Movies like My Summer With Des (1998)

Prom Pact (2023)

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 tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.

Why it matches: Recommended by TMDB viewers · both comedy & romance

You Cast A Spell On Me (2015)

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.

Why it matches: Recommended by TMDB viewers · both comedy & romance

How to Fall in Love (2012)

An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.

Why it matches: Recommended by TMDB viewers · both comedy & romance

Her Pen Pal (2021)

Event planner Victoria can’t wait to attend –- and plan –- her best friend’s wedding in Paris. But when she finds out her ex is bringing a date, Victoria reconnects with her French childhood pen pal.

Why it matches: Recommended by TMDB viewers · both romance & comedy

The Seven Year Hitch (2012)

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 protect her from making, what he believes is, a terrible mistake. With a little help from his brother and neighbor Kevin discovers that he and Jennifer are already legally married due to common law, having lived together for seven years and, as such, Jennifer can not marry Bryce.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Love Under the Stars (2015)

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 her shell and cope with her loss, and Emily teaches Becca to take on adult responsibilities. When a romance develops between Becca and Nate, though, the two must learn to balance their new relationship with Nate's responsibility to Emily, and with Becca's responsibility to finish her education.

Why it matches: Recommended by TMDB viewers · both comedy & romance

As Luck Would Have It (2021)

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.

Why it matches: Recommended by TMDB viewers · both comedy & romance

Holiday Harmony (2022)

A likeable and talented underdog gets momentarily sidelined from chasing her musical dreams when her van breaks down in a welcoming small town just before Christmas.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Christmas at the Drive-In (2022)

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.

Why it matches: Recommended by TMDB viewers · both comedy & romance

A Merry Christmas Wish (2022)

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, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.

Why it matches: Recommended by TMDB viewers · both comedy & romance

Perfect Match (2015)

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, but as they too learn to compromise, they discover opposites do indeed attract and can combine to produce incredible results!

Why it matches: Recommended by TMDB viewers · both comedy & romance

My Boyfriends' Dogs (2014)

The owners of a small diner are surprised one rainy evening when, just after close, a young woman wearing a wedding dress with three dogs in tow begs to come into their restaurant. What follows is the young woman's retelling of how she arrived at this curious junction in her life and how, through the search for the right man, she ended up as a runaway bride with three new dogs.

Why it matches: Recommended by TMDB viewers · both comedy & romance

Sister of the Bride (2019)

After only 6 months of dating, Stephanie and Ben get engaged and are delighted to share the news. However, they hit a road bump when Stephanie’s parents show concern that the couple has moved too fast.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Christmas on Windmill Way (2023)

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 bread. But Mia's world is rocked when she learns that Ann was having financial troubles and had to sell the land deed to the Windmill Way property in her family for generations. Making matters worse, the buyer is Mia's former boyfriend, property developer Brady Schaltz, who must let Mia and Ann know the Meijer family-owned heritage Dutch sawmill, renowned for the past 90 years for its fine millwork and beautiful wooden furniture, will be torn down to put up a luxurious resort.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Surprised by Love (2015)

The story of a young businesswoman who tries to convince her uptight parents to accept her current boyfriend and instead finds herself falling for an old high school flame.

Why it matches: Recommended by TMDB viewers · both romance & comedy

My Favorite Wedding (2017)

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 meets divorce lawyer and groom's best friend, Michael, Tess maneuvers around him like a gurney in the emergency room until she discovers this best man has a few moves of his own.

Why it matches: Recommended by TMDB viewers · both comedy & romance

Never Kiss a Man in a Christmas Sweater (2020)

Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Holiday Date (2019)

When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend.

Why it matches: Recommended by TMDB viewers · both romance

What's Love Got to Do with It? (2023)

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.

Why it matches: Recommended by TMDB viewers · both romance & comedy

The Wrong Paris (2025)

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.

Why it matches: Recommended by TMDB viewers · both romance & comedy

Pickled (2022)

A new sport will get its close-up with a tournament of all-star teams battling it out for charity and a chance to win the coveted Golden Gherkin.

Why it matches: Similar story and style · both comedy

Mr. Woodcock (2007)

Taken aback by his mother's wedding announcement, a young man returns home in an effort to stop her from marrying his old high school gym teacher, a man who made high school hell for generations of students.

Why it matches: Similar story and style · both comedy & romance

Fever Pitch (1997)

A romantic comedy about a man, a woman and a football team. Based on Nick Hornby's best selling autobiographical novel, Fever Pitch. English teacher Paul Ashworth believes his long standing obsession with Arsenal serves him well. But then he meets Sarah. Their relationship develops in tandem with Arsenal's roller coaster fortunes in the football league, both leading to a nail biting climax.

Why it matches: Similar story and style · both comedy & romance

Tin Cup (1996)

A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.

Why it matches: Similar story and style · both romance & comedy

Cinderella Man (2005)

The true story of boxer Jim Braddock who, following his retirement in the 1930s, makes a surprise comeback in order to lift his family out of poverty.

Why it matches: Similar story and style · both romance

The Wild Soccer Bunch 4 (2007)

With the victory against "The Beastly Beasts", "The Wild Soccer Bunch" showed it to everyone and then won every single game. Only one victory now separates them from the "Pott", the Freestyle Soccer Cup. For this they have to compete against the "Wolves of Ragnarök". But the wolves are not normal opponents! They have a dark secret - and behind them lurks a power stronger than all of them: the girl Horizon and the "Silver Lights" from the fog...

Why it matches: Similar story and style · both comedy

Lucky You (2007)

A professional poker player whose astounding luck at the table fails to translate into his lonesome love life attempts to win the World Series of Poker while simultaneously earning the affections of a beautiful Las Vegas singer.

Why it matches: Similar story and style · both romance

Deadspiel (2008)

Ghoulishly funny. this short follows a curling match between humans and zombies who must choose between sportsmanship and bloodsport.

Why it matches: Similar story and style · both comedy

Τα ντερέκια (1987)

Why it matches: Similar story and style · both comedy

Bad News Bears (2005)

Morris Buttermaker is a burned-out minor league baseball player who loves to drink and can't keep his hands to himself. His long-suffering lawyer arranges for him to manage a local Little League team, and Buttermaker soon finds himself the head of a rag-tag group of misfit players. Through unconventional team-building exercises and his offbeat coaching style, Buttermaker helps his hapless Bears prepare to meet their rivals, the Yankees.

Why it matches: Similar story and style · both comedy