When your inner compass points you towards booty, the thing you most desire.
Nick: Damn, what was up with Rob last night? Never seen him hunt a girl so hard.
Mike: Ah dude, she is the hottest girl in school! That booty gave him Captain Jack Syndrome.
When your inner-compass points you toward that which you most desire.
Especially used when a guy is going after booty.
"Dude, there's so many good girls for him, but he's too vain."
"Well, he isn't wrong; he's just got Jack Sparrow Syndrome."
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