How to Start a Funny Chat with a Girl

Co-authored by Imad Jbara and Janice Tieperman

Last Updated: May 9, 2025 Fact Checked

When you message a girl for the first time, you definitely want to make a good first impression. However, standard messages like “hey” or “how are you?” won’t set you apart from the crowd. Not to worry; whether you’re texting or chatting in person, there are tons of funny, clever ways to get a conversation going. We’ve put together some fun quips, questions, and other conversation starters for you to choose from before you dive into your chat.

1

Ask an outlandish “would you rather?” question.

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A silly question can make her smile and keep the conversation going. Start the chat with a funny but tricky “would you rather?” question that really gets her thinking. Then, see where the conversation goes from there!^{[1]
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- “Would you rather live in a crappy apartment with your best friend or stay in a mansion with your worst enemy” could lead to an interesting, humorous conversation.
- “Would you rather have just 1 eye or 2 noses?” or “Would you rather snack on a raw potato or an entire lemon?” could also be funny conversation starters.

2

Brainstorm about the zombie apocalypse.

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This unlikely scenario is sure to bring on the laughs. Ask about her escape plans and survival strategies if the world ever gets taken over by zombies. Then, share your survival plan with her. You’ll both share a lot of laughs as you point out the obvious flaws and issues with each others’ strategies.^{[2]
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- You might say, “Imagine that the zombie apocalypse started tomorrow. How are you going to make it out?”
- “On a scale of 1 to 10, how screwed are you if the zombie apocalypse starts?” is another great question you could ask.

3

Offer a silly but thought-provoking question about food.

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Silly, food-related questions are a funny but effective way to break the ice. You could ask one of the classics, like “Is cereal a soup?” and see where the conversation goes. These funny, harmless questions could lead to an interesting conversation!^{[3]
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- “Is a hot dog a sandwich?” or “What are your thoughts about pineapple on pizza?” are some other great questions you could ask.

4

Open up the conversation with a pun or joke.

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Puns and jokes are an iconic, memorable way to stand out from the crowd. Sprinkle a pun or joke into your first message, and see how she responds. If she finds you punny enough, keep up the wordplay in your next few messages. Who knows—she might even join in on the fun!^{[4]
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- You might say, “My roommate told me he was headed to a costume party dressed like an island. I said, ‘Don’t be Sicily!’”
- You could crack a cheesy joke, like: “How do you get a bear to climb out of a tree? Camembert!”

5

Impress her with a silly poem.

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Amp up the humor with a rhyming message. You don’t have to write out a sonnet or limerick to get her smiling. Send 1 or 2 rhyming lines, which get your message across without being too over-the-top. Then, add a little note about how “great” your poem is.^{[5]
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- You might say, “I’m glad we are a match. You are a great catch!”
- You could also send “I’m a poet and I don’t even know it.”

6

Reminisce about funny, embarrassing moments.

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Silly memories are a fun, memorable way to break the ice. Everyone has an embarrassing, hilarious story from their past. Share a tale of your own, and then ask her for a goofy, embarrassing story. Swapping stories is a sure-fire way to bring on the laughs!^{[6]
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- You could ask, “What’s the craziest thing you did over spring break?” or “Do you have any funny stories from middle school?”

7

Talk about some of your worst fashion choices.

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Recollect some of the cringe-worthy outfits you’ve worn in the past. Ask her about any infamous outfits she might’ve worn when she was younger, and share a silly tale of your own. Comparing bad fashion choices is a silly but effective way to break the ice.^{[7]
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- You might say, “I used to wear all black to school when I was in eighth grade. What’s the worst outfit you ever wore to school?”
- You could also say, “I dug up some of my old school pictures yesterday and couldn’t stop cringing. Do you have any memorable school photos?”

8

Ask her about the craziest public WiFi network she’s ever seen.

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This random but silly question can get your conversation rolling. Chances are, she’s probably seen a weird WiFi network pop up on her phone or computer. Compare notes on your best, zaniest WiFi discoveries, and see where the conversation leads to.^{[8]
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- You could say, “I was at the library today and found a WiFi network called ‘Too Fly for a WiFi.’ What’s the craziest WiFi network you’ve ever spotted?”
Leil Lowndes, Bestselling Author on Interpersonal Relationships

When starting a conversation, lead with light humor and positivity—like an amusing story or observational joke to break the ice. Avoid cynical, offensive humor. Once she's smiling, pivot to thoughtful questions allowing her vibrant personality to shine through. Balance wit and authentic interest for memorable chats.

9

Envision traditional movies as musicals.

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Ask her which movies would be better if they were recreated as musicals. Wait and see what suggestions she gives, or offer a silly suggestion of your own. Reimagining classic movies as musicals is sure to make her smile.^{[9]
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- You could joke and say, “I think Terminator would be way better as a musical. Which movie do you think would be better as a musical?”

10

Chat about a funny quarantine experience.

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Everyone has a tale from their COVID-19 quarantine. Ask about the weirdest thing she bought during the quarantine, and if she picked up a new hobby during that time. You might also reminisce on any silly Zoom call moments or funny tech problems that you ran into.^{[10]
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- You might ask, “What’s the most embarrassing Zoom call you were a part of?” or “What’s the most ridiculous online purchase you made during quarantine?”

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How can I be more entertaining?

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Stimulate the other person's interest and curiosity in your topic by considering their interests.

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Small talk isn’t very memorable in a conversation, and won’t get you too far. Instead of asking questions like “how are you” or “what’s your favorite subject in school,” play around with funny and creative conversation starters.^{[11]
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Use texting to set up dates so you can get to know each other better in person. Trying to get to know each other over text can lead to miscommunication because delivery and tone are hard to decipher over text.^{[12]
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Imad Jbara
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