Movies Similar to How to Marry a Billionaire: A Christmas Tale

The Apartment(1960)

Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.

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About a Boy(2002)

Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.

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Willy Wonka & the Chocolate Factory(1971)

When eccentric candy man Willy Wonka promises a lifetime supply of sweets and a tour of his chocolate factory to five lucky kids, penniless Charlie Bucket seeks the golden ticket that will make him a winner.

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Brazil(1985)

Low-level bureaucrat Sam Lowry escapes the monotony of his day-to-day life through a recurring daydream of himself as a virtuous hero saving a beautiful damsel. Investigating a case that led to the wrongful arrest and eventual death of an innocent man instead of wanted terrorist Harry Tuttle, he meets the woman from his daydream, and in trying to help her gets caught in a web of mistaken identities, mindless bureaucracy and lies.

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The Santa Clause 2(2002)

Better watch out! The big guy in red is coming to town once again. This time, Scott Calvin -- also known as Santa Claus -- finds out there's an obscure clause in his contract requiring him to take on a wife. He has to leave the North Pole to fulfill his obligations, or else he'll be forced to give up his Yuletide gig.

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Christmas Plus One(2022)

When sisters Cara and Amy make a pact to find their soulmates by next Christmas, they’re not expecting to be so successful! One year later, Amy’s winter wedding approaches and Cara finally finds her own perfect man, inviting him as her plus one. But after immediately losing his number, all hope is lost. Will she find him in time to make her Christmas wish come true? Or does love have other plans for Cara?

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Hello Ghost!(2023)

After a failed attempt to take his own life, a man discovers he's returned with four ghosts seeking to fulfil their last wishes in hopes of earning his own place in the afterlife.

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How the Grinch Stole Christmas(2000)

The Grinch decides to rob Whoville of Christmas - but a dash of kindness from little Cindy Lou Who and her family may be enough to melt his heart...

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Go(1999)

A supermarket clerk decides to step in for an absent drug dealer, setting off an explosive, comedic chain of events.

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Coupled Up for Christmas(2023)

This was supposed to be the Christmas Tiffany finally gets reunited with her long-time crush Brett– but when she finds out he has a serious girlfriend, who is just perfect, she is devastated. Tiffany hatches a plan with a recently heartbroken Peter, to win back the affection of their respective soulmates by pretending to be a couple in love, but soon realise that they have more in common than they ever realised… Tiffany might just find love this Christmas after all.

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You've Got Mail(1998)

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.

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You're Everything To Me(2016)

When an old fling shows up with their infant child, a dallying man-child must take on the role of father and create a fairytale world for his daughter.

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Single All the Way(2021)

Desperate to avoid his family’s judgment about his perpetual single status, Peter convinces his best friend Nick to join him for the holidays and pretend that they’re now in a relationship. But when Peter’s mother sets him up on a blind date with her handsome trainer James, the plan goes awry.

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The Road Home for Christmas(2019)

Two rival musicians, Lindsay and Wes who perform in a dueling piano show, suddenly find themselves without a gig on Christmas Eve and decide to road trip to their neighboring hometowns together.

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Radio Christmas(2019)

When her Philadelphia radio station is closed for repairs during the holidays, DJ Kara Porter is forced to broadcast from the small town of Bethlehem.

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A Very Vintage Christmas(2019)

Dodie is a hopeless romantic just like the pieces in her vintage antique shop. When Dodie finds a hidden box full of romantic trinkets, she makes it her mission to deliver it to its rightful owner. Following the address, she manages to persuade the handsome but reluctant new tenant, Edward, to help her with her search.

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A Christmas Wish(2019)

Every December in the small town of Ponchatoula, Louisiana a wooden wishing box is placed in the park as a Christmas tradition. After a night out together, Maddie encourages her sister Faith to put a wish in the box - a wish to experience true love for the first time. Faith and Maddie are surprised the next day when she meets the very handsome and eligible Andrew. As Christmas nears, Faith begins to wonder if Andrew is really perfect for her, or if the wish is leading her to her best friend, Wyatt.

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Christmas a la Mode(2019)

The dairy farm Emily has been running since her father passed away has fallen on hard times. When Emily’s sister, Dorothy, and her handsome business partner, Charlie, show up with a proposition to sell the farm, Emily comes up with an ingenious plan to buy out her sister's shares. She holds an online holiday ice cream flavor contest that goes viral with the help of a key ingredient, Charlie's amazing apple pie. Still, as the Christmas Eve deadline for the buyout approaches, Emily needs a Christmas miracle to save the family farm and her father's legacy.

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Random Acts of Christmas(2019)

While uncovering who is behind the random acts of Christmas popping up around her city, investigative journalist Sydney meets a competing reporter, Cole, who ignites her Christmas spirit and captures her heart, but may not be the man he claims to be.

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Matchmaker Christmas(2019)

As the Christmas party for a book publishing company approaches, editor Maggie volunteers to help her boss Amanda find a date. Matchmaking is a bit of a hobby for Maggie, but she is thrown off her game when Jaxson, her old boyfriend from her college years, shows up at her work — as a newly signed, successful author. Maggie would love to deny she feels anything for him still, but Jaxson isn’t making it easy. She’ll have to face her decisions of the past, along with Amanda eyeing Jaxson, to bring together the perfect matches at Christmas.

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