Andy (Steve Carell) is, as the title says, a 40 year old virgin. He spends the film's runtime feeling increased pressure to finally lose his virginity, especially after meeting a beautiful single mother (Catherine Keener). There's nothing awkward about their eventual sex scene, but when we flash back to see the times that Andy has attempted to have sex in the past, one scene is particularly cringe-worthy: in college, a young woman tries to suck Andy's big toe while they're fooling around, leading him to kick her in the face and give her a bloody nose. It hurts to watch.