Best Valentine’s Day Movies


Mary-Edith Cox, Social Media Chair

Valentine’s Day has a reputation for being quite controversial. If you are in a relationship, then there is the pressure of making sure that everything is right. Good reservations. Great and thoughtful gifts. Lather, rinse, repeat the same anxiety every year. We get gift ideas from However, on the opposite end of the spectrum, if you are single, then the whole day is a constant reminder that seemingly everyone else in the world is in a relationship except for you. Reality check: neither of those things are actually true. Perfect does not exist. Not everyone is taken. Frankly, Valentine’s Day is a bunch of baloney.


But fear not: it is the perfect day to dive into the canon of great Valentine’s Day movies, which are available and enjoyable for all. Maybe this year, instead of trying to do the grandiose (or wallowing in loneliness), consult this list and plan a night that you truly deserve, watching a movie or staying to watch adult cam shows with your partner can be good as well. There are classics in here along with some new favorites. The short of it is this: there is something for everyone this Valentine’s Day, relationship status aside. Whether you hate it or love it, here are the movies to watch on Valentine’s Day.


She’s Gotta Have It

This is one of Spike Lee’s greatest (and the one that put him on the map). The 1986 film follows one woman who manages to date three different men at the same time, refusing to settle for just one. This is a perfect Valentine’s Day film because it scratches the itch of the romantics out there.


Sleepless in Seattle

After Sam Baldwin’s wife, Maggie, dies, he and his son, Jonah, move from Chicago to Seattle for a change of pace. But once Jonah sees that Sam (Tom Hanks) is still lonely, he takes his father’s life in his own 8-year-old hands. This is the definition of a rom-com and feel good movie that everyone needs to watch on Valentine’s Day.


The Bridges of Madison County

This 1995 movie starring Meryl Streep and Clint Eastwood will get the toughest crying by the end of it. The film is adapted from the 1992 book with the same title, which is about an Italian-immigrant housewife who moves to Iowa and falls in love with a photographer for National Geographic.


My Best Friend’s Wedding

Julianne Potter (Julia Roberts) and her best friend, Michael O’Neal (Dermot Mulroney), had a deal that if they were both single by the time they were 28, they would marry each other. Four days before Julianne turns 28, she finds out that Michael is engaged to be married to a 20-year-old woman named Kimberly (Cameron Diaz). Julianne realizes that she doesn’t want Michael to marry anyone but her, so she plots a way to break up the wedding. This movie includes a very enthusiastic rendition of “I Say a Little Prayer” that is just begging to be emulated at actual weddings or rehearsal dinners as much as possible.


Notting Hill

Julia Roberts is a bit of a romance movie master. In this other beloved 1990s rom-com, Roberts plays a famous actress who just wants a normal life–I know, typical. In London’s charming neighborhood, Notting Hill, she meets an awkward British bookshop owner. This movie shows their relationship and how their lives are completely different, which becomes a roadblock for the two of them.


10 Things I Hate About You

Based on William Shakespeare’s “The Taming of the Shrew” and set in Seattle in the late 1990s, this movie takes 16th-century comedy to the Pacific Northwest grunge scene. Kat Stratford (Julia Stiles) is a highly intellectual teen who doesn’t have any interest in the irresponsible lifestyles of normal teenagers. She’s nicknamed “the shrew,” but her younger sister, Bianca (Larisa Oleynik), wants to date, go out, and be a normal high schooler. The only problem? Their father won’t let Bianca date unless Kat does. Cameron (Joseph Gordon-Levitt), a new student at the school, pays school bad boy Patrick Verona (Heath Ledger) to take out Kat so he can have a shot with Bianca. Nothing could go wrong with a deal like that, right?


Crazy, Stupid Love

At the beginning of this movie, Emily Weaver (Julianne Moore) tells her former high school sweetheart and husband, Cal Weaver (Steve Carrell), that she wants a divorce. Then, Cal pulls a full Ladybird and jumps out of the car, signaling how he feels about the whole thing. Enter Jacob (Ryan Gosling), who finds Cal wallowing at a bar and teaches him how to be a suave man of the 21st century. And y’all: that’s only about the first 15 minutes of the film.


While You Were Sleeping

This is technically a Christmas movie, but it does just fine for Valentine’s Day, too. It’s set in the cold Chicago winter, when transit worker Lucy Moderatz (Sandra Bullock) pulls her crush, Peter (Peter Gallagher) off the train tracks after he falls and hits his head. Peter ends up in a coma, and his whole family is under the impression that he and Lucy are engaged. Knowing that Peter doesn’t even know her name, Lucy decides to go along with it, and while he’s asleep in the hospital, she spends the holidays with Peter’s family. While Peter is sleeping, she also falls in love with Peter’s brother, Jack (Bill Pullman). This sounds like a lot to happen in one movie, but just trust that it’s a good one.



This plot is not unlike While You Were Sleeping in that it’s about a woman who falls in love with the brother of the man she’s supposed to be with. Widow Loretta (Cher) accepts a marriage proposal from her boyfriend, Johnny (Danny Aiello), but she falls for his younger brother, Ronny (Nicolas Cage). But this isn’t the only secret romance going on in this family. Cher won an Oscar for this one in 1988, and that was also the year of that famous Bob Mackie dress.


When Harry Met Sally…

Even the biggest rom-com defector cannot help but fall for Rob Reiner’s modern classic. With a script by the great Nora Ephron, and infectious and incredible chemistry between Billy Crystal and Meg Ryan, the film is arguably the greatest romantic comedy in movie history.


You’ve Got Mail

Nora Ephron’s remake of The Shop Around the Corner for the digital age stars Meg Ryan as a Manhattan bookseller whose business falters when a big-box bookstore run by a devious Tom Hanks moves into the neighborhood. But little do these enemies know, they have fallen in love with each other while communicating anonymously via email.


The Notebook

Based on the bestselling novel by Nicholas Sparks, this romantic tear-jerker stars Ryan Gosling and Rachel McAdams as two young lovers who are kept apart by their social circles—but still find a way to express their true love (particularly by kissing a lot in the pouring rain).



The classic drama is one of the greatest romantic movies ever made. Humphrey Bogart and Ingrid Bergman star as two former lovers who unexpectedly reunite in Morocco during WWII, and their reunion is disrupted when the woman needs her old flame’s help to escape—along with her new husband—to America.


Crazy Rich Asians

Rachel Chu (Constance Wu) has no idea that her boyfriend Nick (Henry Golding) comes from one of the wealthiest families in Asia. But she’s in for a rude awakening when she travels to Singapore to meet them—and butts heads with his impressive and intense mother (Michelle Yeoh).



James Cameron’s Oscar-winning masterpiece is one of the greatest technical feats in the modern Hollywood era, but it also features the compelling love story between a poor artist (Leonardo DiCaprio) and an upper-class debutante (Kate Winslet) who have an affair aboard the infamously doomed RMS Titanic.


The Princess Bride

Rob Reiner’s swashbuckling fairytale send-up, based on William Goldman’s novel, tells the tall tale of a farmhand named Wesley, his true love Buttercup, and the many wild and wacky individuals they meet on their long journey to live happily ever after.



This 1990 tearjerker proves that death isn’t the end of true love. When Sam (Patrick Swayze) is murdered during a mugging, his soul is trapped on Earth—which is how he discovers that his best friend is behind his death, and is already making moves on his girlfriend, Molly (Demi Moore). Sam soon enlists a psychic (Oscar-winner Whoopi Goldberg) to help him save Molly from peril.