Movies Similar to Holidate (2020)

30 items, 996 votes
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Little Italy (2018)

Starring: Emma Roberts, Hayden Christensen, Danny Aiello, Andrea Martin
Duration: 1h 42mins
Genres: Comedy, Romance

Nikki and Leo both grow up in Toronto's Little Italy neighborhood, where their families are running a pizza business together.
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Valentine's Day (2010)

Starring: Julia Roberts, Jamie Foxx, Anne Hathaway, Jessica Alba
Duration: 2h 5mins
Genres: Comedy, Romance

The film follows a group of related characters and their struggles with love on Valentine's Day.
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A Christmas in Tennessee (2018)

Starring: Rachel Boston, Andrew W. Walker, Patricia Richardson, Kate Moyer
Duration: 1h 27mins
Genres: Comedy, Family, Romance

Cutting short her French pastry training, divorced Allison Brentley and her adolescent daughter Olivia Brentley moved back to Allison's hometown of White Pines, Tennessee - nestled in the Smoky Mountains - when her father fell ill, and upon his subsequent death, Allison took over running the struggling family business, Rocky Top Bakery, working alongside her mother, Martha.
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A Brush with Love (2019)

Starring: Arielle Kebbel, Nick Bateman, Matthew James Dowden, Hilary Jardine
Duration: 1h 24mins
Genres: Romance

Jamie Spellman owns and operates Canvas Creations, a youth art school, in Seattle, she encouraging her students to transfer what is in their hearts to the canvas.
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How to Lose a Guy in 10 Days (2003)

Starring: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Duration: 1h 56mins
Genres: Comedy, Romance

Andie Anderson (Kate Hudson) is a writer for the women's magazine Composure as the "How to", subject-matter expert.
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Just Friends (2005)

Starring: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein
Duration: 1h 36mins
Genres: Comedy, Romance

In 1995, Chris Brander (Ryan Reynolds) is an overweight high school senior who secretly has a huge romantic crush on his classmate and best friend Jamie Palamino (Amy Smart).
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Trading Christmas (2011)

Starring: Tom Cavanagh, Faith Ford, Gil Bellows, Gabrielle Miller
Duration: 1h 27mins
Genres: Comedy, Romance

Three years after her husband died, Emily Spengler (Faith Ford), a 2nd grade teacher in the small Washington town of South Woodbourne, is preparing for the arrival of her daughter, Heather (Emma Lahana), who is attending school at Boston College.
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No Sleep 'til Christmas (2018)

Starring: Odette Annable, Dave Annable, Jess Salgueiro, Brittany Bristow
Duration: 1h 30mins
Genres: Comedy, Romance

A bartender and a businesswoman find they only have one thing in common; insomnia.
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Set It Up (2018)

Starring: Zoey Deutch, Glen Powell, Lucy Liu, Taye Diggs
Duration: 1h 45mins
Genres: Comedy, Romance

Harper Moore is the 25-year-old assistant to Kirsten Stevens, a former journalist and now editor of an online sports journalism empire.
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Moonlight in Vermont (2017)

Starring: Lacey Chabert, Carlo Marks, Jesse Moss, Fiona Vroom
Duration: 1h 23mins
Genres: Comedy, Romance

Moonlight in Vermont is the title of a 1943 American musical dramatic film. Vermont farm girl Gwen Harding goes a dance school in the city. She becomes semi-popular.
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It's Beginning to Look a Lot Like Christmas (2019)

Starring: Tricia Helfer, Eric Mabius, Aliza Vellani, Raf Rogers
Duration: 1h 23mins
Genres: Comedy

"It's Beginning to Look a Lot Like Christmas" is a Christmas song written in 1951 by Meredith Willson.
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In Search of a Midnight Kiss (2007)

Starring: Scoot McNairy, Sara Simmonds, Brian McGuire, Kathleen Luong
Duration: 1h 30mins
Genres: Comedy, Romance

Wilson (Scoot McNairy), a 29-year-old man who has just endured the most miserable year of his life, newly arrived in the City of Angels, is alone and penniless as New Year's Eve approaches.
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The Wedding Date (2005)

Starring: Dermot Mulroney, Debra Messing, Jack Davenport, Amy Adams
Duration: 1h 30mins
Genres: Comedy, Romance

Kat Ellis (Debra Messing) is a single New Yorker who returns to her parents' house in London to be the maid of honor at her younger half sister Amy's (Amy Adams) wedding.
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The Holiday (2006)

Starring: Kate Winslet, Cameron Diaz, Jude Law, Jack Black
Duration: 2h 16mins
Genres: Comedy, Romance

Iris Simpkins, a society columnist for The Daily Telegraph in London, still loves her ex-boyfriend, Jasper Bloom, despite the fact that he cheated on her and is emotionally needy.
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A December Bride (2016)

Starring: Jessica Lowndes, Daniel Lissing, Jay Hindle, Pauline Egan
Duration: 1h 24mins
Genres: Comedy, Romance

Aspiring interior designer Layla O'Reilly is dreading the Christmastime wedding of her cousin who's marrying Layla's ex-fiancé.
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A Christmas Arrangement (2018)

Starring: Nicky Whelan, Miles Fisher, Daphne Zuniga, Julie McNiven
Duration: 1h 30mins
Genres: Comedy, Romance

A flower shop owner enters the local Holiday Floral Show in an effort to win a cash prize to help keep her struggling business afloat, but she starts to fall for one of her direct competitors.
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Christmas Made to Order (2018)

Starring: Alexa PenaVega, Jonathan Bennett, Jo Marie Payton, Jacob Young
Duration: 2h 0mins
Genres: Romance

"When architect and Christmas amateur Steven (Jonathan Bennett) finds himself hosting his family for Christmas, he recruits holiday coordinator Gretchen (Alexa PenaVega) to bring holiday joy to his home.
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My Favorite Wedding (2017)

Starring: Maggie Lawson, Paul Greene, Christine Chatelain, Peter Benson
Duration: 1h 24mins
Genres: Comedy, Romance

Potential Northwestern fellow Tess Harper lasers through her best friend's wedding planning like the star doctor she hopes to soon become.
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A Rose for Christmas (2017)

Starring: Marc Bendavid, Rachel Boston, Venus Terzo, Willa Milner
Duration: 1h 24mins
Genres: Drama, Romance

A young woman in charge of building a float for the Rose Parade clashes with the executive whose company is sponsoring it.
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Northern Lights of Christmas (2018)

Starring: Ashley Williams, Corey Sevier, Genelle Williams, Laura Miyata
Duration: 2h 0mins
Genres: Romance

Zoey Hathaway (Williams) has been working towards her lifelong goal of being a pilot for years, but everything is thrown off-course when she unexpectedly inherits a reindeer farm, along with the dangerously handsome ranch hand Alec Wynn (Sevier).
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