Top Funny Second Date Questions - Cool Dating Advice

Top Funny Second Date Questions

So, you’ve made it past the first date. The second date is what everyone always hopes for. Anyone who has been on several dates will tell you that the second date is never guaranteed.

The fact that you made it this far is very telling.

Sometimes the second date can be more difficult than the first.

Yes, it’s true if you’re the type who is continuously nervous all the time. You face the struggle of trying to keep it together while somehow impressing your date enough to want to continue to see you.


The best way to go about this is with a little bit of humor.

Here we’re going to give you our top funny second date questions that are sure to break the ice and keep the conversation flowing.

What’s your rule for eating food after it’s been dropped on the floor?

Everyone eats food that has been dropped on the floor. Admit it, you have, and so has everyone else.

Asking someone a funny food-related question is always an excellent way to break the ice.

It’s not a life or death question, and everyone can giggle at it. You don’t want to put your date in an odd spot by talking about politics or something like that right off the bat.

Asking a silly question about food is the best way to get things going.

What superhero is your dog or cat most like?

Do you want to make your date think? If so, this an odd question to get the ball rolling.

Most people would ask their date what superhero they would rather be like. You take things in a whole different direction by asking them what superhero their pet most closely resembles.

Your date will have to think for a minute or two to come up with the right answer.

What happens if they don’t have a pet? It looks like you’ll have to order an appetizer and ask one of the other questions on our list.

What is the worst excuse you gave to call off sick at work?

You’ll want to follow up this question by asking why did they come up with the excuse to get off from work.


The chances are that both the excuse and the reason is probably going to be hilarious.

Everyone out there has had to come up with some silly reason why they couldn’t go to work one day. You probably have a few excuses that will send your date reeling in laughter.

This is a great question if you want the conversation to go elsewhere. There are a million different directions the conversation can go, and all of them can be a total blast.

Have you ever sat next to someone who smelled bad on a bus, train, or plane? If so, what did they smell like?

You don’t need to be a world traveler to have sat next to someone who had a nasty odor.

Sometimes you can tell right away what’s causing the odor, but there are also those times when you can’t. If your date has no idea what caused the person to smell so awful, then ask them to come up with a reason why. It’ll be funny to see what they think maybe the culprit of the person’s bad odor.

Have you ever gone to the bathroom in your pants in a public place as an adult?

You’re not going to want to ask everyone this question. It’s only a question for those who you think are suited for this type of discussion.

Everyone has an accident story, but not everyone wants to share it. Don’t be surprised if they ask to move onto a different topic.

This might be one of those questions that you ask after you’ve had a drink or two under your belt. It’s a fun question for the right person if they are the type who likes to laugh at potty humor.

Who is your favorite Simpsons character?

If you know they watch another cartoon, you can choose something other than The Simpsons. The only thing that matters is that the cartoon has plenty of characters.

You could also substitute a cartoon for a sitcom or something else. Ask your date why they chose that character when your date answers. The reason why they chose the character may be very telling about their personality.

You might find out that your date is not the person you think they are after they’ve answered this question.

What’s the one smell that you hate the most?

Everyone has at least one smell they hate more than anything else. Sometimes the smell someone hates is so weird that it’s hard to believe.

This is also a great question to ask if there’s a smell that you hate that most people love.

Your date will ask you what smell you hate the most, and when you tell them it’ll spark a far-out conversation.

Sometimes the answer to the question isn’t what you’re after, what you want more than anything is to get the ball rolling and have a more in-depth conversation.

Body Odor on Date

What is the worst lie that you ever told someone?

The answer you get back from this might scare you. A question like this one can open up a can of worms that you never knew existed.

Be careful what you wish for if you end up hearing something so hideous that it makes you wish that there never was a second date, to begin with.

Lies are something everyone tells, but some people tell whoppers that most wouldn’t ever consider trying to pull off.

What song do you think would be best suited for a colonoscopy?

Here is a funny question that can really take you places. No one ever wants to have a colonoscopy.

The thought of someone putting something where the sun doesn’t shine makes most people a little squeamish.

That’s why trying to come up with a song for the procedure is so funny. This is one of those questions that makes someone think and they will overtly try to be funny.

Have you ever blamed a fart on a pet?

Farting is another one of those topics that can be hit or miss. You have to judge your date on this one.

