Movies like The Holiday Proposal Plan (2023)
The best movies like The Holiday Proposal Plan (2023) are Catering Christmas (2022), The Mistle-Tones (2012) and Christmas on Windmill Way (2023). If The Holiday Proposal Plan hooked you with its tv movie and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedTrading Places (1983)7.2/10 from 3,844 votes
- NewestTinsel Town (2025)Released 2025
Catering Christmas (2022)
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 for Jean’s nephew, Carson, 30s, a travel photographer with no desire to take over the family’s foundation… until his aunt assigns him to the task of making sure the catered dinner goes perfectly.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Mistle-Tones (2012)
Holly, blessed with an amazing singing voice, is all set to audition for the newly vacated spot in a legendary local Christmas group which was founded by her late mother years ago. Shocked and upset when the slot goes to the barely talented best friend of the group's leader, Marci, Holly sets out to create her own musical group, The Mistle-Tones. After challenging their rivals to a sing-off on Christmas Eve, Holly finds herself on a journey to the real meaning of Christmas with some new friends and a new love thrown in for good measure.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChristmas 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
SnoozefestMovies like thisA 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
SnoozefestMovies like thisNever 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
Popcorn FlickMovies like thisChristmas 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
SnoozefestMovies like this12 Gifts of Christmas (2015)
When Anna Parisi, an unemployed fine arts painter, is unable to make ends meet, she is hired to become a personal Christmas shopper for Marc, an uptight corporate exec. As they begin working together, Marc learns that Christmas giving has less to do with the amount of money spent and more to do with the importance of the gift, while Anna discovers she might find success as an artist in a way she never expected. The best gift of all of course is the love they discover with one another.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Cookie Cutter Christmas (2014)
Two longtime rivals and elementary school teachers duke it out during the holidays in a Christmas cookie bake-off, but their real feud ignites over a shared interest in a handsome single dad. With both determined to win the prize and the romance, their competitiveness could jeopardize what matters most this Christmas season.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisJingle Around the Clock (2018)
Elle decides to reunite her college friends for Christmas, but her plans are thwarted by an opportunity at work to spearhead a Christmas campaign relaunch. She's forced to team up with ad campaign "fixer" Max, who has a completely different take on the holidays. As the two work together, they find themselves falling for each other. With the help of a little Christmas magic, will Elle pull off the perfect Christmas reunion and find the love she’s been searching for?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Kindhearted Christmas (2021)
Jamie owns a sightseeing and tour company in the small town of Cooperville, New York. Navigating the holidays with enthusiasm is trickier for Jamie since her husband Matt passed. Matt loved Christmas and found unparalleled joy in giving to others. While reminiscing with family, Jamie realizes the town desperately needs someone with Matt’s genius for thinking of the small gestures that bring genuine happiness to the holidays.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisKristin's Christmas Past (2013)
Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her life, she attempts to fix past mistakes, only to discover surprising truths about her family that may help her mend her present-day relationships.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisChristmas in Evergreen: Letters to Santa (2018)
Lisa's trip home to Evergreen for the holidays finds her shepherding an effort to save the town's beloved general store, fulfilling the wishes of a Christmas past and finding a romance full of Christmas magic.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Christmas Kiss II (2014)
At a Christmastime event, Jenna shares an impromptu, unforgettable kiss with the dashing billionaire, Cooper Montgomery. Unaware of his intentions and fearful of getting hurt in another relationship, Jenna vows to resist his charms, but begins to realize his affection is real as the two spend more time together.
Why it matches: Recommended by TMDB viewers · both romance
SnoozefestMovies like thisGood Morning Christmas! (2020)
Two competing TV hosts are sent to a festive small town over Christmas. While pretending to get along for the sake of appearances, they discover that there’s more to each other than they thought.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Timeless Christmas (2020)
Charles Whitley travels from 1903 to 2020 where he meets Megan Turner, a tour guide at his historic mansion, and experiences a 21st Century Christmas.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas at Grand Valley (2018)
Burned out from the hubbub of the Chicago gallery world, artist Kelly returns home to the picturesque Grand Valley just in time for Christmas. Leo, businessman and all-star dad to his children, struggles to balance his time this holiday season. When he is assigned to review a hotel in Grand Valley for its value, he sees this as the perfect opportunity for a Christmas family vacation. It isn’t long until Kelly and Leo’s worlds collide.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas Under the Stars (2019)
When Nick is fired from his high-powered investment firm at Christmastime, he takes a job at a Christmas tree lot. There, he meets Julie, an astronomy teacher who’s always looked to the stars for hope. As the Christmas spirit washes over him—and he begins falling for Julie—the once self-centered Nick discovers the joy of helping others.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas in Evergreen: Tidings of Joy (2019)
A skeptical writer shows up in Evergreen to get the scoop on the town's famed passion for Christmas during a search for a long-lost time capsule.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas Made to Order (2018)
When architect and Christmas amateur Steven finds himself hosting his family for Christmas, he recruits holiday coordinator Gretchen to bring holiday joy to his home. Gretchen’s expert Christmas spirit brings Steven’s family together, but neither expected it to bring them closer to each other. After a great opportunity presents itself to Gretchen, she and Steven must decide what’s really important in life.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisFive Star Christmas (2020)
After moving back to her hometown, Lisa (Lenz) plots with her siblings and grandparents to help her father's bed and breakfast get a five-star review from an incognito travel critic (Webster), but ends up falling for him, not knowing he is the real critic.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisSnowed in for Christmas (2021)
Kaley, a young Au Pair, finds herself unable to return home for the holidays when a snowstorm derails her plans. In spite of her own disappointment she is determined to teach the girls she watches, alongside their charming Uncle, the magic of Christmas. Will this series of events lead to a perfect Christmas?
