Carly Zinderman
Conscientious and timely Content Provider

Feel shy and awkward? Or just fear being shy and awkward? 

You’re not alone — 40 to 45 percent of all adults consider themselves to be shy, according to Bernardo J. Carducci, Ph.D. Being an introvert can make it hard to start conversations, since there are often many things shy people tend to worry about when approaching someone new, like the potential for awkward silences, embarrassing moments, and that horror of all horrors, pointless small talk. To make things a little easier on yourself, it can be helpful to break the ice with funny conversation starters (just keep topics in the clearly "safe for work" category). 

Unless you happen to find yourself in a situation where you know a classic cornball joke will work, stick to openers that are a little more on the creative side to help work your way into a meaningful conversation. Here are a few idea topics to get you started: 

Funny Questions to Ask—That Can Elicit a Humorous Answer

People love to talk about themselves, and so asking a question is a good way to break the ice and get the other party going (which means less work for you!). Here are a few examples to get you started:

1. “What’s the most bizarre thing that you’ve ever eaten?”

Everyone’s a foodie these days — they may tell you about the first time they tried a certain type of food or followed in Andrew Zimmern’s footsteps.

2. “What makes you laugh?”

This can be a great way to gauge their sense of humor (and how far you can take things).

3. “Tell me the thing that made you laugh most this week.”

This spin on #2 is a little more specific.

4. “What was the funniest movie that you’ve ever seen?”

This is a way to find another possible talking point, as well as feel out more about their sense of humor.

5. “What is the worst advice that you’ve ever taken?”

It’s a personal question, but not too personal, and it has the potential to result in a funny anecdote — perfect icebreaker!

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

Openers like this one are especially great at networking events and can lead to an exchange of stories.

7. “What’s the worst date that you’ve ever had?”

This is a good conversation opener in a variety of situations — and nowadays especially, there are plenty of quality Tinder mishap stories to go around. It’s up to you whether this qualifies as a good conversation starter on an actual date, though.

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

This is a similar alternative to #7—and something everything has experienced.

9. “What is the magical power that you wish you had?”

Questions like this one are whimsical, childlike, and thought-provoking all at once.

10. “Know any funny conversation starters?”

Hopefully, the irony of the question won’t be lost on your potential conversation partner.

11. “What’s your favorite celebrity scandal?”

Even people that don’t follow the daily antics of celebrities will likely have something to say about this icebreaker. A similar option: “If you could be at a dinner table with any five celebrities, who would they be and why?”

12. “Did you ever have an imaginary friend?”

People love conversational topics that let them reminisce about their childhood. Hopefully, this will bring them to the past, not present.

13. "If you could trade lives with one person, who would it be?"

Most people have fantasized about having a different life, so it's a related way to open a conversation.

14. "How would you spend your winnings if you won the lottery?"

Whether the response is silly, earnest, selfish, selfless, or just plain weird, this prompt is bound to get people talking.

15. "Are there any TV shows you can quote in your sleep?"

Everyone has a favorite show, and probably one they've seen many, many times. This question can also help you establish common ground.

16. "What's the worst gift you ever received?"

Bad gifts can make for great stories later on.

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

Kids say the darnedest things.

18. "Who would play you in a movie?"

You'll learn a lot about how someone perceives herself.

19. "What book would you bring to a deserted island?"

The response may shock you.

20. "Do you have any tattoos? What are they?"

This can begin a fascinating conversation about personal decisions.

21. "What's your spirit animal?"

Dog, cat, bear, rabbit...whatever the answer is, it can tell you a lot about a person.

22. "Is there a pot of gold at the end of the rainbow?"

Yes. Yes, there is.

23. "Who's the best movie villain?"

A Bond villain? Norman Bates? Freddy Kreuger? Voldemort?

24. "Who's the best movie hero?"

Luke Skywalker or Wonderwoman?

25. "What's one thing you would tell yourself 10 years ago?"

Everyone wishes they could make small changes in the way the did something or behaved.

26. "What happens after death?"

This can get a little dark, but most people have an opinion.

27. "Who is your spirit American Girl?"

This works best for a certain age demographic, but every 90s girl has an answer.

28. "Who's your favorite Disney Princess?"

...As opposed to this one, which works for everyone.

29. "If a genie gave you three wishes, what would you wish for?"

They just can't answer "infinite wishes."

30. "What's one power you wish you had?"

From flight to invisibility, the answers are endless.

31. "What's your biggest pet peeve?"

At least now you'll know not to do it.

32. "Does anything good happen after midnight?"

This may make people think.

33. "What's the best season?"

Fall. Period.

34. "Do aliens exist?"

This question can open some serious discussions.

35. "What's your favorite word?"

It makes you think about language.

36. "What's your favorite number?"

It makes you think about math.

37. "What about our society would surprise a time traveler from the future?"

People have a lot of different opinions about how society functions—and how it misfunctions.

38. "What's your guilty pleasure?"

Late night ice cream, romance novels, anything—this humanizes your acquaintance.

39. "Which fictional character would you want to be?"

This not only reveals personality but also literary tastes.

40. "Which fictional character would you date?"

Who doesn't have a crush on a fictional character?

41. "What's a secret talent you have?"

Maybe you can fit your whole fist in your mouth.

42. "What's a funny prank you've played on someone?"

It could be good.

43. "What's one embarrassing memory you have?"

Time to relive it.

44. "What's a ridiculous WIFI name you've seen?"

Some people have pretty weird ones.

45. "Do you have a signature dance move?"

Try to get her to show it to you.

46. "If you could, would you live on another planet?"

And if so, which one?

