Whole New Thing (2005)

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.

A midwestern teacher questions his sexuality after a former student makes a comment about him at the Academy Awards.

An uptight insurance man and his film-censor wife become a kinky couple's landlords.

Accompanied by her closeted gay buddy, a promiscuous teenager sets out to find her long-absent father.

In the fall of 1994, a teacher at Chicago's run-down Steinmetz High conspires with the school's academic decathlon team to cheat on an academic competition.

In the wake of a freak accident, Lance suffers the worst tragedy and the greatest opportunity of his life. He is suddenly faced with the possibility of fame, fortune and popularity, if he can only live with the knowledge of how he got there.

A 16-year-old girl visits her gay half-brother and ends up seducing his boyfriend, thus wreaking havoc on all of their lives.

A teenager transitions from female to male, and his family must come to terms with that fact.

When one school teacher gets the other fired, he is challenged to an after-school fight.

When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters force him on a journey where a fortune awaits him.