13/02/2012 17:53 GMT | Updated 14/04/2012 06:12 BST

Top 10 Anti-Valentine's Day Movies

Whether you are single, celibate, widowed or blessed with possessing a healthy amount of hardened cynicism, the chances are that the 24-hour period between the 13th and 15th February is not one that you await with bated breath.

The tradition of being insufferably intimate and toe-curlingly cutesy in public places began during the war, when horny old Saint Valentine, the patron saint of making lonely people feel like shit, managed to get a particularly frigid young maiden to have sex with him by buying her a huge teddy bear with a love heart on it and an incredibly expensive piece of coloured card.

Okay, that's not true, but what do you care? Our advice is to lock the doors, get your unattached mates round, soak yourselves in low quality, supermarket liquor and settle in for a marathon of disastrous love stories so depressing, they would have Cupid himself raiding the medicine cupboard in an attempt to take his own life. Obviously the movie choices would vary depending on whether you possess a Y chromosome or not, so here are our Top Five anti-Valentines day movies for him and a Top Five for her.

For the boys

Crimes & Misdemeanors

This often-overlooked gem from 1989 is one of Woody Allen's finest. Crimes and Misdemeanors is a black comedy that offers two refreshingly bleak love stores. The first centres around a successful ophthalmologist named Judah, whose spontaneous affair with an air hostess begins to creep into his seemingly perfect family life. Things take a turn for the worse when his mistress (Angelica Huston) begins to blackmail him, forcing a desperate Judah to resort to extraordinarily sinister measures in order to silence her.

The second story revolves around Cliff, a filmmaker whose refusal to compromise his artistic integrity leaves him struggling financially and forces him to live in the shadow of his successful, yet utterly pompous brother-in-law, Lester (Alan Alda). Cliff quickly falls in love with Lester's producer and they begin to conduct and affair, however, she ultimately leaves him for the richer, more successful Lester, proving a valuable Valentine's Day lesson: no matter what they say, most women like men who are better looking, more affluent and more self-confident than you.


Terry Gilliam's 1985 masterpiece tells the story of a lowly office worker, Sam Lowry (Jonathan Pryce), who defies the oppressive totalitarian regime in which he lives, hoping to find the girl of his dreams, only to find out that in this case, love doesn't conquer all. In a world in which acts of the heart are strongly advised against, Sam dodges government goons and falsifies documents to save his lover from being arrested and shot on suspicion of being a terrorist, only to be rewarded by being strapped to a chair and tortured by an old friend. For a true anti-Valentine's day experience, be sure you are watching the 143-minute director's cut, which teaches another invaluable lesson in love: when gambling with love against the odds, the house will win every time.

Blue Valentine

If you are brave enough to leave the house this Valentine's Day, be safe in the knowledge that the vast majority of canoodling couples will see their relationship slowly collapse like a bouncy castle at a hedgehog's birthday party, before enduring an emotionally crippling breakup. Yes, you can take solace in the fact that most relationships will eventually show the signs of the all-too-familiar degenerative process that ends in misery, and this process has never been better depicted than in Derek Cianfrance's anti-love story Blue Valentine. Told in flashback between the embryonic and terminal stages of a relationship, this movie proves lesson number three: most relationships are doomed, and the chances are your next one will be too, so think yourself lucky that you won't be having to endure the slow and painful break-up process that awaits 80% of those annoying couples who steal kisses on the bus and hold hands over the coffee table.

Husbands & Wives

No one writes about relationships like Woody, so it is perhaps unsurprising that there are two of his films in this list. Made during the surfacing of Allen's controversial affair with co-star Mia Farrow's adopted daughter, the frosty atmosphere off-screen is just as palpable on it, as we are shown the story of two couples and the strains that their relationships are subjected to by deceit, infidelity, frigidity, jealousy and the ennui of domesticity. A brilliantly observed portrait of the nasty, spiteful and cruel sides of us that emerge when we're in love, Husbands and Wives teaches lesson number four: Despite what they tell you in Clinton Cards, love can bring out the worst in people.

