40-year-old Andy Stitzer (Emmy-nominee Steve Carell) has done quite a few things in his life. He's got a cushy job stamping invoices at an electronics superstore, a nice apartment with a proud collection of action figures and comic books, good friends, a nice attitude. But there's one little thing he hasn't quite gotten around to doing yet - something most people have done by his age. Done a lot. Andy's friends decide it's their duty to help Andy out of his dire situation and go to great lengths to lure their friend out of his lifelong chastity.