Movies Like Holiday Date
If you loved Holiday Date's Romance and TV Movie storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks

A Valentine's Match
Fired from her job as a reality TV host, Natalie returns home for Valentine's Day, only to find herself running the town festival's auction with her ex-fiancé thanks to two scheming mothers.

Sister of the Bride
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.

Stranded in Paradise
When a driven HR exec loses her high-powered job, she travels to Puerto Rico in an attempt to save her career at a business conference. But as the trip quickly becomes a disaster and a hurricane shuts down the whole island, she meets a handsome world traveler who gives her a new perspective on finding passion in life and love.

Winter Castle
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.

Lovely, Still
A holiday fable that tells the story of an elderly man discovering love for the first time.

Hitch
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.

A Glenbrooke Christmas
As Christmas nears, heiress Jessica Morgan seizes what seems like her last chance to experience a relaxed Christmas and heads off to the small town of Glenbrooke, where she meets a handsome fireman.

Home for Christmas Day
Jane is a single mother dead set on protecting her teenage daughter Betsy from the harsh realities of life. When Betsy falls in love with an enlisted man, Jane tries her best to steer Betsy away from heartache. Little does Jane realize she and her daughter are about to learn important lessons of the heart and that taking chances can sometimes lead to the most extraordinary happy endings.
More Movies Like Holiday Date

Sailing Into Love
A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town of Willow Bay.

Finding Christmas
Single mother Ryan has just about given up on dating after her divorce, happily accepting her young son as the most important man in her life. That all changes when Ryan's brother Owen, also feeling unlucky in love after a bad breakup, swaps his home in their small North Carolina town with New York City adman Sean.

A Christmas Princess
A struggling chef living in a trendy New York borough, Jessica took over a small restaurant where she used to work as a waitress, but it’s growing tough to make ends meet. Prince Jack, who’s in the city for his family’s annual Christmas charity dinner, finds himself in need of a last-minute chef for the royal event when he meets Jessica. As their relationship evolves and a romance blooms, so do the obstacles. But as the event arrives, she decides to go through with the dinner, and may just get the best Christmas present of all… love.

Love in the Forecast
After swearing off dating for a full year, Leah quickly learns her new commitment has made her a magnet for men.

Northanger Abbey
A young woman's penchant for sensational Gothic novels leads to misunderstandings in the matters of the heart.

A Prince in Paradise
Olivia, struggling with writer's block after a break up, takes a tropical holiday in hope of some inspiration and meets Prince Alexander, who needs some distance from his duty to marry royalty.

My Christmas Inn
With the holiday season in full swing, Jen Taylor is about to score a big promotion at the San Francisco ad agency where she works. But her life is unexpectedly turned upside down when she inherits a cozy inn in Alaska from her aunt. When she goes to inspect the property and meets handsome town attorney Steve Anderson, she's surprised to find that nothing is what she expected. The small town community is full of fun and festive Christmas traditions and soon, Jen starts wondering if the inn might just be the place she belongs, and if Steve could be the Mr. Right she has been waiting for.

A Christmas Prince: The Royal Baby
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.

A Royal Runaway Romance
Princess Amelia of Bundbury travels across America to explore a budding romance with an artist, only to fall in love with her bodyguard, Grady.

Love and Sunshine
Ally Craig has been fostering retired military dog, Sunshine, as she recovers from a broken engagement. But sparks fly again when Sunshine's military partner, Jake Terry, returns to claim the dog.

Beauty and the Billionaire
Addison travels with a picky billionaire as an assistant in her brother's place so he doesn't lose his job. She clashes with the billionaire until both start to see more in each other than they thought.

All of My Heart: The Wedding
Brian and Jenny are planning their wedding at the Inn where they fell in love. When a distant relative arrives and stakes their claim to the Inn, Brian and Jenny must find a way to save their beloved Inn or risk having to sell.
Why These Movies Are Similar
These recommendations share core qualities with Holiday Date (2019): Romance and TV Movie themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Holiday Date.
See full details for Holiday Date (2019)