Top 10 Best Anti-Valentine’s Day Movies

By Lauren DuBois,

For some, Valentine’s Day is not a good day. For some of the single and lonely, it’s a sappy reminder that they have no one to spend the one day of the year devoted to solely to love with. For others, it’s just an unnecessary day that isn’t a holiday at all, but a day created in a joint effort by Hallmark, 1-800-flowers, and Hershey’s chocolate to boost sales. Needless to say, these people don’t usually buy into the fancy dinners, or snuggling in to watch romantic comedies. So for those people, here’s a list of the top 10 movies to watch instead: either they’ll be a good reminder that sometimes being single isn’t so bad, or at the very least, serve as a good way to perfectly counteract all of the romance of the day.

10. Swimfan: Starring Jesse Bradford, Erika Christensen and Shiri Appleby; Dramatic Thriller, 85 min; 2002

High School senior Ben Cronin has a promising swimming career and a loving long-time girlfriend, Amy. When new girl Madison Bell moves to town, she expresses interest in Ben, and ultimately seduces him. Ben learns after he blows her off though that there will be consequences, as Madison begins to stalk him, and threatens to ruin his life in any way possible—whether she ruins his being scouted by Stanford, or kills his girlfriend, she will stop at nothing until she gets Ben for herself. This movie is perfect for an Anti-Valentine’s watching not only because of its sadistic stalker storyline, but because it was abysmally bad at the same time. Nothing’s better for making you forget its Valentine’s Day than not just watching a movie about stalkers, but a bad one at the same time.

9. Blue Valentine: Starring Ryan Gosling, Michelle Williams and John Doman; Dramatic Romance, 112 min; 2010

Cindy and Dean Heller are a young, working class married couple trying to eke out the ravages of the life they’ve built together. Though both do work, there is exceptional baggage weighing their relationship down—Cindy’s dysfunctional family and past profound relationship are affecting how she sees Dean, while Dean’s own dysfunctional past and drinking problems are affecting how he sees Cindy. In a last-ditch effort to save their marriage by seeing if it can survive their many issues, they take a weekend getaway together. While this movie does have romantic elements to it when it chronicles the early days of Cindy and Dean, it’s a perfect reminder that love can disintegrate over time—and sometimes it just isn’t enough to make a relationship work.

8. The Break-Up: Starring Jennifer Aniston, Vince Vaughn and Jon Favreau; Romantic Comedy, 106 min; 2006

Brooke and Gary are finished with their two-year relationship. But one thing remains at a high-stake: their shared condo—and neither one of them want to move out. In an effort to keep making one another jealous, a ridiculous war of the sexes escalates until finally, enough is enough. It might seem like a movie touted as a romantic comedy, which also happens to star the queen of romantic comedies, Jennifer Aniston, is an odd choice for an Anti-Valentine’s Day movie. But this isn’t like usual Hollywood Romantic Comedies, featuring an atypical sort of happy ending. So don’t be afraid to watch.

7. The Way We Were: Starring Barbra Streisand, Robert Redford and Bradford Dillman; Romantic Drama, 118 min; 1973

Katie and Hubbell are from two different worlds: in college, she’s a political activist, and he’s a popular athlete. When they meet up again 20 years later, she’s still an activist, and he’s a novelist and military man. The two decide to pursue the relationship that never got started between them in college, but not without sacrificing parts of themselves along the way in hope of holding on to what they have. Eventually, after several obstacles over the years prove it to them, they realize that their relationship was never meant to be, that they’ve always desired different things and can’t build a life together on the lies they tell themselves. They go their separate ways for good. This seven-time Oscar nominated movie is also one of the saddest movies in movie history. So for the recently single person still aching from a broken heart, this is the perfect movie to get out that good cry that you’ve been holding back, and maybe as a result, you’ll start to let go and move on.

