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The Top 10 Movies To Watch This Valentine’s Day

Updated: Feb 10, 2022



The best medicine for dark times is a romantic comedy. If you disagree, you clearly never had a totally rotten day instantly cured by some Nora Ephron magic. When you watch a movie that includes a soundtrack with both Louis Armstrong and The Cranberries, you’ve got a recipe for happiness. These movies are engineered to be mood-boosters and often feature memorable classic lines; someone who was, at one time, referred to as “America’s Sweetheart”; and a comically memorable best friend. It's these qualities on which we can rely. Here, all the rom-coms you can watch right now to brighten your quarantine mood.



1. 10 Things I Hate About You (1999)


This is a 1990s Seattle-grunge take on Shakespeare’s The Taming of the Shrew. Julia Stiles stars as Kat Stratford, who is considered abrasive and unapproachable by her classmates. Her younger sister, Bianca (Larisa Oleynik), is a bubbly preppy type who just wants to be allowed to date, but their father (Larry Miller) won’t allow that until Kat does. New-kid Cameron (Joseph Gordon-Levitt) hires the school bad boy Patrick Verona (Heath Ledger) to take Kat out so Cameron can land Bianca as his girlfriend. This plot is full of so many twisty elements, it’s like...Shakespeare or something.



2. You’ve Got Mail (1998)



This is the movie that established that fall in New York, particularly on the Upper West Side, is magic; that all dogs named Brinkley are automatically charming; and that “Patricia makes coffee nervous.” Get a bouquet of freshly sharpened pencils and settle in to take two of Meg Ryan/Tom Hanks 1990s chemistry.



3. While You Were Sleeping (1995)


Lucy (Sandra Bullock) is a transit worker who fantasizes about Peter, a customer she sees every day (Peter Gallagher). When Peter falls and hits his head on the train tracks, Lucy saves his life. While Peter is in a coma, Lucy gets to know his family and lets them believe she's his fiancée. But Lucy's also starting to fall in love with Jack (Bill Pullman)—Peter’s brother.



4. Something’s Gotta Give (2003)


Harry Sanborn (Jack Nicholson) is an old womanizer used to his habits. While away with his girlfriend, Marin (Amanda Peet), at her mother’s Hamptons beach house, he has a heart attack and ends up moving in to recover. Of course. Marin’s mother, playwright Erica Barry (Diane Keaton), is tasked with taking care of the ornery Harry, and she ends up getting way more than she bargained for. And then we get the best crying scene in romantic-comedy history.



5. Sleepless in Seattle (1993)


Sam’s (Tom Hanks) wife has just died, and he moves with his young son Jonah (Ross Malinger) to Seattle. On Christmas Eve, Jonah calls a radio therapist to help his dad get a new wife. Soon, Sam’s got letters coming in from all over the U.S., including one from a Baltimore reporter named Annie (Meg Ryan). “You don’t want to be in love. You want to be in love in a movie,” Annie’s friend Becky (Rosie O’Donnell) tells her. And that right there, folks, is the whole premise of this wonderful film.



6. Notting Hill (1999)


William Thacker is a bookshop owner in London’s Notting Hill, where he meets movie star Anna Scott (Julia Roberts). They quickly fall in love, but as they move from affair to relationship, they have to encounter the stark differences in their lives.



7. How to Lose a Guy in 10 Days (2003)


Andie Anderson (Kate Hudson) works for a women’s magazine but wants to report hard-hitting stories. When she pitches the idea of getting a man to leave her after 10 days, her boss (Bebe Neuwirth) jumps at it. Ben Berry (Matthew McConaughey) is on a separate mission to get a woman to fall in love with him in 10 days. Obviously, this makes for great comedy.



8. When Harry Met Sally (1989)


If you watch movies for their dialogue, this one will satisfy. Harry (Billy Crystal) and Sally (Meg Ryan) first meet while driving from Chicago to New York together after college graduation in the late '70s. Over the years, they keep running into each other and eventually become friends, but Sally never forgets what Harry once told her on that drive: “Men and women can’t be friends.” This movie explores that theory and also allows Carrie Fisher to drop the classic line, “I will never want that wagon-wheel coffee table.” And once you learn that Sunday isn’t included in Sally’s “days of the week underwear” “because of God,” you won’t think of anything else.



9. Pretty Woman (1990)


Garry Marshall has a way of crafting romantic comedy that instantly becomes canon.Pretty Woman is a modern take on Cinderella; Vivian Ward (Julia Roberts) is a sex worker hired by the wealthy Edward (Richard Gere) to play the role of his girlfriend for six days. Yeah, if we start analyzing this one under a feminist lens, we’ll never stop. Anyway, this turns into a love story, and Vivian does get some killer lines along the way. “Big mistake—huge!”



10. Love Actually (2003)


It seems every actor in England is in Love Actually, which is probably the main reason people watch it even when it's not the holiday season. The movie revolves around ten separate stories that are all delightfully interwoven and which all somehow feature excellent turtlenecks. Hugh Grant, Colin Firth, Emma Thompson, Alan Rickman, and more will positively charm you.







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