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10 Things I Hate About You Julia Stiles Heath Ledger
10 Things I Hate About You Julia Stiles Heath Ledger
Touchstone Pictures

Must Watch Rom-Coms for Valentine’s Day

One of my favorite genres of all time is the Rom-Com genre. Specifically, Rom-Coms from the 1980s, 90s, and early 2000s. I truly believe that there is a Rom-Com for a person of any taste: enemies to lovers, friends to lovers, will they/won’t they, fake dating, the tropes are endless. In honor of Valentine’s Day, I wanted to compile a list of the Rom-Coms I think are best suited for this holiday so that even if you don’t have a Valentine yourself, you can live vicariously through these timeless love stories.

  1. Notting Hill (1999) – This list would not be complete without a Julia Roberts Rom-Com. There are numerous to choose from, but this movie in particular has always had a special place in my heart. The story follows Julia Roberts as a famous American film actress who ends up crossing paths with Hugh Grant’s character, an awkward but charming owner of a bookstore in London. For a while she is introduced to his world, his quirky group of friends, and a life away from the cameras and lights of Hollywood. 
  2. When Harry Met Sally… (1989) – Possibly the best Rom-Com of all time, this movie is the epitome of the will they, won’t they trope. Over the course of twelve years Harry and Sally go from hating each other, to befriending each other, to loving each other, to hating each other. It’s a rollercoaster. Again, you could watch any of the Meg Ryan Rom-Com trinity (see also: You’ve Got Mail and Sleepless in Seattle) and see a great film, but this story will always be a classic. The soundtrack, the New York City setting, the sweaters, and Billy Crystal’s lines all make for a perfect Valentine’s Day watch.
  3. How to Lose a Guy in Ten Days (2003) – Admittedly, I didn’t see this film until recently, but I can see why it’s so beloved among Rom-Com watchers. Starring Matthew McConaughey and Kate Hudson, the story follows a woman who has been tasked to write a magazine article about how to lose a guy in ten days and a man who has been challenged to make a woman fall in love with him in ten days. Naturally, this complicates both of their agendas but, of course, true romance blossoms. 
  4. 10 Things I Hate About You (1999) – I feel like this movie has become somewhat of a must-watch among our generation, so naturally it needed to be on this list. I have seen this movie too many times to count, but I never get tired of it. Enemies to lovers, dare to date trope, 90s teen nostalgia, Heath Ledger, it encapsulates everything one would want from a Rom-Com. When Patrick Verona is paid to take Kat Stratford on a date the task is not easy, but after spending time with one another, tensions give way to affection.  

Granted, I likely didn’t introduce you to any completely novel movie you’ve never heard of before in this list, but if you’re considering watching a Rom-Com this Valentine’s Day I hope this selection can help to ease the decision process.

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Hannah Grinnell

Conn Coll '24

Hi! My name is Hannah and I am currently a Sophomore at Connecticut College. I am planning on majoring in Environmental Studies.
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