Starting a Weird Conversation: Funny, Creative, & Thought-Provoking Openers

The weirdest, wackiest lines to defuse an awkward situation (or intensify it)

Co-authored by Judith Gottesman, MSW and Bailey Cho

Last Updated: November 3, 2023 Fact Checked

Don’t know what to say in a tense situation? Break the ice with a weird conversation starter! Whether you want to create a memorable impression or make someone smile, asking an unconventional question is the best way to get to know someone better. If you're looking for inspiration, here's a list of 50+ weird openers guaranteed to spark an exciting conversation via text or in person.

Things You Should Know

The weirdest conversation openers involve hypothetical situations or niche pop culture references, so have fun coming up with unique questions on the spot.
Humor is a great way to break the ice , so don’t be afraid to create weird, silly questions.
To keep the conversation going , ask open-ended questions that require more than a “yes” or “no” answer.

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Weird Conversation Openers

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2

What’s your biggest irrational fear?

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3

If you had to fight any historical figure, who would it be and why?
4

Do you believe in conspiracy theories? If so, what’s your favorite one?
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6

Walk me through your ideal funeral.
7

Most attractive cartoon character?
8

Do you have any public restroom horror stories?
9

If you could only eat 3 foods for the rest of your life, what would they be?
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11

If you were born 100 years earlier, what would your occupation be?
12

Create your perfect band with 5 solo artists, dead or alive.
13

Is a hot dog a sandwich? Why or why not?
14

Rank every Shrek movie from best to worst.
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16

Do you believe in aliens? Why or why not?
17

What’s the funniest thing you believed in as a child?
18

Would you rather fight 100 zombie-sized chickens or 100 chicken-sized zombies?
19

If you could remove one state from the US, which would it be and why?
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21

What scientific experiment would you perform (if money and ethics weren’t an issue)?
22

Where’s the most inappropriate place you’ve farted?
23

Would you rather only be able to sing to communicate or dance to get from one place to another?
24

If you could be any age for one year, what age would you pick and why?
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26

Do you talk to yourself? If so, what do you talk about?
27

How long would you last in a zombie apocalypse?
28

If you could eliminate one word from existence, what would it be and why?
29

If you were invisible for a day, what would you do?
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31

If you had to lose a limb, which one would it be and why?
32

If you had to rename the color red, what would you name it?
33

Would you rather watch the same movie or listen to the same song for a year?
34

What’s the weirdest dream you’ve ever had?
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36

Would you rather detect any lie you hear or get away with any lie you tell?
37

How early do you get to the airport?
38

What’s the worst gift you’ve ever received?
39

If you could make one thing illegal, what would it be and why?
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41

What’s the strangest thing about your culture?
42

Give me 3 unpopular opinions–GO!
43

What’s the scariest movie you watched as a child?
44

What inanimate object do you want to be reincarnated as and why?
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46

Would you rather be fluent in every language or be able to communicate with animals?
47

If you were the president, which national holiday would you declare?
48

If you became famous, what would it be for?
49

Would you rather never sleep again or never eat again?
50

If you could time-travel, which year would you go to?
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Keep the conversation going by asking them follow-up questions about themselves. Don’t be afraid to get real!

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