The chronologically jumbled story of a lovelorn greeting card writer (Joseph Gordon-Levitt) and the girl who drags his heart around (Zooey Deschanel) was a sleeper hit in 2009 and put director Marc Webb (The Amazing Spider-Man) on the map. For everyone who has put everything into a relationship, only to have the other person suggest maybe it would be better if you were just friends who enjoyed architecture and pancakes together, this one's for you.
Lester Burnham (Kevin Spacey) pleasures himself in a shower and conducts a rose-petal-strewn fantasy affair with his daughter's high school friend as his wife (Annette Bening) gets busy in a motel room with a co-worker in this five-time Oscar winner from 1999. It doesn't end well for Lester, but then, it didn't start too well for him, either.
Watch the air slowly deflate from the marriage of Cindy (Michelle Williams) and Dean (Ryan Gosling), a pre-med student and the high school dropout who sweeps her off her feet, in this partly improvised, boy-loses-girl love story from 2010. It's at times stomach-wrenchingly difficult to watch. Perfect! No bluer Valentine has there ever been.
Based on Patrick Marber's award-winning play, 2004's Closer pits four unfaithful people, strangers, lovers and spouses, inside a sexual Rubik's Cube from which no one emerges unscathed, unscorned or unsatisfied.
The Bride (Uma Thurman) is driven by one motivation: revenge, meted out against the man who shot her in the head on her wedding day. Hopefully, whoever broke your heart wasn't quite so cold-hearted about it, but there's nothing like some Quentin Tarantino-envisioned bloodshed, which flows deeply in this 2003 film, to get you back on your feet again. And don't forget Kill Bill Volume 2, which came out one year later.
The 1962 classic American novel from Richard Yates got a film adaptation in 2008 from (sensing a pattern?) American Beauty director Sam Mendes. Set in the late 1940s and 1950s, it's the story of Frank Wheeler (Leonardo DiCaprio) and April (Kate Winslet), a couple in suburban Connecticut living less than a picture-perfect life. Frank's cheating, an unwanted pregnancy and its tragic aftermath should all be enough to throw some cold water on any touchy-feely thoughts.
Michael Fassbender plays Brandon, an ad exec with a secret addiction — sex, baby! — in this 2011 drama. Luckily, he lives in New York City, home to approximately 4 million other sex addicts.
Brooke (Jennifer Aniston) and Gary (Vince Vaughn) meet at a Chicago Cubs game, then quickly fall in love and purchase a condo together. When the relationship crumbles, they try to stick it out as roommates — until they do everything they can to get the other to move out. This 2006 film is a perfect bitter cocktail for anyone who's co-habitated, then found themselves packing up boxes and fighting over dog-visitation rights.
Hey, it's right there in the title. This 2002 drama from Fatal Attraction director Adrian Lyne stars Richard Gere and Diane Lane as Edward and Connie, a married couple from suburban New York who lack a spark. The jezebel in this instance is a French man — the dashing Olivier Martinez, who Connie meets on the street, and the two quickly embark upon a steamy and torrid affair. Things don't end well.
Probably the Citizen Kane of anti-Valentine's Day movies, this 1989 film directed by Danny DeVito stars Michael Douglas and Kathleen Turner as Oliver and Barbara Rose, the most acrimonious divorcing couple in history. This one will make you stand up and cheer for how much love sucks.