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39 Funny Conversation Starters - The Only List You Need Is Here

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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Having funny conversation starters is a great way to connect with someone. It helps you make a good first impression, especially if you're crushing on someone. You need to make sure that that person will be curious about you and will try to get to know you more.

So how can you make sure you catch someone's attention in as little time as possible? By being funny, of course!

Why does being funny matter in conversation starters?

That's because when you're funny, the other person laughs and genuinely gets curious about you. It shows that you have character and that you're an interesting person.

So how exactly can you be funny when you don't have a clue who the other person is? That's what this list of funny questions is for – to help you out when you're trying to connect with someone for the first time.

Take a look below to get some ideas on the best funny conversation starters to ask that cute guy you're crushing on.

Contents

10 Best funny conversation starters

Breaking the ice can be pretty scary, especially if it's with a cute guy at a party. You need to say something cool yet make a lasting impression.

Here are the 10 best funny conversation starters:

1. What was the funniest movie that you’ve ever seen?

Is it The Naked Gun or Zoolander?

2. What makes you laugh?

Find out if he's someone you can easily amuse or not.

3. What's a funny thing you believed when you were younger?

There's no harm in talking about his childhood, as long as it was a positive experience for him.

4. What’s the most ridiculous fact you’ve ever heard of?

You can share this ridiculously funny fact too: It's impossible to hum while you're pinching your nose. Go ahead and try this one while you're at it!

5. When was the last time you faked being sick?

Was he one of those kids who faked being sick to miss school?

6. What is the funniest/craziest thing you've ever done?

Have you ever gone skinny dipping in a cold lake? That's pretty scary and funny!

7. What is the craziest bet you've ever made?

You can also answer that your friends did a bet that you should say hi to him.

8. What are things that you should not say at your own wedding?

Like, "I just came here for the cake."

9. Where would you go on vacation if you had no budget?

This is actually a pretty interesting question since you can use his answer to surprise him later on.

10. If you could host a talk show, who would you have on first?

You can get an idea of the people he looks up to and what sort of things he's interested in.

9 Funny random conversation starters

Being equipped with random conversation starters can be a big help. When you have these questions ready at hand, you'll be able to strike up a conversation with anyone right away.

Of course, these questions need to be really funny and interesting for people. If you strike it off, you'll be making a pretty good impression of yourself to others.

Here are 9 funny random conversation starters:

11. What is the strangest question you’ve been asked in a job interview?

This question will make him thoroughly think of his answer. You can use that time to come up with your own answer.

12. What’s the worst pick-up line you’ve ever been told?

Hey, no judging! Guys get told pick-up lines too.

13. What set of items could you buy that would make the cashier the most uncomfortable?

Now this is a very random question that you can ask. It will make him really think about his answer carefully since he'll want to impress you too.

14. What is the most embarrassing thing you have ever worn?

Be prepared to laugh at his answer. And be prepared to share your own embarrassing OOTD too.

15. What would be the worst “buy one get one free” sale of all time?

A pair of socks... only the free item is missing its pair.

16. If life were a video game, what would some of the cheat codes be?

If real life were like SIMS, you only need to type 'rosebud' or 'kaching' so you can get 1,000 simoleons!

17. If you could replace all of the grass in the world with something else, what would it be?

See, it's a totally random and funny question that can leave an impression behind.

18. If you had to choose one animal to help you win a fight, which animal would you choose?

Would you pick a grizzly bear or a lion?

19. What’s the best Wi-Fi name you’ve seen?

While you're at it, you might want to share some funny Wi-Fi passwords too!

10 funny text conversation starters

Even when you're communicating via text, you still need to be able to make a good impression. Thankfully, you have these funny text conversation starters that can help you out.

Here are 10 funny text conversation starters:

20. If you were a vegetable, what would you be and why?

This is a particularly good topic if he likes eating vegetables. Before asking this, you can ask if he likes to eat veggies.

21. What is your apocalypse plan?

You've got to clarify whether it's a zombie apocalypse, the Armageddon, or a pandemic.

22. What inanimate object do you wish you could eliminate from existence?

You can also ask why that is his answer.

23. If you were arrested with no explanation, what would your friends and family assume you had done?

This is a pretty interesting question to ask someone. You can see whether or not he is game for doing something crazy.

