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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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  1. 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]
    • “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.
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2

Brainstorm about the zombie apocalypse.

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4

Open up the conversation with a pun or joke.

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  1. 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]
    • 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!”
7

Talk about some of your worst fashion choices.

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  1. 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]
    • 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?”
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8

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

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  1. 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]
    • 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
    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.

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Tips

  • 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]
  • 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.
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About This Article

Imad Jbara
Co-authored by:
Dating Coach
This article was co-authored by Imad Jbara and by wikiHow staff writer, Janice Tieperman. Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth. This article has been viewed 232,145 times.
29 votes - 62%
Co-authors: 10
Updated: July 4, 2024
Views: 232,145
Categories: Conversation Skills
Thanks to all authors for creating a page that has been read 232,145 times.

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