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50 Funny Conversation Starters to Keep You Laughing & Talking for Hours

You don’t have to be a social butterfly to make a good first impression. These 50 funny conversation starters will easily win someone over.

Funny Conversation Starters

Are you looking for funny conversation starters to strike up a chat? Maybe you have a crush on someone and don’t know how to approach them. Or you’re invited to an important party, but the thought of talking to strangers gives you hives. Are you on a dating app and unsure how to message someone first?

Whatever your reason for being nervous, don’t worry. Talking to people doesn’t have to be scary, especially if you use a few funny conversation starters anyone can connect with. But first, you must know the reason why you’re uncomfortable with starting conversations.

Why you’re uncomfortable starting conversations

There are plenty of reasons for this, and here are some common ones:

1. You’re shy

Not all introverts are shy, and not all extroverts are bold. But if you are a shy person, you might feel much more comfortable in your own social bubble, rather than venturing out and talking to new people.

[Read: Do guys like shy girls? 32 reasons & things that make you attractive]

2. You have anxiety

A lot of people are struggling with anxiety disorders. They find it hard to simply order a drink in a crowded cafe, so even when they have all these funny conversation starters in their head, saying them might be a challenge.

[Read: How to help someone with anxiety & not say or do the wrong things]

3. Other mental health issues

Other mental health issues could be contributing factors as well. You shouldn’t feel ashamed or let anyone invalidate your struggles.

[Read: Why we need to breakdown the stigma of mental illness]

4. It’s a learned behavior

Maybe you’re not shy, but your parents were. If you never witnessed them starting conversations with strangers, then you subconsciously learned that it’s something you shouldn’t *or can’t* do.

5. Fear of rejection

You might have tried using funny conversation starters in the past, but you have gotten rejected in one way or another. Even if you don’t remember, it could still be affecting your behaviors today. [Read: How to get someone to like you immediately]

6. You wouldn’t feel comfortable if someone approached you

Maybe you find it awkward when someone approaches you in public, so you just assume that other people would feel that way if you came up to them.

7. You’re afraid you might say the wrong things

Perhaps you’re just not very good with words. Every time you get nervous, you say all the wrong things. It happens to the best of us, so don’t be too worried.

[Read: How to get over dating anxiety: Face your fear & get back out there]

8. You think guys should message first

Most women expect the guys to be the first to start the conversation, especially on dating apps. Could that be the reason you’re getting so many matches yet barely any meaningful conversations?

[Read: 17 new dating app terms & their meanings for easy online dating]

9. You think it makes you less desirable

You probably think that you messaging first may make you seem less desirable. But you cannot be more wrong. Everyone loves a confident person. And no one seems more confident than someone who’s mastered funny conversation starters.

50 funny conversation starters that can help you out

Now that you’ve identified the reason why you’re uncomfortable with starting a conversation, it’s time for you to do something about it.

Whatever your reason is, you’re not stuck. With a little practice, you’ll be just fine. So, here are 50 funny conversation starters to give you a nudge. Because let’s be honest, who doesn’t love humor?

[Read: 41 casual conversation starters to use with a guy to get him talking]

1. Do you believe in love at first sight?

This is one of those funny conversation starters that will never go out of style. It doesn’t even have to be a pickup line—just a general question.

2. Would you cut off your little toe for $1,000,000?

This is a bizarre question that most people have never even thought about. But it’s a good, deep, and funny conversation starter. [Read: Drawing a blank? Try these easy 25 conversation starters]

3. What present would you buy me if you won the lottery tomorrow?

Of course, this is funny if you just met the person because they probably wouldn’t buy you a present!

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

This is another weird question, but you can have fun with it. It might also give you some insight into the person’s personality.

5. If you worked at a circus, which job would you want to have?

Everyone loves the circus! This will test their sense of humor and light-heartedness. [Read: How to start a conversation with a crush and woo them]

6. Tell me something funny that happened to you this week

This will get them laughing and reflecting on the good things in their life.

7. What is the worst first date you have ever been on?

We all have hilarious stories of bad dates! This is one of the greatest funny conversation starters, and you’ll learn some of the things this person considers red flags.

[Read: 40 rules & dating advice for women tired of bad dates & shitty men]

8. What is your most embarrassing moment?

Some people may not want to talk about it, but it sure is funny when they do.

9. Have you ever stalked someone on social media?

No one really wants to admit this one, but this is one of those funny conversation starters that may give you a lot of tea. [Read: How to stalk on social media & find just what you’re looking for]

10. Are you a selfie queen/king, and why?

You might get two extremes with this question. YES or NO!

11. If you could have one magical power, what would it be?

It can be anything from predicting the future to having the ability to fly. With all those Marvel movies in the theater right now, there’s no way they don’t have an answer to this.

12. What would you do if you weren’t doing your current job?

Everyone has a dream job, which may not be their current one. Get them to talk about their hopes and dreams in a lighthearted way.

13. What’s the worst advice you’ve gotten but actually followed?

We’ve all followed some bad advice, and it usually leads to some pretty funny stories. [Read: How to keep a conversation going with the opposite sex]

14. Do you know any funny conversation starters?

Hahahaha. Get it? [Read: 15 easy conversation starters you can use with a guy you like]

15. What is the last really dumb thing that you did?

We all do dumb things. This question will bond you guys as you share your silliest moments.

