5 Classic Rom-Coms to Watch this Holiday Season!

By: Sanaa Alam ‘25

One of the best parts of the winter holidays is cuddling next to the fireplace with a warm cup of hot chocolate or cider, spending time with family and friends, and watching holiday movies! As an avid rom-com watcher, here’s my favorite 90s and early 2000s movies perfect for embracing the holiday vibes this winter season! 

5. Serendipity (2001)

From the movie title alone, you can tell that this movie centers around themes of love and destiny. Two people, played by Kate Beckinsale and John Cusack had an encounter 10 years prior that left them pining for each other. Though they lost touch and found different partners, part of them couldn’t let go of the encounter from a decade ago. As the love between partners evolves, viewers can laugh and cry as they experience the ups and downs of this slow-burn romance.

4. Sleepless in Seattle (1993)

Starring Med Ryan and Tom Hanks, this movie keeps viewers at the edge of their seat as they await a possible encounter between the two main characters. The son of Tom Hank’s character makes a phone call to the local radio station, explaining how much his father loved his late mother. As the child describes the intensity of love Tom Hank’s character is willing to give, Tom Hanks takes on the moniker “Sleepless in Seattle.” As a result, many women across the United States contact him in hopes of landing a date. One woman tries her luck in an unconventional way, even though she is engaged to another man. As Tom Hanks’ character reads this surprising message, fate leads him to follow the mysterious message. This movie embraces the wintertime spirit of sharing love and spending time with those you love. 

3. While you Were Sleeping (1995)

Every winter, I rewatch this movie because the chemistry shared between the two main characters is truly unmatched! As Sandra Bullock, a train station manager, helps a handsome man, Peter Gallagher, escape death by oncoming train, she takes him to the hospital where the doctors say that he is in a medical coma. When his family comes to visit him, one out-of-context comment makes them believe that Sandra Bullock’s character is his fiancé. As his family decides to get to know her, she finds herself falling for someone else instead of her fake fiancée. This movie is full of shifts in the narrative and satirical moments that allow for an enjoyable movie night. 

2. When Harry Met Sally (1989)

If you’re a fan of slow-burn romances, this famous movie is definitely for you! Billy Crystal and Meg Ryan’s characters meet in college and become friends after a road trip from Chicago to New York. This drive includes a riveting argument about whether or not men and women can be platonic friends. Years later, they meet through mutual friends and see different sides of this original argument as they become closer friends.

1. Bridget Jones’ Diary (2001)

Based on a book of the same name, this movie focuses on the life of Bridget, played by Renée Zellweger, as she recounts her adventures. Even though she wants a clean slate, she reaches a crossroads in her life through her provocative, hilarious interactions with two men, Hugh Grant and Colin Firth. While this movie does not solely take place in the winter, it’s a great movie to spend time laughing with friends and family during the holiday break!

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