A thief makes a disturbing discovery in the house where he breaks in. Later, when he returns to the same house with his partner in crime, things are no longer how he expected.
Recent MIT grad Matt Franklin should be well on his way to a successful career at a Fortune 500 company, but instead he rebels against maturity by taking a job at a video store. Matt rethinks his position when his unrequited high-school crush, Tori, walks in and invites him to an end-of-summer party. With the help of his twin sister and his best friend, Matt hatches a plan to change the course of his life.
Uptight lawyer Peter Sanderson wants to dive back into dating after his divorce and has a hard time meeting the right women. He tries online dating and lucks out when he starts chatting with a fellow lawyer. The two agree to meet in the flesh, but the woman he meets -- an escaped African-American convict named Charlene -- is not what he expected. Peter is freaked out, but Charlene tries to convinces him to take her case and prove her innocence. Along the way she wreaks havoc on his middle-class life as he gets a lesson in learning to lighten up.