6. Cruel Intentions: Starring Sarah Michelle Gellar, Ryan Phillippe and Reese Witherspoon; Romantic Thriller, 97 min; 1999

Kathryn, a drug-addicted and highly sexual girl makes a bet with her step-brother Sebastian that he won’t be able to bed Annette, a saintly good-girl who wants to wait until marriage. If he loses the bet, Kathryn wants his car. But if he wins, he wants Kathryn. Based on a disgusting relationship rooted in the step-siblings constantly trying to one-up and seduce the other one, this movie is equal parts trashy as it is sadistic, and no one gets their happily-ever-after. Why wouldn’t it be the perfect choice for an Anti-Valentine’s Day movie showing?

5. High Fidelity: Starring John Cusack, Iben Hjejle and Todd Louiso; Comedy, 113 min; 2000

Rob Gordon, a record store owner and compulsive list-maker, recounts his top five breakups, including the one in progress. As he recalls each breakup, he reconnects with his former loves to find out why it is they dumped him, in an attempt to find out where he’s gone wrong, and what exactly has made him lose his current love. This movie is good for the guy who is alone on Valentine’s Day, or just the person who wants something a little more humorous and light to watch instead.

4. Vertigo: Starring James Stewart, Kim Novak and Barbara Bel Geddes; Mystery Thriller, 128 min; 1958

Police detective John “Scottie” Ferguson is asked by an old college friend to look after his wife Madeleine, after he fears she is going insane and contemplating suicide, As Scottie follows her, he ultimately falls in love, and she appears to as well—until they travel to an old mission church and he fails to stop her from jumping to her death due to his intense vertigo. Several months later, Scottie meets Judy Barton, a woman who is the spitting image of Madeleine. As he tries to re-make Judy into Madeleine by getting her to dye her hair and change her clothes, he begins to realize though that he had been duped and was just a pawn in a complex plot meant to end in tragedy. An Alfred Hitchcock classic, this, or any of the other movies brought to Hollywood by the “Master of Suspense,” would be ideal for an anti-Valentine’s day movie marathon.

3. (500) Days of Summer: Starring Zooey Deschanel, Joseph Gordon-Levitt and Geoffrey Arend; Romantic Comedy, 95 min; 2009

Tom believes in true love. Summer doesn’t believe true love actually exists. They’re the least likely people to make a relationship work—and yet, they somehow still pursue one. But naturally, it begins to fall apart, and the audience is forced to watch as Tom alternates between replaying their entire relationship in his head, and then goes through the several stages of after-break-up grief. Though the movie is somewhat of a feel-good type despite its unconventional ending, it’s still good for an Anti-Valentine’s Day movie because of how it deals with the topic of breaking up. On a personal level, I watched this movie on Valentine’s Day one year with my best friend to help her get her mind off of her recently-ended engagement—and it worked like a charm. While a part of her was still sad because of her ended relationship, the movie helped remind her that she wasn’t the only person who had ever been dumped before—and that she would one day move on.

2. Fatal Attraction: Starring Michael Douglas, Glenn Close and Anne Archer; Dramatic Thriller, 119 min; 1987

Happily married lawyer Dan Gallagher has a one-night stand with colleague Alex Forrest, but he quickly learns how much it will come back and haunt him when she begins to stalk him and his family. Just how far will Alex go to get her man? Sorry for the possible spoiler, but she actually boils the family rabbit. Sadistic enough for you to watch for your Anti-Valentine’s Day movie viewing experience? Yeah, I thought so.

1. American Beauty: Starring Kevin Spacey, Annette Bening and Thora Birch; Drama, 122 min; 1999
Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after he develops an infatuation, and begins to pursue a relationship with, his daughter’s attractive friend. As his mid-life crisis plays out, lives change, and not for the better. This darkly comedic drama is good for someone who is spending the day solo because it gives a glimpse behind the hypothetically perfect white picket fence that we’re supposed to dream of when we’re not single. So maybe it’s a good reminder that being single isn’t really all that bad after all.

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