16. What are the 3 craziest things on your bucket list?

Everyone should have a bucket list. It’s always fun to know about all the wild things someone wants to do before their life comes to an end. [Read: Sexual bucket list: 35 dirty deeds to build your naughty wishlist]

17. What do you think you were in a past life? *Or do you believe in past lives?*

Stay away from religion and just have fun with this one. [Read: 41 conversation starters for couples who are just starting to get serious]

18. What’s your favorite celebrity drama?

The Kanye/Kim/Pete love triangle? Johnny Depp versus Amber Heard trial? The celebrities will give you plenty to talk about.

19. Do you think Jack could have really fit on the headboard at the end of the movie, Titanic?

It’s 2022. WHO hasn’t seen or known what happens in Titanic???

20. What’s your favourite meme?

Everyone loves memes. If someone doesn’t, it may be a red flag. [Read: How to keep a conversation going with a guy: 20 ways to connect 24/7]

21. If you could get a free pass for a day to do anything legal or illegal, what would you do?

Rob a bank? Sneak into an amusement park without paying? Spend a night in a museum? Walk around the city naked?

22. What was the most recent lie you told?

A funny response could be “my height” if you have your height on your dating app profile. [Read: The socially awkward person’s complete guide to flirting]

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

We’ve all done it, calling into work or staying home from school.

24. What’s the funniest joke you have ever heard?

You can make this one of your funny conversation starters. Everyone loves a good joke! [Read: 77 funny things to text a girl and make her laugh & love you over text]

25. If you were immortal for a day, what would you do?

Jump off a cliff? Skydive?

26. If you could meet anyone, dead or alive, fictional or real, who would it be?

They could give a heartfelt answer like their parent who passed away, or they’ll say Draco Malfoy. You’ll learn more about them either way.

27. What’s the biggest change you would like to make to your life?

A career change? Moving out of the country? Quitting their corporate job to become an artist?

28. If you had a voodoo doll and could hurt anyone in the world, would you do it?

A politician? Their annoying neighbour? Their ex? [Read: How to be funny and make people love your company]

29. If you had to pick one popular reality show to be on, which would it be?

Would they be on Too Hot To Handle or Love is Blind?

30. Would you skydive willingly?

This tells you how adventurous they are and if they like adrenaline rushes.

31. Would you bungee jump willingly?


32. What makes you unique?

If they say “nothing”, they’re telling the truth. Don’t bother with them. [Read: How to keep a conversation going with a girl you really like]

33. What kind of weird quirks do you have?

Do they hate sharing their food? Are they a clean freak? Are they the absolute opposite of a clean freak?

34. What’s your biggest pet peeve?

People who are late? Slow walkers at the train station? People not using correct grammar when they text?

35. What’s the funniest movie you’ve ever seen?

A funny response would be a movie that’s supposed to be serious but you find hilariously awful.

36. What’s your favorite song to dance to?

Are you into Tiktok songs or more unpopular ones? [Read: 15 guaranteed ways to get your crush to like you back]

37. What’s your favourite TikTok sound?

Those who vowed they would never go on TikTok are being sent TikToks, or watching reposted TikToks as Instagram reels and Facebook videos.

38. If reincarnation exists, what would you like to come back as?

A billionaire? A supermodel? The Queen of England?

39. What is one thing you can’t live without?

A person? Money? Coffee? This will tell you a lot about them.

40. If you were stranded on a desert island, what are three things you would bring?

This is one of those funny conversation starters that would make them think.

41. I bet you can’t make me laugh!

Challenge accepted! [Read: Witty banter: What it is & 15 secrets to talk witty & make people laugh]

42. Have you ever had an imaginary friend?

If they have, hopefully it was as a child *and not currently*! [Read: 20 signs of attraction in the first conversation]

43. If you had to fight an animal, what animals do you think you could take and why?

The way they approach this question would say a lot about them. Would they seriously consider their strengths and skills to fight, or do they just say something random and funny like “snakes, because they have no hands”?

44. Would you rather have eyelashes for fingers or fingers for eyelashes?

And ask them to give a reason for their choice!

45. Do you believe in ghosts?

Everyone has an opinion on this. And if their answer is yes, you’ll get to hear an interesting *hopefully not too weird and creepy* ghost story.

46. If you were a color, what color would you be, and why?

This question would tell you a lot about their personality. If they say red, they think that they’re sexy, bold, and confident. Black, they’re mysterious, secretive, and classy. White, they believe they are soft, elegant, and innocent.

This is your chance to discover if they really are the color they say they are. [Read: Feisty girl: 35 personality traits that make her so scarily sexy!]

47. What is your most controversial opinion?

This question could be one of those funny conversation starters, or the best way to detect an early red flag. If their most controversial opinion is “feminism is doing more harm than good”, yeah, run.

48. What do you think about *insert your most controversial opinion*?

Well, why don’t you say yours to see if they would think it’s a red flag or agree with you?

[Read: 31 classy, cool ways to make a guy go crazy over you & crave for you]

49. Pickup lines

Some are a little bit cheesy. Some never get old. If you know how to use them, it’ll be an easy win. [Read: How to flirt with girls: 25 secrets & 41 lines to seduce & make her blush]

50. Send a GIF

If you’re talking online, GIFs are some of the most underrated yet funniest conversation starters. Send a gif related to the information on the person’s dating profile. Sometimes, a funny “hello” GIF will suffice.

[Read: 48 Tinder conversation starters & secrets to get them itching to respond]

Everyone loves humor. So even if you’re uncomfortable being the first to talk, you still can’t go wrong with these funny conversation starters. Keep these memorized and try one the next time you want to make a good impression on someone!

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Carol Morgan LP
Dr. Carol Morgan
Dr. Carol Morgan has a Ph.D. in communication and is a professor at Wright State University where she loves corrupting young minds. As a relationship and succes...