Andy is one of those guys whose life is a workaround. What he doesn't understand, he avoids, finesses or fakes. On the job at the electronics superstore where he works, his fellow employees spend a lot of time talking about women, and he nods as if he speaks the language. Then they rope him into a poker game, the conversation turns to sex, and they look at him strangely when he observes enthusiastically how women's breasts feel like bags of sand.
The buddies are wonderfully cast. David (Paul Rudd) is still hopelessly in love with a woman who has long since outgrown any possible interest in him; Jay (Romany Malco) is a ladies' man who considers himself an irresistible seducer, and Cal (Seth Rogen) is the guy with practical guidance, such as "date drunks" and "never actually say anything to a woman; just ask questions." All these guys have problems of their own, and seem prepared to pass them on to Andy as advice; listen with particular care to the definition of "aftercourse." Also at work is Paula (Jane Lynch), Andy's boss, a tall, striking woman who is definitely not a 40-year-old virgin; after asking him if he's ever heard of just being sex buddies, she promises him, "I'm discreet, and I'll haunt your dreams."
Andy would just as soon stay home and play with his action figures. But his friends consider it a sacred mission to end his 40-year drought. In a singles bar, under their coaching, he separates a tipsy babe from the crowd; his alarm should have gone off when she asks him to blow into the breathalyzer so she can start her car. In a bookstore he asks a cute sales clerk one question after another, which works charmingly until she finds out he has no answers. He goes to one of those dating round-robins where a buzzer goes off and you switch tables, giving the movie an opportunity to assemble a little anthology of pickup cliches.
And then there's Trish (Catherine Keener). She runs a store across the mall, where you can take in your stuff and she'll sell it on eBay. Andy knows right away that he really likes her, but he's paralyzed by shyness and fear, and the way she coaxes him into asking her out is written so well it could be in a more serious movie. Or maybe it is; there's an insight and understanding under the surface of "The 40-Year-Old Virgin" that is subtle, but sincere.
On the surface, the movie assembles a collection of ethnic types as varied as "Crash." It has fun with them, but it likes them, and it's gentle fun that looks for humanity, not cheap laughs. Consider the character who unexpectedly performs a Guatemalan love song, or Andy's neighbors, who like to watch "Survivor" with him, although he has to bring the set. The movie approaches the subject of homosexuality without the usual gay-bashing, in a scene where the guys trade one-liners beginning "I know you're gay because" and their reasons show more insight than prejudice.
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