The 40 Year-Old Virgin (2005) is a comedy movie directed by Judd Apatow. The list below collects the movies that people who loved it enjoyed most, best known first.

★ 6.7 · 8,733 votes · Comedy, Romance
At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score" by their senior prom.
Movies like American Pie →
★ 6.6 · 8,559 votes · Romance, Comedy
Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment.
Movies like Friends with Benefits →
★ 7.2 · 3,189 votes · Drama, Romance
When Isabelle and Theo invite Matthew to stay with them, what begins as a casual friendship ripens into a sensual voyage of discovery and desire in which nothing is off limits and everything is possible.
Movies like The Dreamers →
★ 6.4 · 1,007 votes · Comedy
In 1954 Florida, a group of high school boys head to a strip club in the Everglades in an attempt to lose their collective virginity. When the club's owner and his sheriff brother swindle them out of their money and embarrass them, the boys plan revenge.
Movies like Porky's →
★ 6.4 · 1,535 votes · Comedy, Adventure, Romance
A high school senior drives cross-country with his best friends to hook up with a babe he met online.
Movies like Sex Drive →
★ 6.3 · 2,771 votes · Comedy, Romance
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.
Movies like Zack and Miri Make a Porno →
★ 6.3 · 1,015 votes · Comedy, Romance
Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.
Movies like Sleeping with Other People →
★ 6.8 · 425 votes · Comedy, Romance
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Movies like My Sassy Girl →
★ 8.4 · 378 votes · Comedy, Romance
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Movies like ¿Quieres ser mi hijo? →
★ 6.9 · 2,868 votes · Romance, Comedy
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
Movies like Set It Up →
★ 6.6 · 325 votes · Comedy, Romance
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Movies like Sex Appeal →
★ 6.6 · 601 votes · Comedy, Romance
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
Movies like Bros →