Let’s face it—starting a conversation with a guy you’ve just met or don’t know very well can seem really intimidating. You want to have a fun and engaging conversation that keeps a guy interested and avoids any awkwardness. So where do you start? Fortunately, there are so many different conversation starters for you to choose from. Here’s a list of the best talking points for a meaningful conversation with a guy that’ll leave you feeling confident and ready to start chatting!

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Funny Stories

  1. Nothing breaks the ice like a hilarious or embarrassing story. Laughter can be a great way to connect with people and relieve tension. Try telling him a joke or sharing a funny story. If he doesn’t find it funny, don’t be discouraged.[2] Keep the conversation going by asking him what he does find funny. You could ask:
    • What’s the funniest thing that’s ever happened to you?
    • What’s your favorite joke?
    • Do you have a favorite comedian?
    • What are some videos or memes that make you laugh?
    • What is the funniest text you’ve ever gotten or sent?
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Love and Relationships

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Social Media

  1. Most people spend a good amount of time online. Even if you don't have a heavy social media presence, we all have that one social media platform that we can’t get enough of or just spend too much time on. You may have even met or built a relationship with the guy you’re talking to online.[8] Here are some questions to get the conversation started:
    • What is your favorite or most visited social media site?
    • Do you spend a lot of time on social media?
    • Have you seen this meme or funny video?
    • What is your least favorite social media platform?
    • Do you prefer online or real life interactions?

Warnings

  • Avoid asking too many questions at once. The last thing you want in a conversation is to feel like you’re in the hot seat or being interrogated.[12]
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About This Article

Maria Avgitidis
Co-authored by:
Matchmaker & Dating Expert
This article was co-authored by Maria Avgitidis and by wikiHow staff writer, Donna Sarkar. Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist. This article has been viewed 45,181 times.
18 votes - 83%
Co-authors: 4
Updated: August 16, 2022
Views: 45,181
Categories: Social Interactions
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