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.

Ryan and Jennifer are opposites who definitely do not attract. At least that's what they always believed. When they met as twelve-year-olds, they disliked one another. When they met again as teenagers, they loathed each other. But when they meet in college, the uptight Ryan and the free-spirited Jennifer find that their differences bind them together and a rare friendship develops.