Movies Like The Holiday Proposal Plan

If you liked The Holiday Proposal Plan (2023), a tv movie and comedy movie directed by Jake Helgren, 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
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…
2
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…
3
The Mistle-Tones (2012)
★ 6.1/10Also tv movie and comedy
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…
4
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…
5
12 Gifts of Christmas (2015)
★ 6.1/10Also tv movie and comedy
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…
6
Christmas at Grand Valley (2018)
★ 6.4/10Also tv movie and romance
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…
7
Christmas in Evergreen: Letters to Santa (2018)
★ 6.8/10Also romance and tv movie
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.
8
A Christmas Kiss II (2014)
★ 5.8/10Also tv movie and romance
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…
9
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.
10
Christmas Made to Order (2018)
★ 6.1/10Also tv movie and romance
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…
11
Christmas in Evergreen: Tidings of Joy (2019)
★ 6.8/10Also romance and tv movie
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.
12
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy and tv movie
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
13
'Twas the Text Before Christmas (2023)
★ 6.5/10Also romance and comedy
Addie is a New York City chiropractor mistakenly receives a text from “Nana.” The accidental text turns into a loving friendship between the matronly Nana and Addie who now communicate regularly. Nana invites Addie to…
14
A Timeless Christmas (2020)
★ 6.4/10Also romance and tv movie
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.
15
Chateau Christmas (2020)
★ 6.1/10Also romance and tv movie
Margot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.
16
Kristin's Christmas Past (2013)
★ 5.9/10Also tv movie and comedy
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…
17
Write Before Christmas (2019)
★ 6.9/10Also tv movie and romance
A recently single Jessica sends Christmas cards to people who have impacted her life—the aunt who raised her, her younger brother in the military, a popstar who was part of the soundtrack of her life, the music teacher…
18
A Cookie Cutter Christmas (2014)
★ 6.1/10Also tv movie and comedy
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…
19
A Christmas Prince: The Royal Baby (2019)
★ 6.3/10Also romance and tv movie
Christmas brings the ultimate gift to Aldovia: a royal baby. But first, Queen Amber must help her family and kingdom by finding a missing peace treaty.
20
Never Kiss a Man in a Christmas Sweater (2020)
★ 6.5/10Also romance and comedy
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.