Directed by Judd Apatow, starring Steve Carell, Catherine Keener, Paul Rudd, Romany Malco, Seth Roger, Leslie Mann, Jane Lynch and Elizabeth Banks.
Andy Stitzer (Carell) is almost content. Stamping invoices at an electronics store is his job. His bachelor pad displays his mammoth collection of action figures, packed in their original boxes. He's got good friends. But he has never had sex. Too many past bad experiences have dampened his interest. Now he just avoids women completely.
When Andy breaks the news to his friends and co-workers David (Rudd), Jay (Malco) and Cal (Rogen), they first presume he's gay but then set him on a sex education journey. They consider it their duty to help him out and to find him some action. They bestow their pooled wisdom on him with the best and worst techniques for picking up women which paves the way for comical opportunities.
But they mess up. They send Andy running when they hire him a prostitute who turns to be a transvestite. The winning formula seems to be to ask women lots of questions and only questions. Understand?
Then he unexpectedly falls in love with a 40-year-old mother of three who runs the 'We Sell Your Stuff on eBay' shop across from his workplace. His friends believe Trish (Keener) is enough to lure him out of his lifelong chastity, but then Andy and Trish decide on a no-sex relationship.
When things get serious and all the friends individually find love, the humour dies and token scenes of kiss and make-up are queued.
Steve Carell is perfectly cast as the sweet protagonist, his nerdiness being innately funny. But the film is carried by him, good thing for Carell but bad if you don't find him loveable and goofy. Then, it's doomed.
This is another version of 'American Pie'. The difference is maturity. 'The 40-Year-Old Virgin' tries to hit home the sweetness more so than the raunchiness, which is to the detriment of the humour. As well as lacking comedy, it lacks oomph overall. One of the best scenes is when Andy gets his chest hair waxed, or some of it at least. The pain is real as Carell did actually get it waxed. Improvisation is best!
It's good but forgettable and you may be better off revisiting the immature and hilarious 'American Pie'.