Why it matches: Similar story and style · both comedy & romance
Mistletoe & Menorahs (2019)
When a determined toy company executive, Christy, must learn about Hanukkah in a hurry in order to land a big account, she enlists the help of her co-worker's friend Jonathan, who happens to also be in desperate need of turning his bachelor pad into a Christmas Wonderland to impress his girlfriend's father.
Why it matches: Similar story and style · both romance & comedy
The Princess Switch: Switched Again (2020)
When Duchess Margaret unexpectedly inherits the throne & hits a rough patch with Kevin, it’s up to Stacy to save the day before a new lookalike — party girl Fiona — foils their plans.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisWhile You Were Sleeping (1995)
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 complicated when she falls for his brother, who's not quite sure that she's who she claims to be.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like thisŚwięta inaczej (2022)
Fed up with forced cheer, twelve-dish feasts and predictable gifts, one person rejects the usual Christmas ritual and flees to the unknown, finally doing what they truly desire instead of what they must. This holiday, nothing will be the same: the world turns upside down and even the wildest dreams may come true.
Why it matches: Similar story and style · both romance & comedy
Tinsel Town (2025)
A washed-up Hollywood action hero is tricked into starring in a small English town’s chaotic Christmas pantomime, where a straight-talking dance instructor and his estranged daughter just might help him rediscover the magic of the season.
Why it matches: Similar story and style · both comedy & romance
Summer Storm (2004)
Tobi and Achim, the pride of the local crew club, have been the best of friends for years and are convinced that nothing will ever stand in the way of their friendship. They look forward to the upcoming summer camp and the crew competition. Then the gay team from Berlin arrives and Tobi is totally confused. The evening before the races begin, the storm that breaks out is more than meteorological.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisVeggieTales: An Easter Carol (2004)
Ebenezer Nezzer is out of control! He's trying to make Easter bigger than ever by filling London with plastic eggs! But just how hard can his mechanical chickens work before they're… well, fried? In just one unforgettable day and night, Cavis and Millward (Bob and Larry) and a music box angel named Hope must convince Nezzer that Easter is about more than candy and eggs. Inspired by Dickens' Christmas classic, this very special VeggieTales film explains why millions of Christians around the world celebrate Easter past, present and future.
Why it matches: Similar story and style · both comedy
Trading Places (1983)
A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisChristmas Coupon (2019)
Alison Grant begins teaching ice skating students on a friend's frozen pond after being fired from her rink job. On the first day of class her old high school sweetheart and now famous hockey player, Ivan Hall, unexpectedly shows up when he brings his niece for her skating lessons. While an initially cold reunion ensues, eventually Alison warms up to Ivan again.
Why it matches: Similar story and style · both romance
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Frequently asked questions
What are the best movies like The Holiday Proposal Plan?
The closest matches to The Holiday Proposal Plan are Catering Christmas (2022), The Mistle-Tones (2012) and Christmas on Windmill Way (2023). Below are 27 more, each with the reason it matches.
What should I watch after The Holiday Proposal Plan?
Start with Catering Christmas (2022), the closest match to The Holiday Proposal Plan.
What is the highest-rated movie like The Holiday Proposal Plan?
Trading Places (1983), rated 7.2/10 by 3,844 TMDB users.
What is the newest movie like The Holiday Proposal Plan?
Tinsel Town (2025) is the most recent release on this list.
Are there English movies like The Holiday Proposal Plan?
Yes: Catering Christmas (2022), The Mistle-Tones (2012) and Christmas on Windmill Way (2023).
How are movies similar to The Holiday Proposal Plan chosen?
First come films that Trakt’s viewers watch alongside The Holiday Proposal Plan, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.