Movies Like An Unexpected Valentine

If you liked An Unexpected Valentine (2025), a tv movie and comedy movie directed by Michael Robison, 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
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…
2
The 27-Hour Day (2021)
★ 7.1/10Also tv movie and comedy
An entrepreneur takes a necessary break from developing her wellness brand empire and discovers that the work-life balance she needs won’t be easy. Will a new romance and relaxing retreat change her life forever?
3
Paris, Wine & Romance (2019)
★ 6.9/10Also romance and tv movie
Isabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in Paris. Upon arrival, Isabella meets…
4
Winter Castle (2019)
★ 6.8/10Also tv movie and romance
When Jenny attends her sister’s winter wedding at an ice hotel, her heart melts over the best man, the problem is he unexpectedly brings a “plus one,” seemingly dashing her hopes for a wintery romance.
5
Love on the Slopes (2018)
★ 6.4/10Also tv movie and romance
NYC-based copy editor, Alex, is sent to Ridgeline Resort, an extreme sports outpost, to write a story for a travel writing competition. At first, she fails at everything – much to the chagrin of Cole, an extreme sports…
6
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…
7
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.
8
All of My Heart: Inn Love (2017)
★ 6.8/10Also romance and tv movie
Brian and Jenny are preparing for the grand opening of their bed and breakfast, Emily's Country Inn, when a big storm hits Buck County. Brian agrees to go back to Wall Street to boost their funds, while Jenny scrambles…
9
Love in Winterland (2020)
★ 6.6/10Also tv movie and romance
Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.
10
Romance in Style (2022)
★ 6.6/10Also tv movie and comedy
Ella's unique designs inspire publishing mogul Derek to include plussized fashion in his magazine. It's not long before Derek realizes that Ella's influence reaches far beyond the catwalk.
11
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.
12
How to Fall in Love (2012)
★ 6/10Also comedy and romance
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…
13
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.
14
It Was Always You (2021)
★ 7.3/10Also romance and tv movie
Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.
15
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.
16
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.
17
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…
18
October Kiss (2015)
★ 6.5/10Also tv movie and comedy
Poppy Summerall is hired near Halloween as a temporary nanny by Ryan Lawson, a widowed, work-obsessed executive. Through a series of adventures, the eternally optimistic Poppy sets out to teach Ryan and his two young…
19
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…
20
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…