A shipoopy is a group of four people generally consisting of an ass, a clingy douche, a nice guy and a cool chick. Usually, the ass, the douche and the chick ditch the nice guy and laugh at him. Sometimes the nice guy and the chick ditch the others but its a little awkward for the nice guy because he has little experience with women despite his obvious disposition to be nice and caring.
Wow, that shipoopy needs to split into a boy band of two and a friendly guy/girl combo.
"Shipoopi" is the title of a song from The Music Man, a Broadway musical written by Meredith Willson.
"Shipoopi" is also a portmanteau of the words "shit" and "poopie"; which is perhaps why children enjoy performing the "Shipoopi" song in Willson's musical.
lyrics from "Shipoopi":
Now a woman who'll kiss on a very 1st date,
Is usually a hussy,
And a woman who'll kiss on the second time out,
Is anything but fussy,
But a woman who'll wait 'till the 3rd time around,
Head in the clouds, feet on the ground,
She's the girl he's glad he's found,
She's his Shipoopi.