Best movies like Christmas Dilemma

A unique, carefully handpicked, selection of the best movies like Christmas Dilemma Starring B.J. Britt, Rafael Castillo, Christopher B. Duncan, Brittany S. Hall, and more. If you liked Christmas Dilemma then you may also like: Nothing Like the Holidays, Christmas Do-Over, Make the Yuletide Gay, The Best Man Holiday, Seasons of Love and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

Newlywed couple Jay and Monica struggle to decide which set of in-laws they should join for their first Christmas. They eventually decide against picking one family over the other. Little do they know, their decision is made for them when their families show up unannounced.

selected filters: Sort: Default

You may filter the list of movies on this page for a more refined, personalized selection of movies.

Still not sure what to watch click the recommend buttun below to get a movie recommendation selected from all the movies on this list

Know any good movies to watch like Christmas Dilemma 2020. With a similar plot or stoyline. Suggest it.

Nothing Like the Holidays

It’s Christmastime and the far-flung members of the Rodriguez family are converging at their parents’ home in Chicago to celebrate the season and rejoice in their youngest brother’s safe return from combat overseas.

Christmas Do-Over

A ne'er do well father and ex-husband who always raced his way through the holidays is forced to relive Christmas Day time and again until he gets it right in this family oriented fantasy comedy starring Jay Mohr. It's Christmas time once again, and as usual Kevin (Moore) is scrambling to get his son Ben a last minute gift before stopping by his ex-wife Jill's house for a quick swig of eggnog. Ben can't stand Jill's impossibly perfect new boyfriend, and the prospect of spending the entire evening with his former inlaws is nearly too painful to ponder. But this Christmas things are going to be different, because this Christmas might just last forever. At first Kevin resists the curious development by simply reverting to his childish ways, though he is about to find out that sometimes in order to build a better future one must finally make amends with the past. ~ Jason Buchanan

Make the Yuletide Gay

The holidays get overly festive as Olaf "Gunn" Gunnunderson, an out-and-proud gay college student, crawls back into the closet to survive the holidays with his parents. But when his boyfriend, Nathan, shows up at their doorstep unannounced, Gunn must put on a charade to keep the relationship a secret. With pressure mounting from all sides, will Gunn come out before the truth does?

The Best Man Holiday

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

Seasons of Love

Set in the picturesque backdrop of New York, "Seasons of Love" is a romantic, soulful holiday drama about two people who struggle to find love against the odds, while reconciling with the past and learning the true value of family.

My Dad's Christmas Date

It’s Christmas and the charming city of York, home to Jules, 16 and her Dad, David is decked out ready for the festive season. In many ways, David and Jules’ relationship is no different from that of most fathers and their sixteen-year-old daughters. He struggles to understand her, she refuses to communicate with him. He wants to be involved in her life, she wants her own space. In one important respect, however, David and Jules share a profound bond: the death of Jules’ mum, and David’s wife, in a car crash two years before. With both struggling to cope with everyday life in the shadow of their loss, Jules, inspired by happy memories of her mum, decides to take matters into her own hands.

The Christmas Box

A ski-shop owner reluctantly moves himself, his wife, and his daughter in to an estate as live-in help for an elderly widow. While struggling to balance his career and family life, he has recurring dreams about an angel.

Gift of the Magi

A newlywed couple burdened with economic hardship decides not to exchange Christmas presents to save money over the holidays. Secretly, they make sacrifices to buy the other a special gift.

Operation Christmas

As her new romance blossoms, a single mother, Olivia, is dismayed when her boyfriend, Scott, a military sergeant, is deployed right before Christmas. Determined to not let it ruin the holidays for her and her children they decide to give back to the struggling military families on his base and, as their efforts go viral, they are rewarded in ways they never imagined.

