The 6 Best Break-Up Movies for Valentine's Day

For some, Valentine’s Day is a sweet holiday full of roses, chocolates, lovely dinners, and over-the-top romantic gestures. Some people take this opportunity to get engaged, or even married, and it forever remains an important day for the happy couple.

But the rest of us… well that’s a different story. In the very best case scenario, Valentine’s Day is just another day and maybe involves a Hallmark card and a glass of champagne. At its very worst, the big day can rummage up bad memories of broken hearts and relationships that were simply never meant to be. If you happen to be in this last category, then the last things you want to see on February 14 every year are hearts and happy couples.

For you, we have rounded up the best, most anti-Valentine’s Day movies we could find. Here we have the top break-up movies around. Be aware, though, that spoilers abound.

Which camp are you in? Let us know in the comments!

6. The Break-Up

It doesn’t get more literal than this. Here we have Gary (Vince Vaughn) and Brooke  (Jennifer Aniston), a couple that simply cannot make it work. She’s too controlling, he’s too immature, and they can’t meet somewhere in the middle, despite still loving each other. They end up needing to share their condo during their split, which adds to the awkwardness of the situation. While the audience is rooting for them and holds out hope for a last-minute reconciliation, nothing comes of it. This couple is simply not meant to be.

5. Eternal Sunshine of the Spotless Mind

Ever been in a relationship (and through a breakup) that hurt so much you wish you could just erase it from your memory? If you were in this film, you could do just that. This love story (with a side of science fiction) gives us low-key Joel (Jim Carrey) and quirky Clementine (Kate Winslet) who randomly decide to head out to Montauk one day. They find each other, only to later learn that they had previously been lovers and had their memories of each other erased following their painful breakup. This film gives us a bit of hope though. Perhaps they are meant to be together after all.

4. Closer

This star-packed film from 2004 is chock-full of relationships, break-ups, cheating, and divorces among four generally unhappy people: Anna, Dan, Alice, and Larry. At any given moment, someone is seducing another person’s lover or lying about his or her current situation. It’s a tangled mess, and somehow accurately captures the feeling of some of life’s harshest, most raw moments.

3. (500) Days of Summer

We really really want Summer (Zooey Deschanel) and Tom (Joseph Gordon-Levitt) to make it work. They’re adorable together and we progress through their relationship right along with them. Somewhere around day 290, it becomes apparent that things aren’t going to work out. We spend the next two-hundred days or so following Tom’s attempts to win back his girl. But she has, of course, moved on. And finally, we see Tom get his chance at true love as well — in the form of a new woman named, of all things, Autumn.

2. Forgetting Sarah Marshall

Poor Peter (Jason Segel) just can’t win when it comes to Sarah (Kristen Bell). The two have been together for years, but she completely surprises him when she breaks up with him. In his attempt to get over her, Peter takes the trip to Hawaii that the two were supposed to take together. Unfortunately for him, Sarah is right there at the same hotel — with her new lover Aldous (Russell Brand). Peter learns that Sarah has been cheating on him with Aldous for a while, and he does everything he can to move on with his new flame, Rachel (Mila Kunis), who works at the hotel. While this is absolutely a movie about breaking up, it’s also very funny and a great option to watch without getting too depressed this Valentine’s Day.

1. Gone Girl

Amy (Rosamund Pike) is so over her husband Nick (Ben Affleck) that she goes so far as to fake her own death and then frame him for the murder. Talk about wanting to end a relationship. The steps that this sociopath takes to make her disappearance as meticulous as possible are impressive. The movie quickly becomes more about the mystery of her disappearance than the disintegration of their relationship. But in the end, it seems that they deserve each other.