10 Love-Filled Holiday Movies to Watch During Your Stay-at-Home Christmas

As part of our “Love Essentially” series, Jackie Pilossoph helps us navigate the complex world of relationships. Have a question that you would like her to answer? Contact her here, and it may be featured in an upcoming ar

It’s beginning to look a lot like Christmas, and yet it isn’t. Looking at all the beautiful holiday lights and decorations on the North Shore, you’d never know that the CDC is recommending small or no gatherings over the Christmas holiday weekend.

But staying home over the holidays doesn’t have to mean feeling sad and depressed, especially if like me, you’re a movie lover. Several years ago, when I was first getting divorced, I spent four days alone during Christmas, while my kids were spending the holiday with Dad. Thank goodness for the delightful, cute, funny and romantic Christmas movies I watched to fill time and to cope with my loneliness. 

I must have watched a dozen movies that week and before I knew it, my kids were back home and the holidays were over. What stuck with me, however, were the funny lines, the memorable scenes, the cute actors, the hopeful messages and the happy endings the movies provided me and still do.  

If you are looking for some great holiday flicks to watch alone or with your spouse, a friend or the whole family, here is a list of my 10 favorite holiday movies. 

Serendipity (2001)

While Christmas shopping in New York City, a couple (played by John Cusack and Kate Beckinsale) who are both in relationships find a connection. They decide to say goodbye and let fate determine if they are meant to meet again. Which they do, of course! 

The Family Stone (2005)

One cast member is more loveable than the next in this Christmas dramedy. Sarah Jessica Parker, Diane Keaton, Claire Danes, and the adorable, Luke Wilson spend the holidays at the Stone’s, where relationships are being tested, some newcomers are being unfairly judged, and unexpected romance is running rampant. 

Four Christmases (2008)

In another star-filled comedy, a couple (played by Vince Vaughn and Reese Witherspoon) decide to spend Christmas day visiting each of their parent’s homes—four in total. Each gathering is silly, hilarious, and heartwarming, and collectively they lead the couple to look in the mirror and ask how much they really know about each other. After watching this, you’ll be thankful for the family you have, regardless of their flaws!

The Preacher’s Wife (1996)

An angel (played by Denzel Washington) comes down from heaven to help a preacher and his wife (played by Whitney Houston) get their church and their marriage back on track. With a soundtrack of songs by Houston, this movie is uplifting and adorable.  

The Holiday (2006)

To soothe their broken hearts, a Hollywood film-trailer maker (played by Cameron Diaz) and a small-town newspaper columnist based in London (played by Kate Winslet) swap houses for the holidays. Both find unexpected love. Are you really surprised?!

Elf (2003) 

An Elf living at the North Pole (played by Will Ferrell) finds out right before Christmas that he was adopted and is actually a human, so he heads to New York City to find his real father (played by James Caan.) Not only does he find his father and bring out the best in the man, but he also falls in love.

Miracle on 34th Street (1947)

I can’t imagine there were very many divorced moms in the 1940s, but this cute Christmas movie’s main character (played by Maureen O’Hara) is just that. Cynical and not looking for love, Santa shows up in her life, causing her and her also cynical daughter (played by Natalie Wood) to realize that having faith can lead to happiness, love and of course, miracles.  

Love Actually (2003)

This delightful romantic comedy follows the love lives of eight people in London during Christmastime. Each unique story, which includes The Prime Minister (played by Hugh Grant) brings humor, excitement and hope when it comes to falling and staying in love.

Trading Places (1983)

Old-money millionaire brothers make a bet that involves switching the lives of a street-smart con artist (played by Eddie Murphy) and their snobby employee (played by Dan Aykroyd) during the Christmas season. What they don’t plan on is the two becoming friends and working together to get rich. There is a little love story in this movie, too!

It’s a Wonderful Life (1946) 

I’ve saved the best for last. This classic film tells the story of George Bailey (played by James Stewart), a family man and business owner who finds himself frustrated and bitter on Christmas Eve. To help George see what life would be like had he never been born, an angel comes down from heaven and takes him on a journey that makes him realize he’s the luckiest man on earth.

I hope these movies provide you with an hour and a half of enjoyment that includes laughing, crying (in a good way), and the feelings of love, warmth and optimism. And if these aren’t enough, here’s a list for more

Happy holidays to all of you. All my best for a safe and joyous celebration that includes lots of love and romance, of course!

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Jackie Pilossoph is a former television journalist and newspaper features reporter. The author of four novels and the writer of her weekly relationship column, Love Essentially, Pilossoph is also the creator of the divorce support website, Divorced Girl Smiling. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers.

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