24. What is the silliest way that you’ve been injured?

This is a great way you can ask about his childhood, especially if the injury was obtained during that time.

25. What was the funniest thing you’ve seen recently online?

You can share a link to a video or a GIF of something that made you laugh too. This way, you can keep the conversation going.

26. What is a funny excuse that you have given to leave a party early?

Now this is fun! You can actually use each other's excuse if you find yourselves at a boring party.

27. What about your teenage self embarrasses you the most?

Be careful not to share something totally intimate unless you're willing to talk about it.

28. What quote or saying do people often say, but you believe is complete trash?

"Always remember that you are absolutely unique. Just like everyone else." - Margaret Mead. What quote would he share?

29. What did you think was cool as a kid, but isn’t actually cool now?

His answer to this question will give you little bits of information about his personality that you can help you understand who he really is.

10 Funny and interesting conversation starters

These are just some of our favorite conversation starters that you can ask just about anyone. It doesn't matter if you're trying to impress a guy you like or just breaking the ice with someone you just met.

You can ask these interesting conversation starters so that things don't get awkward between you two.

Here are 10 interesting conversation starters:

30. Who would play you in a movie?

Let him explain why he thinks this certain actor would play a great job in portraying him in a movie.

31. What is the weirdest thing you have seen in someone else’s home?

As long as it doesn't have anything to do with a crime, that's probably okay to talk about.

32. What is your most embarrassing moment from high school?

Prepare to hear something crazy. After all, high school was an interesting time in everyone's lives.

33. If animals could talk, which would be the smartest?

This could be a great start for a friendly debate. You can also share which animal you think would be the smartest.

34. What's the worst thing you said on a date?

You can also share some of the worst things a date has told you, like an excuse to leave the date abruptly.

35. When was the last time you laughed so hard you cried?

This will let you know the things that he enjoys and thinks are funny.

36. What’s the weirdest thing you loved as a child?

Share your own story too. You'll both laugh about these things once you reveal these secrets.

37. What’s the worst trend you’ve ever taken part in?

It's crazy that there are so many different trends being released almost every single day. You can share some of the ones that you think are the worst and some that are worth partaking in.

38. What part of a kid’s movie completely scarred you?

You can also share which kid's movie you enjoyed the most and that you can watch over and over again.

39. What’s the weirdest thing a guest has done at your house?

This will definitely be a great way to get to know the other person since you know what he considers funny.

How To Pick Funny Conversation Starters

Having a great conversation with anyone matters. This is why people try to do their best to make sure the conversation starters they have are really something of value. But how do you know if a question will work?

Here’s how to pick a good conversation starter:

1. Don't Get Too Personal 

If you've only met the person, you have to make sure that you do not ask a question that could potentially offend him. This is why you should stick to questions that are general or are okay to ask someone whom you just met. If you're unsure of a question, it may be best to avoid it.

2. Get The Conversation Going

The secret to hitting it off is to get the conversation going between you two. When you ask him something, be sure to engage yourself in conversation and keep asking him questions that matter. This will make him see that you're interested and that you're an easygoing person to talk to. Soon, he might ask you out on a date so you can keep the conversation going.

3. Get Comfortable With Your Questions

When you are trying to start a conversation with a guy you like, it's important that you are comfortable with the question you are asking. This is particularly true if the question will likely get thrown back at you and that you will need to answer it. With that in mind, don't ask questions that you yourself are not comfortable answering with someone you just met.

Downloadable and Printable List of Funny Conversation Starters

Here is a downloadable and printable jpg/pdf list of funny conversation starters (right click the image and select Save Image As...):

More Awesome Questions and Conversation Starters

By now, you probably already have a number of funny conversation topics to ask a guy that you're crushing on. But if you would like to get more ideas, here are some other questions you can ask:

  1. We also have a great selection of funny questions to ask a guy that can help you make a good impression on him.
  2. You can also ask these fun conversation starters as a way of introducing yourself and getting him to talk more about himself.
  3. Finally, here are some great questions to get to know someone so you don't get stuck in awkward silences when you're together.

In Conclusion

Now that you have these funny questions to ask, you can use them to help you start a conversation with a guy you like.

You'll find that these conversation starters are a great way to know more about the other individual. It's always great to have humor when you're trying to get to know someone. Don't be afraid to use any of these funny conversation starters and change them up a bit! Go crazy with these questions!

About The Author

Anonymous

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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