Movies like You, Me and Dupree (2006)
The best movies like You, Me and Dupree (2006) are I Love You, Man (2009), The Out-of-Towners (1999) and Barefoot in the Park (1967). If You, Me and Dupree hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Philadelphia Story (1940)7.5/10 from 1,045 votes
- NewestYoh! Bestie (2026)Released 2026
I Love You, Man (2009)
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."
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Out-of-Towners (1999)
The adventures of married couple Henry and Nancy Clark, vexed by misfortune while in New York City for Henry's job interview.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisBarefoot in the Park (1967)
In this film based on a Neil Simon play, newlyweds Corie, a free spirit, and Paul Bratter, an uptight lawyer, share a sixth-floor apartment in Greenwich Village. Soon after their marriage, Corie tries to find a companion for mother, Ethel, who is now alone, and sets up Ethel with neighbor Victor. Inappropriate behavior on a double date causes conflict, and the young couple considers divorce.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisMy Best Friend's Wedding (1997)
When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Midsummer Night's Sex Comedy (1982)
A nutty inventor, his frustrated wife, a philosopher cousin, his much younger fiancée, a randy doctor, and a free-thinking nurse spend a summer weekend in and around a stunning - and possibly magical - country house.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisKeeping the Faith (2000)
Best friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian's lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYes Man (2008)
Carl Allen, a guy whose life is going nowhere, signs up for a self-help program based on one simple covenant: say yes to everything…and anything.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThink Like a Man Too (2014)
All the couples are back for a wedding in Las Vegas, but plans for a romantic weekend go awry when their various misadventures get them into some compromising situations that threaten to derail the big event.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Wedding Singer (1998)
Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and Robbie meet and hit it off, they find that things are more complicated than anybody thought.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Philadelphia Story (1940)
When a rich woman's ex-husband and a tabloid-type reporter turn up just before her planned remarriage, she begins to learn the truth about herself.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisFever Pitch (2005)
Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Baxter (2005)
Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses and parents, Elliot is a perfectly nice guy. And that's his problem.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Other Woman (2014)
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-timing SOB.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSaving Silverman (2001)
A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisThe Wedding Date (2005)
With the wedding of her younger sister fast approaching, Kat Ellis faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey, the man who left her as they moved closer to marriage, happens to be the groom's best man. Determined to show everyone -- most of all Jeffrey -- that her romantic life is as full and thrilling as ever, Kat hires a charming male escort as her date.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisCousins (1989)
When Larry and Maria learn that their respective spouses are cheating on them, they try to turn the tables on them by pretending to have an affair. However, they soon find themselves falling in love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPeople We Meet on Vacation (2026)
Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisBachelor Party (1984)
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisWedding Bells (2016)
Nick and Molly, commitment-phobic and busy professionals with little in common, are asked to be the best man and maid of honor at the wedding of their mutual friends, Amy and Jamie.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisLady and the Tramp (1955)
Lady, a golden cocker spaniel, meets up with a mongrel dog who calls himself the Tramp. He is obviously from the wrong side of town, but happenings at Lady's home make her decide to travel with him for a while.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like thisSealed With a Kiss: Wedding March 6 (2021)
The modest wedding plans of a celebrity and his down-to-earth fiancée escalate while Mick gets an enticing opportunity Olivia won’t let him refuse, putting their own big day in jeopardy.
Why it matches: Similar story and style · both comedy & romance
George of the Jungle (1997)
Deep in the African jungle, a baby named George, the sole survivor of a plane crash, is raised by gorillas. George grows up to be a buff and lovable klutz who has a rainforest full of animal friends: Tookie, his big-beaked toucan messenger; Ape, a witty talking gorilla; and Shep, a peanut-loving pooch of an elephant. But when poachers mess with George's pals, the King of Swing swings into action.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisWedding Crashers (2005)
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.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisMystic Pizza (1988)
Three teenage girls come of age while working at a pizza parlor in Mystic, Connecticut.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisSingles (1992)
A group of young adults in their twenties, who share an apartment in the city of Seattle, ponder on love and face all the challenges of adulthood.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisWhite Men Can't Jump (1992)
Two street basketball hustlers try to con each other, then team up for a bigger score.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisFlickering Lights (2000)
Four small gangsters from Copenhagen trick a gangster boss: they take over 4,000,000 kroner which they were supposed to bring him. Trying to escape to Barcelona they are forced to stop in the countryside, in an old, wrecked house, hiding there for several weeks. Slowly, one after another, they realize, that they would like to stay there, start a new life.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisAre We Done Yet? (2007)
Newlyweds Nick and Suzanne decide to move to the suburbs to provide a better life for their two kids. But their idea of a dream home is disturbed by a contractor with a bizarre approach to business.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisCrazy/Beautiful (2001)
At Pacific Palisades High, a poor Latino falls hard for a troubled girl from the affluent neighborhood.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like You, Me and Dupree?
The closest matches to You, Me and Dupree are I Love You, Man (2009), The Out-of-Towners (1999) and Barefoot in the Park (1967). Below are 27 more, each with the reason it matches.
What should I watch after You, Me and Dupree?
Start with I Love You, Man (2009), the closest match to You, Me and Dupree.
What is the highest-rated movie like You, Me and Dupree?
The Philadelphia Story (1940), rated 7.5/10 by 1,045 TMDB users.
What is the newest movie like You, Me and Dupree?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like You, Me and Dupree?
Yes: I Love You, Man (2009), The Out-of-Towners (1999) and Barefoot in the Park (1967).
How are movies similar to You, Me and Dupree chosen?
First come films that Trakt’s viewers watch alongside You, Me and Dupree, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.