As much as Valentine’s Day might be about going out with a loved one, dressing up and buying a fancy dinner, for many others, it’s also the international holiday for rom-coms. A rom-com — short for romantic comedy — is “a movie or play that deals with love in a light, humorous way,” and I can easily attest that they’re my favorite genre of movie. There’s nothing better than setting in after a long, hard day and putting on my favorite rom-com.
My favorites tend to be from the 90s to early 2000s (because somehow movies were just better back then), so this is my comprehensive list of the best rom-coms to put you in the Valentine’s Day spirit.
Starting off strong, this is probably one of my all time favorite movies. Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You features Julia Stiles as Kat Stratford. She is a puppet in her sister Bianca’s plot to get Kat a boyfriend, since their father’s rules say Bianca can’t date until Kat does. Enter Heath Ledger as Patrick Verona, the new kid who quickly becomes part of Bianca’s scheme. You literally cannot go wrong with this movie — I love it just as much everytime I watch it, and it is the perfect, not-too-cheesy, high school romance.
Starring Alicia Silverstone as Cher, Clueless is based on Emma by Jane Austen. Cher is the typical popular high school girl who thinks of herself as an expert on romance — she sets up two of her teachers, and then befriends new student Tai, turning her into a popular girl. When Tai’s popularity grows, Cher realizes that her efforts to set other people up were actually stopping her from seeing that her ex-stepbrother (Paul Rudd) was actually right for her all along. This is the perfect witty social satire poking fun at the consumerist Beverly Hills society and the rom-com genre itself. Clueless is definitely a romance and coming-of-age story, but it is also about becoming a better person, making it a fun Valentine’s Day movie.
Following the story of thirteen-year-old Jenna Rink (Jennifer Garner) who is suddenly transformed into a thirty-year-old woman after wishing for a boyfriend and imagining being an adult, 13 Going on 30 is one of the first rom-coms I remember watching and becoming obsessed with. Seeing Garner play a thirteen-year-old in a thirty-year-old’s body, showing intense emotion without holding back or trying to seem sophisticated, this movie offers the perfect combination of nostalgia for middle school years while also reminding us that we should make the most of what we have now. Jenna Rink soon realizes this herself as she discovers that adulthood isn’t as perfect as it looks, making her miss what — and whom — she had as a thirteen-year-old girl.
Starring Kate Hudson as Andie Anderson, I’m sure most people have heard of this movie by now, especially with its recent TikTok trend. How to Lose a Guy in 10 Days tells the story of Andie Anderson, an advice columnist, who decides to write a piece about how to get a man to leave a romantic relationship in ten days. Enter Ben Berry, played by Matthew McConaughey, who made a bet with his coworkers that he could get a woman to fall in love with him in 10 days. When Andie and Ben meet, their plans begin to backfire, making for one of the funniest and cutest rom-coms to date. If you’re looking for a laugh this Valentine’s Day, this is the perfect movie for you.
Culminating in a final romantic scene set on Valentine’s Day, Sleepless in Seattle is a great choice for this holiday. Tom Hanks stars as Sam Baldwin, a man who moves to Seattle with his son Jonah after the death of his wife. Jonah calls a radio talk show in efforts to find a new wife for his dad, who grudgingly gets on the line, causing reporter Annie Reed (Meg Ryan) to fall for him, despite her engagement. She sends Sam a letter asking him to meet her at the Empire State Building on Valentine’s Day. The father-son dynamic, witty dialogue and discussion of fate make this movie one of the best rom-com classics.
Harry (Billy Crystal) and Sally (Meg Ryan) shared a car ride from Chicago to New York as college graduates in 1977 and spent the whole time arguing about whether or not men and women can ever be strictly friends. They part ways intending to never see each other again, but somehow keep running into each other. They soon struggle to balance the dynamic of enemies, friends and lovers. Constantly reminding the audience that friendship is necessary for love, When Harry Met Sally is a perfect feel-good movie for Valentine’s Day.
This movie is lesser known than the others I have listed, but it is definitely worth the watch. Will Hayes, played by Ryan Reynolds, is a father in the middle of a divorce whose daughter (Abigail Breslin) asks him to tell her about how he met her mother. He decides to turn this into a game, flashing back to 1992 and telling her the stories of three different women he fell in love with, changing their names so his daughter can guess which one became her mother. This movie is so good because it is based on recognizing mature truths about love and life, and emphasizes that even if the ending isn’t the one you’d hoped for, that doesn’t mean it can’t still be happy.
I know I didn’t cover everything with this list, but these are some of the best rom-coms that I love to watch every year. Whether it’s to celebrate Valentine’s Day, or to laugh over a feel-good movie, I definitely recommend checking out these classics!
Freya Nangle is a sophomore in the College of Arts and Sciences. She can be reached at [email protected]