Entertaining Christmas

Candace, daughter of lifestyle mogul Liz Livingstone, has never lived up to her mother’s standards. When a young girl posts a video begging Liz to help arrange a special Christmas party, Candace is sent in her place. As she struggles to prove herself worthy of running the company, Candace meets—and begins falling for—the girl’s uncle, a reporter writing an expose on her.

The Christmas House

Working through some difficult decisions, Mitchell family matriarch Phylis and patriarch Bill, have summoned their two grown sons – TV stars Mike Mitchell and Brandon Mitchell – home for the holidays. It is their hope that bringing the family together to recreate the Christmas house, will help them find resolution and make a memorable holiday for the entire family and community.

Christmas on the Bayou

When successful New York marketing executive Katherine discovers her workaholic ways are taking a toll on her eight-year-old son, Zac, she decides to spend Christmas with him and her mother, Lilly in her home town on the bayou. When Caleb tries to rekindle a childhood romance and convince her to move back home, Katherine is torn between the bright lights of the big city and the quiet, gentler rhythms of her Southern roots. Only a Christmas miracle orchestrated by Papa Noel can steer her heart to her true home.

Christmas Around the Corner

Claire (Alexandra Breckenridge), a savvy venture capitalist from New York City, escapes to a quaint town in Vermont for the holidays and becomes a guest of the Fortenbury Bookstore. Upon arrival, Claire finds Christmas celebrations have been canceled by the town after a flood and the bookstore is in a dire state of disrepair. She immediately takes on the challenge to revitalize the store, but clashes with the owner, Andrew (Jamie Spilchuk), who initially rejects all her proposed improvements. Eventually, sparks fly as the two begin a budding romance, and Claire’s infectious optimism inspires Andrew to join her in reviving the yuletide spirit. But everything comes to a screeching halt when Claire discovers that Andrew is planning to sell the bookstore in the New Year. Will the spirit of Christmas be enough to change Andrew’s mind and encourage him to follow his heart?

Once Upon A Holiday

When an actual, honest-to-goodness royal princess runs off from her official obligations and duties for a couple of days to see how the other half lives, she winds up falling for a good Samaritan who is unaware of her real identity during the holiday season. Will her true love still feel the same way once he learns the truth?

Hometown Holiday

Krista is starting this New Year with a new business and a resolution to be more selective with who she dates. When Krista meets Ryan Rourke, an entertainment lawyer from LA, the two really hit it off. Ryan is in her hometown to sign a local rancher turned viral signing sensation as his new client. Now with Krista also in Rust Creek, maybe there is more of a reason to stick around. Both are holding onto things from their past and are forced to make some decisions if they truly want to be together.

The Christmas Calendar

When Emily, a struggling baker in a small town, receives a handmade Christmas Calendar from a secret admirer, the local residents become obsessed with finding out the identity of the sender.

A Christmas Arrangement

Flower shop owner Poppy enters the annual holiday floral show for a chance to win the grand prize but standing in her way of victory is Garrett, the underappreciated protégé of florist extraordinaire, Blair. While Poppy and Garrett’s rivalry heats up on the flower show floor, an undeniable romance begins amidst a whimsical holiday backdrop.

Christmas in Wolf Creek

A woman and her new boyfriend are struggling to maintain their relationship. However, when a runaway reindeer threatens the annual Christmas play, the couple must work together to save Christmas for the town and each other.

A Family Thanksgiving

A happily single, self-absorbed, workaholic corporate lawyer is living the high life in New York City until she awakes in alternative reality. Now a wife and stay-at-home mom, Claudia struggles to make sense of her new life.

A Christmas Cruise

When her best friend invites her along for a holiday themed sail, an aspiring novelist, Pam, unexpectedly finds the love of her life on board. But what will happen when the ship returns to port for Christmas?

Merry Liddle Christmas

The messy family of a successful, super-together single tech entrepreneur descends on her gleaming new dream home for the holidays. Christmas traditions collide and family drama ensues as she struggles to keep her house together in time for a glossy video shoot of "the perfect Christmas."

