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This phrase is commonly used to imply that you don't really care. Mostly used after lengthy discussions, and boring topics.
Girl 1: I was eating a burrito, and suddenly i forgot my guacamole! So i rushed to the store, but they were all out. All they had were fajitas, so i grabbed one of those and headed back. Can you believe that?
Girl 2: cool story, bro. Now go make me a sandwich.
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This meme is used to make fun of peoples BS storys.
Dragons are not real therefore the cool story bro adds up with the dragon part.
DougieWouggie - I lost my virginity to Megan Fox and then she sucked me off while I was asleep.
Stephon - Cool story bro, tell me the part about the dragon again.
This meme grew from the site "gamekiller.net".
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a sarcastic way to get some one to understand their own stupidity in what they just said
"SOoo i went shopping with my mom yesterday.......etc"
"cool story bro, now what chapter do you shut the fuck up?"
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Not listening and doesn't care if comes off rude
Friend: Yea so yesterday i went on this really awesome travel and it was so cool
Bored Person : Cool story Bro