Movies Like My Summer With Des

If you liked My Summer With Des (1998), a comedy and romance movie directed by Simon Curtis, 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
Prom Pact (2023)
★ 7.2/10Also comedy and romance
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…
2
The Seven Year Hitch (2012)
★ 6/10Also romance and comedy
Jennifer and Kevin are childhood best friends who have lived together, platonically, as adults for many years. When Jennifer decides to marry her cheating, manipulative boyfriend, Bryce Kevin has to stop the wedding to…
3
You Cast A Spell On Me (2015)
★ 6.8/10Also comedy and romance
Despite agreeing to an arranged marriage to a childhood friend, a successful businessman tries to track down a beautiful woman that he met at a Halloween party.
4
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
5
As Luck Would Have It (2021)
★ 6.5/10Also tv movie and comedy
When Lindsey travels to Ireland to acquire land that is perfect for a resort, she decides to enter the town's matchmaking festival to prove her investment—and win over a handsome local.
6
What's Love Got to Do with It? (2023)
★ 6.1/10Also romance and comedy
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
7
Perfect Match (2015)
★ 5.9/10Also comedy and romance
When an engaged couple can’t agree on anything, the mother of the groom hires a wedding planner and an event planner to help put together the wedding of their dreams. The two planners are as different as night and day…
8
Love Under the Stars (2015)
★ 6.5/10Also comedy and tv movie
Young at heart graduate student Becca strikes up an unlikely friendship with Emily, a quiet girl who recently lost her mother. With every passing play date chaperoned by Emily's father, Becca helps Emily come out of…
9
A Merry Christmas Wish (2022)
★ 5.9/10Also tv movie and comedy
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event…
10
Christmas on Windmill Way (2023)
★ 5.9/10Also romance and comedy
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas…
11
Let's Make Love (1960)
★ 6.4/10Also comedy and romance
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
12
Love Is in the Air (2023)
★ 6.2/10Also romance and comedy
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
13
My Favorite Wedding (2017)
★ 6.9/10Also comedy and romance
Potential Northwestern fellow Tess Harper lasers through her best friend's wedding planning like the star doctor she hopes to soon become. In fact, Tess puzzles through any problem - provided it's not her own. When she…
14
Zack and Miri Make a Porno (2008)
★ 6.3/10Also comedy and romance
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…
15
Christmas with You (2022)
★ 5.8/10Also romance and comedy
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
16
Christmas at the Drive-In (2022)
★ 5.8/10Also tv movie and comedy
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
17
Players (2024)
★ 6.1/10Also romance and comedy
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…
18
A Royal Date for Christmas (2023)
★ 5.8/10Also romance and comedy
Bella Sparks, owner of Bella’s Boutique, takes on a demanding new client named Stefan, who needs to be outfitted for a week of high-stakes meetings and events after his luggage goes missing. Imagine Bella’s reaction…
19
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.
20
Catering Christmas (2022)
★ 6.3/10Also tv movie and comedy
A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls…