If you've been a faithful listener of my radio show over the years or subscribed to my podcast, you already know one thing about me—I hate Valentine's Day.
Every year, during my time on WGN, I made it a tradition to host an Anti-Valentine's Day Show, a glorious counterprogramming to all the forced romance, overpriced dinners, and Hallmark nonsense being shoved down our throats.
So, in keeping with that tradition, I'm sharing my list of the 10 best anti-Valentine's Day movies.
Look, I get it—some people love Valentine's Day, and that's fine. If you want to spend the night watching "The Notebook" and feeding each other chocolate-covered strawberries, go for it. And hey, I'll admit, now that I have a girlfriend who I genuinely love, maybe my stance has softened a little. But not really.
Here's the thing: Valentine's Day, as a concept, is ridiculous. It's a manufactured, over-commercialized guilt trip designed to make us feel obligated to be romantic, even when we've had a crap day.
Car broke down? Still gotta be romantic. Had a miserable time at work? Suck it up and buy those flowers. Just not feeling it? Too bad—it's Valentine's Day, and you must feel the love.
No, thanks.
So, if you're like me and you'd rather watch a movie that reminds you that love can be painful, ridiculous, suffocating, or just flat-out awful, then this is the list for you.
These aren't your typical "bad romance" movies—these are the films that highlight the ugly side of love, the heartbreak, the toxicity, the chaos, and the moments that make you question why people even bother with relationships at all. Some of these are depressing, some are brutal, and some are hilarious, but they all make for perfect Anti-Valentine's Day viewing.
My 10 Favorite Anti-Valentine's Day Movies
These are in no particular order and feature clips that give you a little taste of their unapologetic anti-Valentine sentiment. WARNING: some of these are very adult in nature.
1. BLUE VALENTINE (2010)
This movie will destroy you. Derek Cianfrance's "Blue Valentine" is a heartbreakingly raw look at the rise and fall of a relationship, told through two interwoven timelines—one showing the giddy, hopeful early days of love, the other showing the ugly, bitter breakdown of a marriage. Ryan Gosling and Michelle Williams give some of the most devastating performances you'll ever see, and the film's bleak cinematography only adds to the emotional gut punch. If you want to be wrecked on Valentine's Day, this is the movie to watch.
2. CLOSER (2004)
Mike Nichols' "Closer" is a brutal, cynical takedown of love, relationships, and human nature. Featuring an all-star cast (Julia Roberts, Jude Law, Clive Owen, and Natalie Portman), the film follows four people as they cheat, manipulate, and emotionally destroy each other in a tangled web of lies and betrayal. If you've ever suspected that love is just a slow-motion car crash waiting to happen, this movie will confirm all your worst fears.
3. MIDSOMMAR (2019)
Ari Aster's "Midsommar" is one of the best breakup movies ever made. Sure, it's a horror film, but at its core, it's about a woman (Florence Pugh) trapped in a toxic relationship with a self-absorbed, emotionally unavailable boyfriend. By the time the actual horror kicks in—with ritual sacrifices, bizarre ceremonies, and gruesome deaths—you realize that the scariest part of the movie isn't the cult but the relationship itself. That final smile from Florence Pugh? Absolute perfection.
4. GONE GIRL (2014)
David Fincher's "Gone Girl" is a thriller, mystery, and psychological mind game. But above all, it is one of the most disturbingly accurate movies ever made about marriage. Rosamund Pike is chilling as the brilliant, sociopathic Amy Dunne, who meticulously orchestrates the ultimate revenge against her cheating husband (Ben Affleck). Twisted, darkly funny, and completely inappropriate for Valentine's Day, this movie reminds you why marriage can be downright terrifying.
5. MODERN ROMANCE (1981)
Albert Brooks is a genius, and "Modern Romance" is one of his best. It's a brutally honest, painfully funny look at a neurotic, jealous, obsessive man who can't handle relationships—yet keeps diving right back in. Playing a film editor in Hollywood, Brooks captures the absolute insanity of love, especially for people who are insecure, possessive, and completely unable to function like normal human beings in a relationship. It's hilarious, sad, and the perfect reminder that sometimes, it's just better to be single.
6. MARRIAGE STORY (2019)
Divorce is never fun, but "Marriage Story" takes it to a whole new level of emotional devastation. Noah Baumbach's film follows Adam Driver and Scarlett Johansson as they navigate the painful, legal, and emotional mess of ending a marriage. The performances are incredible, the writing is brutally honest, and this movie will feel way too real if you've ever gone through a divorce. One particular argument scene between Driver and Johansson is so raw and painful that it'll make you want to avoid relationships altogether.
7. WHO'S AFRAID OF VIRGINIA WOOLF? (1966)
Think you and your partner fight a lot? Think again. George and Martha, played to absolute perfection by Elizabeth Taylor and Richard Burton, redefine dysfunctional relationships in "Who's Afraid of Virginia Woolf?" Based on Edward Albee's play, the film is basically two hours of a couple tearing each other apart in front of two unsuspecting guests. It's dark, intense, and somehow hilarious in the most twisted way. Watch this, then take a deep breath and be grateful your relationship isn't this bad.
8. MANCHESTER BY THE SEA (2016)
If you want an uplifting love story, this movie is not for you. "Manchester by the Sea" is an absolutely devastating portrait of grief, loss, and a relationship that crumbles under the weight of tragedy. Casey Affleck and Michelle Williams (again—apparently, she loves heartbreaking movies) deliver gut-wrenching performances that will leave you emotionally shattered. If you're in the mood to cry uncontrollably on Valentine's Day, this is the movie to watch.
9. LA LA LAND (2016)
For most of its runtime, "La La Land" feels like a joyous celebration of love, music, and old-school Hollywood musicals. Then, the ending happens. Damien Chazelle's dazzling, beautifully shot film lures you in with its charm and incredible musical numbers, only to hit you with a heartbreaking finale that reminds you that timing is everything in relationships. Sometimes, love just doesn't work out the way you want it to, and that's what makes this movie the ultimate bittersweet romance.
10. THE WAR OF THE ROSES (1989)
I saved the best for last. "The War of the Roses" is my favorite Anti-Valentine's Day movie of all time. Directed by Danny DeVito, this pitch-black comedy follows Kathleen Turner and Michael Douglas, a once-loving couple who slowly descend into pure, unfiltered hatred. Their marriage deteriorates into an all-out war, complete with insane fights, property destruction, and, ultimately, their own demise. This movie does not pull punches—it gets ugly, it gets violent, and it is hilarious. If you want a movie that takes the phrase "till death do us part" literally, this is it.
Happy Anti-Valentine's Day!
So there you have it—10 movies that will make you rethink love, relationships, and everything in between. Whether you're single, recently dumped, or just sick of all the Hallmark nonsense, these films will provide the perfect counterprogramming to the usual Valentine's Day sap.
So forget the roses, skip the candlelit dinner, and dive into these dark, twisted, and brutally honest looks at love gone wrong. You'll either be grateful for your relationship or be very happy you're single.
Happy Anti-Valentine’s Day!
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