The 40 Year Old Virgin
Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.
Movies Like The 40 Year Old Virgin
Similar in style, tone, and themes — find your next watch.
Another Gay Movie
2006★ 5.9
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
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
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.
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...
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
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.
¿Quieres ser mi hijo?
2023★ 8.5
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.
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.
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
2014★ 5.8
A young man meets and instantly falls in love with an engaged woman.
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.
My Sassy Girl
2008★ 6.8
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
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
2022★ 6.6
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
Sex Drive
2008★ 6.4
A high school senior drives cross-country with his best friends to hook up with a babe he met online.
A Nice Girl Like You
2020★ 5.8
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Maintenance Required
2025★ 6.1
Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking comfort, she turns to an anonymous online confidant - unaware she's confiding in Beau, the very rival threatening her business. As sparks fly both online and off, the truth threatens to blow everything apart.
The Ugly Truth
2009★ 6.5
A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.
How to Date Billy Walsh
2024★ 6.4
Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.
About Last Night
2014★ 6.0
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.