At the opening we meet Princeton, in a graduation cap and gown, who wonders what he is now going to do after graduation.
On a dilapidated street in an outer-outer borough of the city, Brian and Kate Monster both agree that life is not treating them fairly. He is unemployed; she is single. Joining in the chorus are embattled room-mates, Nicky and Rod; Brian's Japanese fianc?e, Christmas Eve; and finally Gary Coleman ? yes, that Gary Coleman ? who's the neighbourhood's superintendant. He helps new arrival Princeton get an apartment.
Nicky swears he'd stand by Rod though Rod protests he's not gay. Meanwhile, Princeton decides to find his role in life. He runs into Kate Monster, who declares that her purpose is to open a school devoted to Monsters. Princeton makes a racist statement about Monsters, and he and Kate explore the notion that everyone's a little bit racist.
At her teaching job, Kate is assigned an important lesson. She decides to teach the kids about the Internet, but neighbour Trekkie Monster upstages her by insisting that the internet is for porn!
Princeton asks Kate for a date that night. They go to a club, where Brian warms up the crowd. Chanteuse, Lucy The Slut, then sings that she can make anyone feel special. The trouble-making Bad Idea Bears get Kate and Princeton drunk and send them home, where they "get it on" noisily.
Meanwhile, a sleeping Rod dreams that Nicky is in love with him; in real life, Kate expresses her fondness for Princeton and he gives her a lucky penny.
Brian and Christmas Eve get married. At the reception, Nicky suggests that Rod is gay. Rod overhears and defensively brags about his girlfriend in Canada. He kicks Nicky out of the apartment. Princeton realises he's forgotten his purpose in life, and he breaks up with Kate, who recognises the fine line between love and a waste of time.
A few weeks later, Princeton is in a funk. In the city, Princeton hooks up with Lucy. Kate Monster sees them together and gets upset, so Christmas Eve helpfully explains the hatred that arises. Kate writes Princeton a note asking him to meet her on top of the Empire State building. Lucy reads the note and destroys it.
Meanwhile, Nicky has no place to live, and asks Gary for help. Gary explains the concept of taking pleasure in other people's pain.
Kate waits in vain for Princeton atop the Empire State Building. She throws his lucky penny off the side, and it lands in Lucy's skull 102 stories below. Princeton, Nicky, and Kate all remember a simpler time.
Meeting homeless Nicky on the street, Princeton decides to help Kate open her Monster school, and they enlist others to help raise money. Falling very short, they turn to Trekkie Monster, who saves the day. A thrilled Kate gets her school. Rod appears and comes triumphantly out of the closet. He asks Nicky to move back in, and in return Nicky brings out someone who looks just like himself: a boyfriend he found for Rod! Meanwhile Kate, touched by Princeton's generous action, agrees to try a relationship again.
A newcomer to the street makes Princeton finally realize his purpose: to put on a show about struggling through your twenties! Everyone agrees that it's a bad idea. Seeing his sadness and frustration, his friends console him, teaching him that everything in life, good and bad, is only for now.
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