50 Movies Like The 40 Year Old Virgin (2005) You Need to Watch Next
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-obsesse
Updated June 2026
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If you loved The 40 Year Old Virgin (2005) by Judd Apatow, here are 50 movies that share its content DNA. iRankMovies measures real similarity using cosine similarity across eight weighted dimensions — genre (50%), tone (12%), pace (10%), structure (8%), era (7%), theme (6%), audience (4%) and narrative perspective (3%) — not just the rating. The closest matches according to our analysis are Zack and Miri Make a Porno, Overboard, Legally Blonde 2: Red, White & Blonde. Every title is ranked by how closely it matches and backed by the iRank Score, a composite of IMDb, Rotten Tomatoes, Metacritic and TMDb across 12,000+ analysed titles.
50 Movies Similar to The 40 Year Old Virgin
Zack and Miri Make a Porno
2008 · Kevin Smith
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
In common: Comedy · Romance
Overboard
2018 · Rob Greenberg
A spoiled, wealthy yacht owner is thrown overboard and becomes the target of revenge from his mistreated employee.
In common: Comedy · Romance
Legally Blonde 2: Red, White & Blonde
2003 · Charles Herman-Wurmfeld
Now a rising young lawyer, Elle Woods is about to make partner at her firm, but when she finds out her dog's relatives are being used as cosmetic test subjects, she heads to Washington D.C. to fight f
In common: Comedy · Romance
Upgraded
2024 · Carlson Young
Ana is an ambitious intern dreaming of a career in the art world while trying to impress her demanding boss Claire. When she's upgraded to first class on a work trip, she meets handsome Will, and Ana
In common: Comedy · Romance
Wedding Crashers
2005 · David Dobkin
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
In common: Comedy · Romance
Meet the Parents
2000 · Jay Roach
Greg Focker is ready to marry his girlfriend, Pam, but before he pops the question, he must win over her formidable father, humorless former CIA agent Jack Byrnes, at the wedding of Pam's sister. As G
In common: Comedy · Romance
There's Something About Mary
1998 · Peter Farrelly
For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including
In common: Comedy · Romance
A Family Affair
2024 · Richard LaGravenese
The only thing worse than being the assistant to a high-maintenance movie star who doesn't take you seriously? Finding out he's smitten with your mom.
In common: Comedy · Romance
The House Bunny
2008 · Fred Wolf
Shelley is living a carefree life until a rival gets her tossed out of the Playboy Mansion. With nowhere to go, fate delivers her to the sorority girls from Zeta Alpha Zeta. Unless they can sign a new
In common: Comedy · Romance
My Fair Lady
1964 · George Cukor
A snobbish phonetics professor agrees to a wager that he can take a flower girl and make her presentable in high society.
In common: Comedy · Romance
You've Got Mail
1998 · Nora Ephron
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.
In common: Comedy · Romance
Deuce Bigalow: Male Gigolo
1999 · Mike Mitchell
Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigol
In common: Comedy · Romance
What Women Want
2000 · Nancy Meyers
Advertising executive Nick Marshall is as cocky as they come, but what happens to a chauvinistic guy when he can suddenly hear what women are thinking? Nick gets passed over for a promotion, but after
In common: Comedy · Romance
Good Luck Chuck
2007 · Mark Helfrich
Cursed since childhood, dentist Charlie Logan 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
In common: Comedy · Romance
Trainwreck
2015 · Judd Apatow
Ever since her father drilled into her head that monogamy isn't realistic, magazine writer Amy has made promiscuity her credo. As much as she enjoys an uninhibited life free of commitment, Amy is real
In common: Comedy · Romance
Crazy Rich Asians
2018 · Jon M. Chu
An American-born Chinese economics professor accompanies her boyfriend to Singapore for his best friend's wedding, only to get thrust into the lives of Asia's rich and famous.
