laugh with some fun questions that would help break the ice.


People love to laugh and getting them to laugh on a date would be a big win.

You may not be a funny person which is fine. If you can just ask some of the questions below maybe they will think you have a good sense of humor.

That could be enough to land a second date if they like you on the first date.

The questions might not be funny as it is more of the answer we want back from the date to be funny. Don’t embarrass them especially on the first date but see if you can get some laughs.

Here are the best questions to ask on a first date with someone you met online or offline.

Here are some fun questions to ask when on a date

What is a weird talent you have?

  • Weird sounds they may make
  • Talent with their tongue
  • Joint bending or double-jointed

See if they can give you two truths and a lie then see if you can figure out the lie

  • Went skydiving at 12
  • I have a tattoo on my back
  • Got my black belt in Jiujitsu

Which one is true?

What is the dumbest thing you have ever done in the name of love?

  • Bought a billboard to ask a date to the prom
  • Bought expensive gift

What is your most embarrassing moment?

  • Falling on your face in the school play
  • Losing a tooth in football practice and walking around with tooth missing

What was the funniest injury you have ever had?

  • Injuries are usually not funny but do you have anything that you were not seriously hurt

If you were a porn star what would your stage name be?

  • I think it goes the street you live on and your last name that would be your porn name

This is a really good funny first date question to ask. It should be pretty funny and you should have a ton of laughs doing this one together. You may be able to dream up other ways to come up with porn names.

If you were a pimp what would your pimp name be?

  • Come up with something stupid and fun for this like Red Velvet Daddy

Not that being a pimp is good so make sure whoever you are out on a date will not get offended by this one. Instead of being a funny first date question maybe save this one for the 3rd or 4th date.

If you were a boxer or UFC fighter what would be your nickname?

  • I fought in 2 fights one pro and one amateur. When my name was announced they called me Derek “The Dancing Machine” Carter

I know that the fights I did were not UFC but it’s easy to come up with names from boxing or the UFC. A gym close to me the owner is Matt “The Immortal” Brown who use to be an awesome UFC fighter.

You won 5 million dollars what would you do?

  • Retire on an island
  • Pay off debt
  • Buy a second house
  • Help the poor
  • The possibilities are endless
Wealthy couple on yacht

Have you ever spit in someone’s food?

  • Yes my last boyfriend or girlfriend then tell why you did it
  • This may freak out the date if you have done it before so maybe lie on this one

Have you ever went pee in a public area?

  • Most men have but maybe not all women have done it

Have you ever been arrested for indecent exposure?

  • If you have not been arrested have you ever gone streaking in public
  • Just like the movie Old School where Will Ferrell goes streaking in the quad

A plane with you on it is going down and there is only one parachute for you and your wife or girlfriend what do you do?

  • I would try to tandem jump but you better not let go

What am I thinking right now?

  • This would be fun to guess
  • There are a ton of rabbit holes this could go down

Did you have a friend set up a secret code to get out of this date if it goes badly?

  • If the date is going badly you might not want to ask this one

What do you fear the most?

  • Snakes
  • Buried alive
  • Shark attack this list can be endless
  • There are many things each of us is scared of

What Halloween costume best fits your personality?

  • This can go comic, sexy or nerdy depends on the date

If you had 48 hours to live what would you do?

  • This may get interesting
  • As much a  humanly possible
  • I would also pray for an extra 48 hours

You a nice person or a naughty person?

  • If they say naughty then ask what kind of naughty
  • They say they are nice then at least your out with a somewhat safe person

Name one food you could eat for the rest of your life?

  • People would probably pick pizza
  • Some might choose beer

If you could drink any type of alcoholic drink as much as you want without gaining weight what drink would it be?

  • Strawberry daiquiri
  • Beer makes you gain weight just ask a freshman in college

What music drives you nuts?

  • Country
  • Heavy metal
  • Rap
  • What type of music do you hate

If you do not like someone do you punch them or walk away? Why?

  • Worlds too dangerous I would walk away

This one may not be a funny first date question so again hold off to the 3rd date before asking.

If you have $5 for the Dollar store what do you buy?

  • Condoms
  • Hair gel
  • Body spray what do you need for this date
  • Candy for the date
  • Chips

Name a prank you did on a friend?

  • Pranks are fun unless someone gets hurt
  • Be real on this one

Do you have any odd piercings and if not would you ever get one? Where?

  • This may get interesting
  • If they have an odd piercing in an odd place ask if you can see it

Name a movie that sucked and why?

  • There are plenty to choose from
  • You may want to pick a type like comedy or Sci-Fi

Tell me the funniest pickup line someone said to you?

  • This will be good
  • The pick-up lines will hopefully be entertaining

Do you think you could survive a zombie apocalypse? What weapon would you bring?

  • Hell yes, ninja swords two of them
  • Guns you can run out of bullets that is why I like the sword idea

Definitely ask this one to your list of funny first date questions to ask. Unless you know they totally hate SciFi type shows.

Dating question what weapon carry zombie Apocalypse

What’s your favorite bugs bunny show?

  • The one where bugs bunny smelled ether
  • There are so many but if you are young you may not know bugs bunny

What is the last dream you remember?

  • Many people do not remember dreams so this might be a no go
  • Depends on the dream and if you do remember make sure it’s not too weird or out there

What’s the worst thing you have ever eaten?

  • You can list them all out but I hated eating liver as a kid
  • I ate worms for extra credit in biology in 9th grade, what have you eaten

Did you ever get in trouble in school? What did you do?

  • Throw spit wads
  • Get in a fight
  • Skip school
  • What did you do?

What did you want to be when you were growing up as a kid?

  • Bruce Lee because he was a badass
  • Clint Eastwood
  • Wonder Woman
  • Mother Teresa
  • There are many to choose from

After a night of heavy drinking, what food do you crave the most?

  • More alcohol
  • Breakfast
  • Tomato juice
  • McDonald’s
  • Starbucks

Have you ever been in a public restroom only to find out there is no toilet paper? What would you do?

  • Put a hand under and ask for a paper
  • Yell for help
  • Call a friend


These questions are a guideline to be used as you see how the date is going. Some you can use if it seems like they will work but be careful about which ones you pull out of your hat.

If you pull out the wrong funny first date question they may think you are a bit odd. You can see these questions will get some laughs if you have someone that you are out with that has an open mind.

Get out there and find someone to date so you can ask them all these cool questions.

You can even use these questions on a second, third, or fourth date. If you can get your partner to start laughing it will be a really awesome fun first date.

Recent Posts