Best movies like The 40-Year-Old Virgin

Similar in 81%

Dinner for Schmucks (2010)

Plot Summary:

Rising executive Tim Wagner works for a boss who hosts a monthly dinner in which the guest who brings the biggest buffoon gets a career-boost. Tim plans on not attending until he meets Barry, a man who builds dioramas using stuffed mice. Barry's blundering but good intentions send Tim's life into a downward spiral, threatening a major business deal and possibly scuttling Tim's engagement to his fiancee.

Similar in 85%

Sex Ed (2014)

Plot Summary:

Eddie lands his first teaching gig at an inner city middle school and finds his highly pubescent pupils are receiving no form of sexual education. Eddie isn't really equipped to teach them...he's not exactly experienced romantically.

Similar in 82%

Wanderlust (2012)

Plot Summary:

Rattled by sudden unemployment, a Manhattan couple surveys alternative living options, ultimately deciding to experiment with living on a rural commune where free love rules.

Similar in 83%

Miss March (2009)

Plot Summary:

A young man awakens from a four-year coma to hear that his once virginal high-school sweetheart has since become a centerfold in one of the world's most famous men's magazines. He and his sex-crazed best friend decide to take a cross-country road trip in order to crash a party at the magazine's legendary mansion headquarters and win back the girl.

Similar in 88%

Sex Tape (2014)

Plot Summary:

When Jay and Annie first got together, their romantic connection was intense – but ten years and two kids later, the flame of their love needs a spark. To kick things up a notch, they decide – why not? – to make a video of themselves trying out every position in The Joy of Sex in one marathon three-hour session. It seems like a great idea – until they discover that their most private video is no longer private. With their reputations on the line, they know they’re just one click away from being laid bare to the world... but as their race to reclaim their video leads to a night they'll never forget, they'll find that their video will expose even more than they bargained for.

Similar in 84%

Good Luck Chuck (2007)

Plot Summary:

Cursed since childhood, dentist Charlie Kagan cannot find the right woman. Even worse, he learns that each of his ex-girlfriends finds true love with the man she meets after her relationship with him ends. Hearing of Charlie's reputation as a good-luck charm, women from all over line up for a quick tryst. But when Charlie meets the woman of his dreams, he must find a way to break the curse or risk losing her to the next man she meets.

Similar in 88%

National Lampoon's Van Wilder (2002)

Plot Summary:

Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuition fees, Van must come up with the money if he wants to stay in college, so he and his friends come up with a great fund-raising idea – throwing parties. However, when the college magazine finds out and reporter, Gwen is sent to do a story on Van Wilder, things get a little complicated.

Similar in 84%

I Love You, Man (2009)

Plot Summary:

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates.".

Similar in 86%

Hall Pass (2011)

Plot Summary:

When best buds Rick and Fred begin to show signs of restlessness at home, their wives take a bold approach to revitalize their marriages: they grant the guys a "hall pass", one week of freedom to do whatever they want. At first, it seems like a dream come true, but they quickly discover that their expectations of the single life - and themselves - are completely and hilariously out of sync with reality.

Similar in 77%

Knocked Up (2007)

Plot Summary:

For fun loving party animal Ben Stone, the last thing he ever expected was for his one night stand to show up on his doorstep eight weeks later to tell him she's pregnant.

Similar in 85%

There's Something About Mary (1998)

Plot Summary:

Having never fully recovered from a prom date that became a total disaster, a man finally gets a chance to reunite with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.

Similar in 81%

The To Do List (2013)

Plot Summary:

Feeling pressured to become more sexually experienced before she goes to college, Brandy Klark makes a list of things to accomplish before hitting campus in the fall.

Similar in 86%

Road Trip (2000)

Plot Summary:

Four friends take off on an 1800 mile road trip to retrieve an illicit tape mistakenly mailed to a girl friend.

Similar in 82%

Sex Drive (2008)

Plot Summary:

A high school senior drives cross-country with his best friends to hook up with a babe he met online.

Similar in 75%

Zack and Miri Make a Porno (2008)

Plot Summary:

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.

Similar in 87%

The Rebound (2009)

Plot Summary:

Sandy, upon discovering her husband's infidelity while watching her son's birthday video, leaves the suburbs and moves into the city. She gets an apartment that's above a coffee house where she befriends one of the workers, Aram, a guy whose wife only married him so she could get a green card. Aram's family thinks he's wasting his life and education by working in the coffee house. Soon after moving into the apartment, Sandy hires Aram to be her nanny while she takes on work for the first time since her children where born. It isn't long when Aram and Sandy find they get along wonderfully and start to date. But the question is: is their relationship real or is it, in fact, just a rebound for both of them?.

Similar in 84%

No Strings Attached (2011)

Plot Summary:

Emma is a busy doctor who sets up a seemingly perfect arrangement when she offers her best friend Adam a relationship with one rule: No strings attached. But when a fling becomes a thing, can sex friends stay best friends?.

Similar in 76%

Forgetting Sarah Marshall (2008)

Plot Summary:

When Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend suggests that Peter should get away from everything and to fly off to Hawaii to escape all his problems. After arriving in Hawaii and meeting the beautiful Rachel Jansen, Peter is shocked to see not only Aldous Snow in Hawaii, but also Sarah Marshall.

Similar in 84%

The Girl Next Door (2004)

Plot Summary:

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

Similar in 89%

American Pie (1999)

Plot Summary:

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.

Similar in 86%

What's Your Number? (2011)

Plot Summary:

Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

Similar in 76%

My Best Friend's Girl (2008)

Plot Summary:

When Dustin's girlfriend, Alexis, breaks up with him, he employs his best buddy, Tank, to take her out on the worst rebound date imaginable in the hopes that it will send her running back into his arms. But when Tank begins to really fall for Alexis, he finds himself in an impossible position.

Similar in 86%

She's Out of My League (2010)

Plot Summary:

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.

Similar in 89%

Just Go with It (2011)

Plot Summary:

A plastic surgeon, romancing a much younger schoolteacher, enlists his loyal assistant to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, the assistant's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.

Similar in 79%

Wedding Crashers (2005)

Plot Summary:

John and his buddy, Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the romantic day with a random hook-up. But when John meets Claire, he discovers what true love – and heartache – feels like.

Similar in 82%

That Awkward Moment (2014)

Plot Summary:

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.

Similar in 90%

The Ugly Truth (2009)

Plot Summary:

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.

Similar in 87%

Friends with Benefits (2011)

Plot Summary:

Jamie is a New York-based executive recruiter who entices Dylan, an art director from Los Angeles, to take a job at the New York office of GQ magazine. Finding that they have much in common, the two become fast friends. Feeling jaded by a number of broken romances, Dylan and Jamie decide that they are ready to quit looking for true love and focus on having fun. However, complications unfold when the two best pals add sex to their relationship.

Similar in 81%

Superbad (2007)

Plot Summary:

High school best buddies are facing separation anxiety as they prepare to go off to college. While attempting to score alcohol for a party with help from a fake ID-toting friend, the guys' evening takes a turn into chaotic territory.

Similar in 82%

Hitch (2005)

Plot Summary:

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.