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Best Rom-Coms for a Chilly Night In

Emily Cackett · November 10, 2025

There is simply nothing better than getting cozy with a good movie as the days become shorter and colder. There are definitely times of year when certain movies are a better fit, and these films capture the changing seasons, romance, and humor like no other. As the temperature drops, these worthwhile films make for the ideal movie night.

  • “The Holiday”

A great movie that perfectly portrays the simplicity of winter. The film is a rom-com about two women who swap their homes for the holidays to “escape reality”. It screams to be watched with your favorite warm drink because films use snow, crackling fireplaces, and Christmas lights. Like the rest of these movies, this is the ideal comfort watch when you need to relax during the hectic winter months.

  • “When Harry met Sally”

The ultimate classic rom-com. It has the ideal fall vibe with the vibrant leaves, warm sweaters, and coffee shop conversations. It shows two friends who, over many years, end up growing to fall in love. It’s comical and cozy, and also so timeless. It’s like taking a nostalgic stroll through New York City in the fall. 

  • “Notting Hill”

This is a good choice if you are in search of a rom-com that’s charming with a gentle, rainy-day vibe. A place with cozy, comfortable lighting and peaceful streets. It’s like seeing life unfold gently in a comfortable part of London. Hugh Grant and Julia Roberts have this awkward chemistry that is so worth the wait. This movie just flows and makes it so easy to watch when you need to slow down.

  • “You’ve Got Mail”

This came out well before the takeover of online dating. Tom Hanks and Meg Ryan are two business rivals who, somehow, through anonymous emails they fall in love without even realizing it. The film has the charm of New York in the fall and has a great sense of nostalgia for the late 1990s, from the music to the old bookstores. Watching it now reminds people that love notes used to be sent through email.

  • “Love Actually”

This is a classic to add to your list to watch as the days get colder. Love Actually depicts the unpredictable but magical spirit of love during the holidays. It’s shown through the lives of eight somewhat connected couples navigating their very different love lives, the month before Christmas in London. Its bittersweet love stories inspire faith in love despite all its flaws.

  • “Serendipity”

One of the best films to watch, real trust in fate or destiny, is “Serendipity.” Where Kate Beckinsale and John Cusack meet in New York City. Even years later, they wait for fate to bring them together once again. They know in their hearts that they are “write person, wrong time”. The vibe of this film could put a smile on your face like no other because of the holiday snow and magical energy.

  • “Your Place or Mine”

This rom-com is more recent and is very much worth watching. Reese Witherspoon and Ashton Kutcher play best friends who switch their homes for a week. They become aware that what they feel may go beyond their friendship as they get used to each other’s lives. It has a charm, it has quirkiness, but mostly it was the kind of rom-com we haven’t seen come out of Hollywood in a while, that ended up feeling like it was from the early 2000s.

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