A Christmas Wedding Tail

It's love at first sight when Rusty the Labrador and Cheri the Poodle meet one day while jogging in the park. Even better- their owners fall in love too! But love is more complicated for the people, Susan and Jake, who marry and attempt to join together their large family of five children. With kids fighting and a household in complete chaos, it's up to the dogs to keep the family together.

Baking Christmas

When their mother decides to retire, her three children organize Christmas Cake Off to choose which one of them is going to take over the family bakery.

A Sugar & Spice Holiday

The film follows Chinese American Suzie who draws on her family’s cultural traditions to spice up an old-fashioned Christmas baking competition. Suzie, a rising young architect, returns to her small hometown in Maine for Christmas where her Chinese American family runs the local Lobster Bar. Following the loss of her beloved grandmother who was a renowned baker in their community, Suzie is guilted into following in her grandmother’s footsteps bei entering the local gingerbread house competition. Teaming up with an old high school friend Billy, who grew up to be catch, Suzie must find the right recipes and mix of sugar and spice to win the competition and perhaps find some love in the process.

Christmas Belles

Despite being successful in their careers, two 30-something BFFs never stop hearing that they both need a man before it's too late. When a handsome pastor arrives just in time to kick off the Christmas season, both ladies try to make a move-but as their hilarious attempts to one up each other keep growing, it will be up to their family to remind them what the holiday season is truly about.

Recipe for a Perfect Christmas

The holiday season is turned upside down for a neophyte food critic JJ (Pope) when her uninhibited mother (Baranski) shows up unannounced. In an attempt to occupy her mom's time, JJ works out a deal with a young chef (Cannavale) that stirs up some matters of the heart.

The App That Stole Christmas

A tech entrepreneur's Christmas shopping app is a smashing success, but he starts to realize his invention might be ruining the holiday spirit.

Good Morning Christmas!

Two competing TV hosts are sent to a festive small town over Christmas. While pretending to get along for the sake of appearances, they discover that there’s more to each other than they thought.

Reunited at Christmas

Frazzled and struggling with writer’s block, novelist Samantha, along with her boyfriend, heads home to her late grandmother’s home to spend Christmas. While at home with family, her grandmother’s wise words reveal the true meaning of Christmas with Samantha at a time when she most needs encouragement.

A Christmas Duet

Former couple and pop music duo Averie and Jesse unexpectedly reunite at her inn during the holidays. As they spend time together, they rediscover long-buried feelings and must decide if they are meant to live their lives solo or in harmony together.

Angel Falls: A Novel Holiday

Hannah is a book editor and she must work with her former rival Ryan to help a potential writer find her way. However, life seems to have other plans for Hannah as Angel Anthony reminds the duo about the miracle of Christmas and the value of community.

Christmas at Graceland: Home for the Holidays

World-traveler Harper returns to Memphis and meets wealthy widower Owen who hires her to au pair for the holidays. As they prepare for a joint event at Graceland, their feelings grow for each other. Harper realizes she enjoys living near family and must decide if Memphis will be her forever home.

Middleton Christmas

In a small town, high-school dean Alana and her vivacious teenage daughter Samantha plan a holiday concert to save the school with the help of the new maintenance man, Army veteran Johnny, and his quiet son Max. But when a car accident lands Sam in a life-threatening condition, Alana turns to Johnny for support, and Max makes a desperate decision that will forever bond their families together. All four must question their values about sacrifice, family, and love - and what it means to be thankful for another Christmas.

Christmas at Grand Valley

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 time this holiday season. When he is assigned to review a hotel in Grand Valley for its value, he sees this as the perfect opportunity for a Christmas family vacation. It isn’t long until Kelly and Leo’s worlds collide.

Sweet Navidad

A pastry chef dreams of opening her own dessert shop; she is paired with another chef for a grand event during which they must learn from one another and eventually come together to create a menu in time for Christmas.

More custom members lists

Sort results by:

X close
Default
Clear filters
...