Fatal Attraction

Admittedly this romantic dilemma will not happen to many of us in our lifetimes, but think of it as more of a 'worst case scenario'. After successful businessman Dan Gallagher (Michael Douglas) begins a steamy, passionate affair in a lift with a foxy young publisher (Glenn Close), his new mistress won't take 'no' for an answer when he attempts to break it off. This brilliantly 1980s thriller may be a little on the ludicrous side, but it does a good job of illustrating lesson number five: If you have an affair with someone, she will almost definitely blackmail you, steal your children and eventually come at you with a kitchen knife. Probably.

For the girls

Romeo and Juliet

If you're going to do Shakespeare, ladies, it's got to be in the capable hands of Baz Luhrman. Sequins, feathers, Leonardo DiCaprio before he developed a penchant for prosthetics and Krispy Kremes; what's not to love? Romeo and Juliet serves up a tasty melange of starcrossed lovers, unwavering adoration, marriage, frisky capers 'neath the sheets... so far, so much like a singleton's Valentine's Day nightmare. But after wide-eyed Romeo and Juliet (Claire Danes) have ogled each other through a fishbowl to the tortured strains of Desiree for a while, we tumble into a cataclysmic fog of poison, daggers, heartbreak and death. The lesson we all learnt today children? Don't be a prematurely smug couple.

Kissing Jessica Stein

In Charles Herman-Wurmfeld's quirky rom-com, Jessica Stein (Jessica Westfeldt) is a single girl about NYC, but unlike Carrie and Co, she's actually likeable - and more importantly, possesses a shoe-shopping budget you can relate to. Having sampled every type of bad man on the menu, she decides to experiment within the one relationship spectrum she previously left untouched... She kisses a girl, and much like Miss Perry years later, she likes it. This movie is for every singleton at the end of their tether with trawling through a catalogue of dating disasters- usually we joke about giving up and going for girls, but this is the story of a woman who stuck to her bisexual guns. And the implicit Valentine's lesson? Who needs men? Not Jessica Stein, and not Valentine's Day you.


Joe Wright's atmospheric adaptation of Ian McEwan's tragically romantic novel is a tangled web of forbidden love, war, manipulation and premature separation. If you're ready and willing to wallow in romantic depression, this is the Valentine's Day film for you. When ruddy-cheeked gardener Robbie (James McAvoy) and young lady of the manor Cecilia (Keira Knightley) succumb to a fledgling (yet oh-so secret) romance, Cecilia's younger sister Briony (Saorise Ronan) seems hell-bent on spoiling it for them, which she does, with sickening panache. It's doomed to fail from the start, but the twists and turns of McEwan's heartbreaking plot and the hopelessly dark denouement is bound to make any single-girl woes seem like child's play by comparison. Which is always a valuable Valentine's caveat. Just make sure the tissue box, or a mop, is within reaching distance.


Before the sickeningly saccharine arrival of Mean Girls, high school politics got its hands properly dirty in Michael Lehmann's Heathers. Taking revenge to a whole new level, bad boy J.D. (Christian Slater) drags his too-cool-for-school girlfriend Veronica (Winona Ryder) into a vengeful killing spree of all bitches, jocks and unsavoury characters in their High School- against her will! It's a classic Bonnie and Clyde tale, and Veronica can neither live with or without him. Surprisingly, considering it's rather bloody subject matter, it's also rosé-splurtingly funny, and has one of the best 'girl power' endings in the history of high school movies. Plus, lest we forget, it carries one of the most important anti-Valentine's messages of all: sometimes you really are better off without him (especially if he's a gun-wielding psychopathic murderer).

Rules of Attraction

You know when a movie starts with a guy chucking up on a girl's back while she recklessly loses her virginity to him at a college party, it's no love story. The wildly hedonistic students of Camden college do what they want, when they want, to who they want, and eventually, get exactly what they deserve in return. Virginal Lauren (Shannyn Sossamon), drug addled Sean (James van der Beek) bi-sexual deviant Paul (Ian Somerhalder) and slutty cheerleader Lara (Jessica Biel) are but a few of the unsavoury characters messing up each other's lives and screwing around with everyone's hearts in this mess of coke-fuelled debauchery. The valuable Vaentine's lesson? Love is messy, love hurts, and it's probably best you've only got a bottle of wine to cuddle up to tonight- at least it'll only be a bit mean to your liver.