It might be funny to ask if they’ve ever blamed a fart on a pet.

If you know they’ve never had a pet, then ask if they’ve ever farted and blamed someone else for it. Just because everyone farts don’t mean that they like to talk about it.

If your date has a good sense of humor, then they’ll probably bust a gut laughing while talking about their farting history.

What’s the dumbest thing you’ve ever done while intoxicated?

Again, this is one of those questions that you have to know your date to ask. Not everyone drinks or using intoxicants, so you’ll need to tread lightly on this topic.

If you know they’re the type who enjoys a buzz, then ask if they’ve ever done anything funny while intoxicated. Everyone who enjoys overindulging a little has at least one story where they or someone they were with did something that was funny.

What’s the one item that you’d buy at Dollar Tree right now if I gave you a buck?

Not only does this question have the potential to be funny, but it also can provide quite a bit of insight about your date.

As you probably already know, everything at Dollar Tree costs a dollar.

Dollar Tree has a surprising number of items that only cost a dollar. If you’ve never been in a Dollar Tree, then you’re missing out on one of the best shopping experiences ever.

If there are no Dollar Trees where you live, then ask the question about a store where everything is sold at a fixed price.

What food do you hate the most?

You’ll be hard-pressed to find someone who likes every food.

Follow up with asking why they hate the food. Sometimes there’s a funny story behind the reason why they hate the food. Also, sometimes, people hate the strangest of foods.

Wouldn’t it be crazy if you found out your date hated pizza?

There are so many conversation avenues that you can go down when talking about foods that you love and hate.

Ask them what’s the one part of their body they’d like to change and why.

You don’t have to be vain to not like a specific part of your body. You might wish your fingers were longer so you could play the piano better, or you had smaller eyes.

It’s not only good enough to ask the person what body part they would like to change but why as well. Sometimes the why can be hilarious and can lead you down a path of all kinds of hilarity.

How long should a person wear their underwear before changing them?

You might be surprised to learn that some people wear the same underwear for days on end.

Your date might give a surprising answer to this question. It’s not unheard of for someone to wear the same underwear for days upon days.

Hopefully, for the sake of your nose, your date changes their underwear every week, at least.

Have you ever shot milk out of your nose?

It doesn’t have to be milk. For some reason, it seems that milk is the most common liquid to be shot out of someone’s nose.

Usually, the reason for it is that someone is laughing while they take a drink of something. What they are laughing at can be quite funny since it made them giggle so hard liquid came shooting out of their nose.

Have you ever been arrested?

If they say yes, then follow it up with a question about jail or prison. If they’ve been locked up, then your date probably has some pretty interesting stories.

Jails and prisons are full of characters who are always up to something wild. You might not want to know that the person you’re falling head over heels for has been in the slammer.

Hopefully, they were put behind bars for something not too bad and not something that will cause you to have goosebumps.

Do you have any tattoos?

If you see the person has tattoos, you might ask if they have some you can’t see. You can also ask if they have anything pierced that you can’t see.

Hopefully, your date isn’t getting the impression that you’re asking to see what’s underneath their clothes.

Sometimes people do have tattoos that you can’t see for one reason or another. If a guy is wearing a long sleeve shirt, he might have tattoos being covered up by his shirt.

What is the dumbest hairstyle that you’ve ever had?

Every person at some point in their life has tried to be trendy. The attempt to fit in the crowd has no doubt led them to get a stupid haircut.

You can ask them why they got the haircut or how did it make them feel. The answer here might be a surprising window into their character.

Some people do the craziest things to their hair, and it’s especially common for teenagers to get far out haircuts.

What’s the most awkward kiss that you’ve ever experienced?

Love isn’t full of sweet-smelling flowers and smiles. Sometimes things such as kisses can be quite awkward.

Locking lips with someone might seem like an easy task until you begin thinking about how awkward of a situation it can be.

What about those kisses that the receiver never knew were coming?

If those weren’t bad enough, then there’s the possibility of someone biting you. Anyone who kisses a lot knows that there are more than enough opportunities for something weird to go down when you’re trying to get a smooch.

What’s the funniest thing you’ve ever read on a bathroom stall?

Bathroom stalls are notorious for having all kinds of funny stuff written on them. The most creative writers in the world seem to hang out in bathroom stalls. You’re bound to get an interesting answer or two from this question since everyone uses public bathrooms.

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