Movies Like You, Me and Dupree

If you liked You, Me and Dupree (2006), a comedy and romance movie directed by Anthony Russo and Joe Russo, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
I Love You, Man (2009)
★ 6.6/10Also comedy and romance
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…
2
The Out-of-Towners (1999)
★ 5.8/10Also comedy and romance
The adventures of married couple Henry and Nancy Clark, vexed by misfortune while in New York City for Henry's job interview.
3
Barefoot in the Park (1967)
★ 7.1/10Also comedy and romance
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…
4
My Best Friend's Wedding (1997)
★ 6.6/10Also comedy and romance
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…
5
Yes Man (2008)
★ 6.7/10Also comedy and romance
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.
6
Keeping the Faith (2000)
★ 6.1/10Also comedy and romance
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…
7
Think Like a Man Too (2014)
★ 6.4/10Also comedy and romance
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.
8
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedy
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.
9
The Right Kind of Wrong (2013)
★ 5.9/10Also romance and comedy
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
10
The Wedding Singer (1998)
★ 6.8/10Also romance and comedy
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…
11
The Philadelphia Story (1940)
★ 7.5/10Also comedy and romance
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.
12
Fever Pitch (2005)
★ 6.2/10Also romance and comedy
Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.
13
The Other Woman (2014)
★ 6.4/10Also comedy and romance
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.
14
Saving Silverman (2001)
★ 5.8/10Also comedy and romance
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.
15
The Wedding Date (2005)
★ 6.8/10Also romance and comedy
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…
16
People We Meet on Vacation (2026)
★ 7/10Also comedy and romance
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.
17
The Rebound (2009)
★ 6.5/10Also romance and comedy
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 Aram to be her nanny…
18
Cousins (1989)
★ 6/10Also comedy and romance
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.
19
It Happened One Night (1934)
★ 7.8/10Also comedy and romance
A runaway heiress makes a deal with the rogue reporter trailing her but the mismatched pair end up stuck with each other when their bus leaves them behind.
20
The Baxter (2005)
★ 6/10Also comedy and romance
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…