Cozy up for Christmas with these romantic holiday movies

The holiday season is upon us, and with it comes the familiar tradition of cozying up with a cup of cocoa, coffee — or a glass of wine — and indulging in holiday movies. For many, these films — especially the romantic ones — are the perfect way to get into the festive spirit. But if you’re flying solo this season, you might wonder: How can a love story make you feel warm and fuzzy when you’re not in a relationship? Surprisingly, romantic holiday movies have a unique ability to give you all the "feels," whether you're single, taken, or somewhere in between. Here are some of my favorites:

Sleepless in Seattle (1993)

Starring: Meg Ryan, Tom Hanks, Rosie O’Donnell, Ross Malinger, Bill Pullman

After the death of his wife, Sam Baldwin (Hanks) moves to Seattle with his son, Jonah (Malinger). When Jonah calls into a talk-radio program to find a new wife for his father, Sam reluctantly gets on the line to discuss his feelings. Annie Reed (Ryan), a reporter in Baltimore, hears Sam speak and falls for him, even though she is engaged. Unsure where it will lead, she writes Sam a letter asking him to meet her at the Empire State Building on Valentine's Day.

Editor’s note: Some may argue that this isn’t technically a Christmas movie, but it has Christmas and New Year’s elements. Christmas was the catalyst for the movie: it was on Christmas Eve that Annie discussed destiny with her mother, making her question if she’s marrying the right man. It was also on Christmas Eve that Annie heard Sam on the radio talking with Dr. Marcia Fieldstone, the radio psychologist.

While You Were Sleeping (1995)

Starring: Sandra Bullock, Bill Pullman, Peter Gallagher

The story follows Lucy (Bullock), a lonely fare token collector who secretly admires a commuter named Peter (Gallagher). Peter falls into a coma after an accident, and Lucy saves him. His family mistakes her for his fiancée. As Lucy becomes close to Peter’s family, she starts developing feelings for his brother, Jack (Pullman). The film is a charming mix of humor, heart, romance, and family, showing that love and connection can come from the most unexpected places.

Editor’s note: A favorite scene in the movie is when Jack tries to walk Lucy home but they keep sliding on the slippery ice. When they finally stand up and look into each other’s eyes? Ugh. Kilig!

The Holiday (2006)

Starring: Cameron Diaz, Kate Winslet, Jude Law, Jack Black, Rufus Sewell

The movie centers on Iris (Winslet) and Amanda (Diaz) and their holiday (mis)adventures. Iris is still in love with her ex, Jasper, while Amanda is depressed after learning that her boyfriend is cheating on her. They agree to swap homes for a much-needed break. Iris ends up in a palatial Hollywood mansion while Amanda takes refuge in a picturesque English village. Both women find unexpected romance: Iris meets film composer Miles, and Amanda has a whirlwind affair with Graham, a widower and father of two.

Editor’s note: While Jude Law’s character, Graham, is attractive and a walking green flag, my heart goes to Jack Black’s Miles. He’s the ultimate adorkable. In a scene where he’s listening to his ex-girlfriend apologize for cheating on him, he plays the song “Iris” mid-air. "Iris, if you were a melody..." Ugh. Kilig. Again. Also, ladies, always remember to be the leading lady of your life and to have gumption.

Meet Me in St. Louis (1944)

Starring: Judy Garland, Tom Drake, Margaret O’Brien

A classic MGM musical comedy. It’s 1903, and Esther (Garland) is in love with her neighbor John Truett (Drake). She’s been trying to express her feelings to him, but when her father announces the family’s move to New York, Esther is devastated. On the family’s last night in St. Louis, Tootie (O’Brien) is crying over the snowmen they made earlier. Esther comforts her younger sister by singing Have Yourself a Merry Little Christmas, one of the classic holiday anthems.

Editor’s note: I grew up watching this movie, which already holds a special place in my heart. Modern sensibilities might make you cringe at the teenage characters already talking about marriage, but keep in mind this movie is set in the early 1900s, when things were quite different.

An Affair to Remember (1957)

Starring: Cary Grant, Deborah Kerr

Nickie Ferrante (Grant) returns to New York to marry a rich heiress but meets nightclub singer Terry McKay (Kerr). Initially, they both think little of each other, but over several days, they fall deeply in love. They agree to meet again six months later atop the Empire State Building, giving them time to resolve their current relationships. But fate intervenes, resulting in misunderstanding and heartbreak. Only fate can save their relationship.

Editor’s note: There are numerous references to this film in Sleepless in Seattle, and both movies feature a romantic meeting atop the Empire State Building. The original soundtracks An Affair to Remember and Tomorrowland live rent-free in my head. If you haven’t seen this yet (how could you not?), watch it with a big box of tissues.

Serendipity (2001)

Starring: Kate Beckinsale, John Cusack

Jonathan (Cusack) and Sara (Beckinsale) meet during the holidays while shopping in busy New York City and hit it off. Though both are already in relationships, they feel an undeniable connection. They decide to test fate by splitting up and seeing if destiny will bring them back together. Ten years later, despite living separate lives, they still can’t forget that magical night. Will fate reunite them, or not?

Editor’s note: When this film was released, I remember it having a chokehold on women, with many dreaming of going to New York and visiting the iconic Serendipity 3 cafe for a frozen hot chocolate. The cafe was not named after the movie, though — it was chosen as a filming location.

You’ve Got Mail (1998)

Starring: Meg Ryan, Tom Hanks

Another Nora Ephron classic. Technically, this isn’t a Christmas movie, but it has Christmas elements. In the early days of the internet, bookstore owner Kathleen Kelly (Ryan) meets bookstore magnate Joe Fox (Hanks) in a chatroom. They exchange emails, though in the real world, they are business rivals. After discovering that his online penpal is his professional nemesis, Joe decides to pursue Kathleen, starting as friends.

Editor’s note: When Kathleen and her beau Frank Navasky (Greg Kinnear) amicably separate, Kathleen says one of the most memorable lines for hopeless romantics: “There is the dream of someone else.” Sigh.

Romantic holiday movies are more than just feel-good entertainment; they have a way of tugging at your heartstrings, whether you’re single, in a relationship, or somewhere in between. These films remind us that love can be found in unexpected places, and that even in moments of longing, there’s warmth and magic to be found in the connections we make with others. So grab your favorite holiday beverage, curl up on the couch, and enjoy the feels that these timeless romantic movies bring — they’re the perfect way to get into the holiday spirit!