Bold Boss Mom

A Millennial Parenting Journey

5 Heart-Felt Holiday Movies Featuring Single Moms

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It’s that time of year again. And no, I’m not talking about buying, wrapping, giving, or even receiving presents. Instead, I’m talking about something a lot less stress-inducing. 

Let’s discuss the holiday movies we live for during this time. You know, the ones where love is in the air, especially during Christmas. To keep things on brand, I’ve picked out some relatable flicks.

As cheesy as some holiday movies seem, they still offer a sense of happiness to end the year.

So let’s start, or maybe end, our holiday festivities with these five heartfelt movies featuring single moms. 

The Perfect Holiday

This 2007 movie is about Nancy, a divorced single mom of three who wants to find a “nice, normal man.” Of course, because it is Christmas time, her kids and Santa are helping her make this happen.

To start, Nancy takes her kids to the mall to meet Santa. There, her daughter shares with Santa her mom’s wish to meet a nice man. 

After that, her mom meets a man named Benjamin at her store. He is a good-looking man who describes himself as a salesman. They seem to be a holiday match made in heaven. 

However, Nancy’s sons and ex-husband make her blooming relationship complicated. Also, there is a twist to Benjamin’s story.

But, just like most holiday romcoms, this one has a positive ending. You’ll want to add it to your watchlist.

The Most Wonderful Time of the Year

The Most Wonderful Time of Year follows single mom Jen and her stressful experience with Christmas. Jen approaches Christmas like a business. Her attitude and behavior have made her son lose his Christmas spirit. 

When Jen’s uncle comes to town, he brings a handsome stranger named Morgan. He literally met this man on a plane they were both on. During their meeting, Morgan describes himself as a chef and says he is in town for the holidays but without a place to stay. Jen’s uncle thought it would be a great idea to offer up her home to this stranger. Jen reluctantly agrees, which is understandable, but this is a holiday movie after all. Unlikely things happen all the time.

This movie does have some light drama like:

  • Jen’s rich boyfriend being unaware of handsome Morgan staying on her couch 
  • Morgan getting along with Jen’s son and brightening up his Christmas spirits more than his mom
  • Jen pretending she isn’t feeling Morgan and creating unnecessary tension

Regardless of the seemingly complicated storyline, this is another holiday movie treat you’ll enjoy.

The Christmas Secret

The Christmas Secret is a 2014 movie about Christine, a single mom of two, who feels her life is falling apart. On her way to work, she sees a woman collapse in front of her. She stops to give the woman CPR and saves her life.

Even though Christine did the right thing, she is late to work and fired. Adding more stress, her landlord is threatening to evict her, and her ex-husband is fighting for custody of their kids. 

On top of that triple whammy, Christine realizes she lost a valuable necklace trying to save the woman. 

Thankfully, she finds a new job and meets a man who brings good vibes to her life.

This Hallmark movie starts slow but comes together in the end. You will want to include A Christmas Secret to your movie night.

A Christmas Miracle

In this 2019 Hallmark movie, single mom Emma has her idea for a magazine cover story stolen by her boss. So Emma seeks help from her son and a close friend. But not just any co-worker, a handsome staff photographer named Marcus. 

While searching for ideas, Emma finds a way to bring a Christmas miracle to someone special she meets. But, her mission does come with some unexpected twists and turns along the way. I won’t spoil anything because I want you to see what happens on your own.

A Christmas Miracle is another Hallmark movie to watch during the holiday season.

Our Christmas Journey

In this 2021 movie, single mom, Lena, and her son, Marcus, make a tough decision around Christmas time. Lena has been homeschooling Marcus for most of his life because of his autism. Now they are thinking about mainstreaming, and of course any decision dealing with school and kids isn’t easy to make.

This Hallmark movie is not your typical Christmas love story. Instead it follows the challenges of a mom-son relationship where letting go is as complicated as it gets. 

Even though Christmas isn’t the main topic, this movie is still one to add to your holiday movie watch list.

In Closing

For my household, watching holiday movies is somewhat of a long-standing tradition. The most popular are family and kid-friendly stories. I usually enjoy romantic comedies and family dramas the most. Can’t you tell by my list?

I hope these heartfelt holiday movies featuring single moms bring a joyous end to your year. Also, share some of your favorite holiday movies, whether they feature single moms or not.

Happy Holidays!

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