In common: Comedy · Romance
Serendipity
2001 · Peter Chelsom
Although strangers Sara and Jonathan are both already in relationships, they realize they have genuine chemistry after a chance encounter – but part company soon after. Years later, they each yearn to
In common: Comedy · Romance
I Now Pronounce You Chuck & Larry
2007 · Dennis Dugan
Firefighters Chuck Ford and Larry Valentine are guy's guys, loyal to the core—which is why when widower Larry asks Chuck to pose as his lover so that he can get domestic partner benefits for his kids,
In common: Comedy · Romance
Sweet Home Alabama
2002 · Andy Tennant
New York fashion designer, Melanie Carmichael suddenly finds herself engaged to the city's most eligible bachelor. But her past holds many secrets—including Jake, the redneck husband she married in hi
In common: Comedy · Romance
Runaway Bride
1999 · Garry Marshall
Having already left three grooms at the altar, Maggie Carpenter is branded "the runaway bride" by jaded New York journalist Ike Graham. But, after his facts are called into question, Ike races to Magg
In common: Comedy · Romance
Overboard
1987 · Garry Marshall
Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her m
In common: Comedy · Romance
The Ugly Truth
2009 · Robert Luketic
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
In common: Comedy · Romance
What Happens in Vegas
2008 · Tom Vaughan
During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then co
In common: Comedy · Romance
The Rebound
2009 · Bart Freundlich
Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Ara
In common: Comedy · Romance
Confessions of a Shopaholic
2009 · P.J. Hogan
In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite fashion magazine, bu
In common: Comedy · Romance
While You Were Sleeping
1995 · Jon Turteltaub
A transit worker pulls commuter Peter off railway tracks after he's mugged, but—while he's in a coma—his family mistakenly thinks she's Peter's fiancée, and she doesn't correct them. Things get more c
In common: Comedy · Romance
Little Fockers
2010 · Paul Weitz
It has taken 10 years, two little Fockers with wife Pam and countless hurdles for Greg to finally get in with his tightly wound father-in-law, Jack. After the cash-strapped dad takes a job moonlightin
In common: Comedy · Romance
Long Shot
2019 · Jonathan Levine
Journalist Fred Flarsky reunites with his childhood crush, Charlotte Field, now one of the most influential women in the world. As she prepares to make a run for the Presidency, Charlotte hires Fred a
In common: Comedy · Romance
The Birdcage
1996 · Mike Nichols
A gay cabaret owner and his drag queen partner agree to put up a false heterosexual front so that their son can introduce them to his fiancée's conservative parents.
In common: Comedy · Romance
Waiting...
2005 · Rob McKittrick
Young employees at Shenaniganz restaurant collectively stave off boredom and adulthood with their antics.
In common: Comedy · Romance
She's Out of My League
2010 · Jim Field Smith
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
In common: Comedy · Romance
She's All That
1999 · Robert Iscove
High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desper
In common: Comedy · Romance
Under the Tuscan Sun
2003 · Audrey Wells
Frances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in the Italian countrys
In common: Comedy · Romance
Sixteen Candles
1984 · John Hughes
With the occasion all but overshadowed by her sister's upcoming wedding, angst-ridden Samantha faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake, but worr
In common: Comedy · Romance
National Lampoon's Van Wilder
2002 · Walt Becker
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 com
In common: Comedy · Romance
The Other Woman
2014 · Nick Cassavetes
After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timi
In common: Comedy · Romance
MILF
2018 · Axelle Laffont
Three childhood friends - Elise, Sonia and Cecile - leave for a summer in the South of France to help clear Cecile’s holiday house before it is put up for sale. There, they soon become the prime targe
In common: Comedy · Romance
American Pie
1999 · Paul Weitz
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 themselve
In common: Comedy · Romance
Anyone But You
2023 · Will Gluck
After an amazing first date, Bea and Ben’s fiery attraction turns ice cold — until they find themselves unexpectedly reunited at a destination wedding in Australia. So they do what any two mature adul
In common: Comedy · Romance
The Parent Trap
1998 · Nancy Meyers
Hallie Parker and Annie James are identical twins who were separated at a young age due to their parents' divorce. Unbeknownst to their parents, the girls are sent to the same summer camp, where they
In common: Comedy · Romance
No Strings Attached
2011 · Ivan Reitman
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 frie
In common: Comedy · Romance
The Girl Next Door
2004 · Luke Greenfield
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 jeopardize
In common: Comedy · Romance
Blended
2014 · Frank Coraci
Recently divorced mom Lauren and widowed dad Jim let their friends push them into a blind date, which goes disastrously wrong. Unsurprisingly, neither wants to see the other ever again. However, fate
In common: Comedy · Romance
Amélie
2001 · Jean-Pierre Jeunet
At a tiny Parisian café, the adorable yet painfully shy Amélie accidentally discovers a gift for helping others. Soon Amelie is spending her days as a matchmaker, guardian angel, and all-around do-goo
In common: Comedy · Romance
Just Go with It
2011 · Dennis Dugan
While romancing Palmer, a much younger schoolteacher, plastic surgeon Danny Maccabee enlists his loyal assistant Katherine to pretend to be his soon to be ex-wife, in order to cover up a careless lie.
In common: Comedy · Romance
No Hard Feelings
2023 · Gene Stupnitsky
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leav
In common: Comedy · Romance
Mamma Mia!
2008 · Phyllida Lloyd
A spirited young bride-to-be living with her single mother on a small Greek island secretly invites three of her mother's ex-boyfriends in hope of finding her biological father to walk her down the ai
In common: Comedy · Romance
The Kissing Booth
2018 · Vince Marcello
When teenager Elle's first kiss leads to a forbidden romance with the hottest boy in high school, she risks her relationship with her best friend.
In common: Comedy · Romance
How to Lose a Guy in 10 Days
2003 · Donald Petrie
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy s
In common: Comedy · Romance
The Princess Diaries
2001 · Garry Marshall
A socially awkward but very bright 15-year-old girl being raised by a single mom discovers that she is the princess of a small European country because of the recent death of her long-absent father, w
In common: Comedy · Romance