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.

Two recently laid-off men in their 40s try to make it as interns at a successful Internet company where their managers are in their 20s.