The 40 Year Old Virgin

Movies Like

The 40 Year Old Virgin (2005)

Comedy, Romance

If you loved The 40 Year Old Virgin, you'll love these similar films. Handpicked based on shared themes, genre, and feel.

Another Gay Movie

Another Gay Movie

2006 ★ 6.0

Andy is your typical All-American eighteen-year-old gay virgin. Like everyone else, he's dying to have sex. Totally out of the closet and mad-crazy horny, this naïve high school senior is caught in that awkward vortex between child and adult. Much to the dismay of his mom (who wonders why all her carrots and cucumbers keep disappearing), Andy spends much of his private time practicing for the big moment when he'll finally take the plunge.

The Last American Virgin

The Last American Virgin

1982 ★ 6.6

The friendship of a group of young friends struggling with teen sex, drugs, and work is jeopardized by a romantic interest which may turn pals into bitter rivals.

American Pie

American Pie

1999 ★ 6.6

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.

Splendor

Splendor

1999 ★ 6.1

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

That Awkward Moment

That Awkward Moment

2014 ★ 6.1

Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

Someone Like You...

Someone Like You...

2001 ★ 6.0

Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

Sleeping with Other People

Sleeping with Other People

2015 ★ 6.3

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.

Bye Bye Love

Bye Bye Love

1995 ★ 6.0

With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.

My Sassy Girl

My Sassy Girl

2008 ★ 6.7

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

¿Quieres ser mi hijo?

¿Quieres ser mi hijo?

2023 ★ 8.4

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.

Sex Appeal

Sex Appeal

2022 ★ 6.6

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.

Playing It Cool

Playing It Cool

2014 ★ 5.9

A young man meets and instantly falls in love with an engaged woman.

Friends with Benefits

Friends with Benefits

2011 ★ 6.6

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.

Zack and Miri Make a Porno

Zack and Miri Make a Porno

2008 ★ 6.3

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.

Desperados

Desperados

2020 ★ 6.0

A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.

Dean

Dean

2016 ★ 5.8

A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.

Players

Players

2024 ★ 6.1

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.

Bros

Bros

2022 ★ 6.7

Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.

How I Got Into College

How I Got Into College

1989 ★ 6.0

High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It won't be easy, since the college is highly selective and Marlon's grades are hardly impressive. That means the lovelorn teen will have to find a way to score high on the SATs and win over the college admissions committee.

The Moon Is Blue

The Moon Is Blue

1953 ★ 6.3

Two aging playboys are both after the same attractive young woman, but she fends them off by claiming that she plans to remain a virgin until her wedding night. Both men determine to find a way around her objections.

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