The Best Romantic Comedies for a Cold Winter’s Night

Chilly weather keeps you indoors and sometimes keeps your spirits down, too. Watching romantic comedies can uplift those spirits and have you ready to face the cold head-on, especially if you have someone to cuddle with — even if they’re of the dog or cat variety. Whenever you’re looking to watch free movies on a cold winter’s day, a romantic comedy is a good choice. Check out our picks for the best romantic comedies to watch on a cold winter’s night.

“500 Days of Summer” (2009)

Although not literally about the season summer — the title is a pun because the woman’s name is Summer — this romantic comedy is ideal for winter because it will warm your heart. Starring Joseph Gordon-Levitt and Zooey Deschanel, “500 Days” follows the love story of Summer and Tom. Summer agrees to date Tom, but she makes it clear she’s not looking for anything serious. Tom, meanwhile, falls in love and thinks he can change her mind.

Another reason this movie makes for a great winter film is because even with heartbreak — and there is plenty of it — there’s a message that every situation can have a happy ending. When winter gets you down, this film will remind you that warmer and happier days are ahead.

“You’ve Got Mail” (1998)

A modern remake of the classic film “The Shop Around the Corner,” “You’ve Got Mail” features Meg Ryan and Tom Hanks in one of their most popular romantic comedy pairings. Kathleen and Joe meet online, venting anonymously to one another about their problems and engaging in discussions about their favorite things, particularly books.

It turns out Kathleen runs an independent bookstore that’s on the verge of collapsing, whereas Joe’s family runs a large chain of bookstores that could put Kathleen’s store out of business. While both are currently seeing other people, they live in the same area and slowly become involved in each other’s lives offline as well as online.

“Holiday Inn” (1942)

This classic rom-com featuring Bing Crosby, Fred Astaire, Virginia Dale and Marjorie Reynolds is a must-see. Perhaps you’ve heard of “White Christmas,” another classic romantic comedy from over a decade later with Crosby; Crosby wrote the song that inspired that movie for “Holiday Inn.”

“Holiday Inn” starts with a dancing trio, Jim, Lila and Ted, who decide to break up their nightlife act after Ted leaves the company with Lila, who was dating Jim at the time. As Jim mends his broken heart with a new dancer, Linda, Ted comes back into the picture — with his eyes set on Jim’s new girlfriend. The film takes place at a supper club that’s open only for holidays. Of course, Christmas, New Year’s, Thanksgiving, Valentine’s Day and other winter holidays are important to the plot and will keep you in the seasonal mood while you watch during the cold winter months.

“The Princess Bride” (1987)

Based on the humorous novel of the same name, “The Princess Bride” is the ideal romantic comedy for the winter season because it’s the time of year when you most wish to transport yourself to a fantasy world, away from the cold and drudgery. Robin Wright and Cary Elwes star as Buttercup and Westley, the daughter of a farm owner and her farmhand who fall in love and wish to marry. When Westley leaves to make money to support his bride, he’s attacked on the open sea by the Dread Pirate Roberts and vanishes.

Years pass and Buttercup becomes a boorish prince’s fiancée, although her heart always belongs to her beloved. When Buttercup is kidnapped and meets the Dread Pirate Roberts who killed her love, her devotion to Westley is tested. There are other characters introduced along the way who make this film a zany, romantic adventure.

Check an online movie site for streaming or head to your local library and see if they have a copy you can borrow. That way you won’t have to spend a dime to see these movies that are sure to warm your heart.

Image provided by Sean Claes from Flickr’s Creative Commons


About the Author: Erica Arnold is a contributing blogger and writer who uses sites such as Crackle for her film needs. She’s also an assistant professor of film studies at a small college.

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