25 Questions That Can Make You Laugh Until You Cry

Guest Communication, Things to do

A huge concern for people who are in a long distance relationship is running out of things to talk about!

Sometimes it feels as if you’ve already shared every small detail about your lives or your day, and the well of conversation is running dry. You can be sitting on the phone or on video chat, aching to be with them, but feeling like you haven’t got much to say.

We’re here to help! In those moments asking your partner some goofy, funny questions can add some laughter and happy memories to the mix and banish the long distance silence.

These questions are also great for bringing up with someone that you just met online. Being playful and light can help the person you’re just getting to know feel comfortable and relaxed, and quickly open up the communication lines between you.

So don’t try too hard to be funny, or you’ll just come off as corny. But asking questions that have the potential to make someone laugh or remember something they haven’t thought of in ages, can really help you get to know someone better quickly.  

Here are some of our favorite questions that can make you laugh until you cry. The questions themselves might not all sound funny, but they are perfect for firing up a conversation, breaking the proverbial ice, sparking fun and keeping the banter flowing.


1. What’s the funniest joke you ever heard?

Whether it’s the cheesy knock-knock jokes, amusing one-liners or something wittier, jokes can be an excellent place to start and bring on some serious laughs.

2. What’s the easiest thing that you often manage to screw up?

The answer can be anything from a funny story related to forgetting a handkerchief before heading to an important meeting to screwing up boiling milk, where you look aside for a minute and it overflows.

3. What is the outright useless talent or skill that you have?

Everyone has at least one useless skill. It could be being great at flipping pens, towel whipping, or making your eyes vibrate.

4. Would you still have a job if your internal monologues at work were audible?

Internal monologue and that voice that is in your head are typically free to think or say the most outrageous things, most of which would get you in trouble in the workplace if it was suddenly audible.

5. What funny things would be on your life’s gag reel?

Share those hilarious moments in your life where anyone watching your experiences as a film would likely burst out laughing.

6. What’s the wildest or craziest thing you’ve done?

This question will always bring about an excellent story. You can share a humorous story first to set the stage before asking your partner this question.

7. What’s the one thing that you refuse to share with another person?

While some people don’t mind sharing certain items, like soap or nail clippers, some things are entirely off limits, including loofas, razors, or toothbrushes.

8. Which part of the body wouldn’t you mind losing?

There could be a few parts that you wouldn’t mind parting with. But even if you’re quite attached to it all, what part would you sacrifice if you had to make a choice?

9. What’s the funniest way that you’ve hurt yourself?

Some injuries usually come about because of being slow-witted. Share your cringe-worthy story, and it will likely leave your partner in stitches.

10. What’s the most absurd thing that you were ever tricked into believing or doing?

Asking about their most gullible moment and enjoy.

11. What common saying or quote doesn’t make any sense or ring true to you?

Money cannot buy happiness is one example of a controversial quote. Share others and laugh about the cliché quotes.

12. What’s your most embarrassing moment?

Explain a funny and embarrassing situation that you once encountered and what you learned.

13. Have you ever screwed up and escaped responsibility because nobody found out what you did?

It could be a recent mess or a sneaky experience from your younger days. This question can invites vulnerability but also allows you to reminisce safely about the more distant past.

14. What situation did movies or television make you imagine would happen every day in your real life?

Sometimes pop culture and TV can give you irrational fear of specific stuff like quicksand and memory loss (or speaking from personal experience here, piranhas).

15. What fascinating thing have you seen or read this month?

You can share hilarious clips or stories that came across online.

16. What’s the most outrageous thing that you’ve seen a teacher do?

Our teachers sometimes does some very weird things in our presence that can be pretty annoying.

17. What’s the funniest commercial you’ve watched recently, and why is it so amusing?

Many commercials nowadays are an art form. The funniest commercials or informercials function as mini-stories and can be truly hilarious and memorable.

18. What’s a cooking story where things didn’t go as planned?

Cooking is a fun activity for many people but sometimes things don’t usually go as planned. Share your funniest or most absurdly ambitious cooking fails.

19. What’s the craziest purchase you ever made?

Somethings we tend make buy things that don’t make any sense and that we regret or question later. Have you ever done this?

Other interesting questions that can make you laugh:

20.  What is the most amusing goal you had as a child for what you’d become as an adult?

21.  What hilarious superpower would you want if you were a superhero for a day?

22.  What is your favorite funny quote?

23.  What’s the best prank you’ve ever played on someone?

24.  What’s the funniest name you’ve ever heard?

25.  If you could switch genders for a week, what would you do?

Author Byline
John Simon is an experienced copywriter and relationship consultant. When he’s not working on helping long-distance couples maintain their spark, you can find him playing music in his band, traveling or having fun with his Rottweiler. He’s the Senior Editor at Sociotelligence – a site that help folks become more social.

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