47. "What TV show was canceled too soon?"

Unfortunately, there have been some untimely cancellations.

48. "What reality show would you appear on?"

The Bachelor or Survivor?

49. "What's a silly nickname you have or have had?"

You can't always control what people call you.

50. "What's a nickname you wish you had?"

But if you get creative, maybe you can change that!

51. "If you could have dinner with one person, dead or alive, who would it be?"

You'll find out what kind of people your acquaintance admires.

52. "Would you ever read someone else's texts?"

Is it ethical if you have a very good reason?

53. "Where would you most like to be stranded?"

Travelers might not mind it too much.

54. "Would you prefer a grand, public proposal or a private one?"

Some people love a grand gesture. Others hate them.

55. "What did you last Google?"

It could be something really strange...or pretty normal.

56. "What food do you avoid at all costs?"

You don't have to be a picky eater to avoid some foods.

57. "What's a lie you've told to get out of work?"

Come on—everyone's done it.

58. "How would you commit the perfect crime?"

This one gets the other person to think.

59. "What's a funny excuse you've given to leave a party early?"

Sometimes, it's just time to leave.

60. "How would you ensure that a video goes viral?"

Some people are natural marketers—and storytellers.

61. "Have you ever picked your nose in public?"

And would you admit it?

62. "Have you ever peed in a swimming pool?"

And would you admit it?

Rapid-Fire Funny Conversation Starters

63. "Gryffindor, Ravenclaw, Hufflepuff, or Slytherin?"

64. "Would you rather have the power of invisibility or flight?"

65. "Would you rather lose social media or television?"

66. "Chocolate or vanilla?"

67. "Organization or chaos?"

68. "Dogs or cats?"

69. "Snakes or rats?'

70. "Immortality or the ability to read other people's minds?"

71. "Would you rather live forever or be happy until you die?"

72. "Would you rather be too hot or too cold?"

73. "Books or movies?"

74. "Stinky cheese—yes or no?"

75. "Physical books or ebooks?

76. "Books or movies?"

77. "Can you follow Ikea instructions?"

78. "What's your least favorite app?"

79. "Would you rather have room for growth or be perfect as is?"

80. "Would you rather live on Antarctica or Mars, assuming both could accommodate life?"

81. "Were Ross and Rachel really on a break?"

Funny-Yet-Deep Conversation Starters

You can still be humorous while digging deep. These prompts will get the dialogue flowing while prompting your new acquaintance to think. 

82. "What's one thing you've never told your best friend—but will tell me?"

(Sometimes people are more likely to divulge their secrets to strangers than friends and family.)

83. "If you had one day left to live, how would you spend it?"

Time to delve into dreams and goals.

84. "If you could change one thing about yourself, what would it be?"

Everybody has a flaw—and chances are they know it.

85. "If you had to have an extra body part, what would it be?"

Useful or strange, it's something to consider.

86. "Did you ever do something bad and no one found out?"

If they're willing to admit it, of course.

87. "If you were to trade bodies with someone of another gender for a day, what's the first thing you would do?"

Some people think about it.

88. "Does fate exist?"

If yes, does anything we do matter?

89. "What's the meaning of life?"

Does someone know the answer? Let me know.

90. "Where do dreams come from?"

And on the same note:

91. "Where do thoughts come from?"

Makes you wonder.

92. "If a tree falls and no one hears it, does it make a sound?"

Maybe there's a "right" answer to this one...or at least a debate in there.

93. "What should your gravestone read?"

A little dark, but something about which people might have an opinion.

94. "Is there life after love?"

Hopefully, the answer is yes!

95. "What would you do in the prisoner's dilemma?"

This one can get a real debate going.

Situation-Based Funny Conversation Starters

96. Tell a funny (but brief) story.

Everybody has a funny story that serves as their go-to at parties or job interviews and first dates. Instead of waiting to slip it in later in the evening, use it as a conversation opener. Just adapt it to fit the situation — i.e., so that you’re never naked or doing something illegal in said story. And keep it short and sweet so that your conversation partner has a chance to share their favorite gem, too.

97. Make an observation.

Jerry Seinfeld became rich and famous for his observational style of humor. Follow suit and find something funny to comment on — just so long as your observation is not at someone else’s expense. It’s never good to make a first impression as a “mean girl.” Instead, start a conversation by saying something about the situation that you find yourself in, like a comment on what’s for dinner, the temperature in the room, etc.

If all else fails, ask if they’ve seen the latest viral humor video or who their favorite comedian is. Asking an open-ended question about funny people is a great way to nudge your small talk in a humorous direction.

98. Have a little fun at your own expense.

There’s nothing like a little self-deprecating humor to help put others at ease and leave those awkward silences in the dust. To start a conversation this way, look for ways to contextualize poking fun at yourself; if you attend a formal event, for instance, and are underdressed, cracking a joke about how overdressed you are works.

99. Start a round of truth or dare.

Try to keep this light if you attempt the game. For instance, you might dare someone to order a glass of milk at the bar or ask someone to reveal an embarrassing secret from childhood.

100. Start of a game of "Never Have I Ever."

Read the room. Does it seem like a fun crowd? Are people willing to poke a little fun at themselves? This game can certainly get the party going and help you get to know one another a little—or a lot—better. 

Start Talking

Humor can help take the edge off a situation, and having a few funny conversation starters at your ready is a good way to skip the lackluster small talk and get straight to an interesting conversation. Now go get talking!


Carly Zinderman is a freelance content provider specializing in lifestyle including travel, food, fashion, beauty, home decor, entertainment, health, fitness and wellness, and green living.



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