Movies
The Weekly Listicle: Worst. Dates. Ever.
This weekend marks the release of Date Night, starring Steve Carrell and Tina Fey, two of the funniest people in the world, and directed by Shawn Levy, who after decades in the industry has yet to direct a funny movie. So while you’re waiting to see if those polar opposites balance each other out (and preferably lean towards the “funny” side), The Weekly Listicle presents our own picks for the Worst Dates in Film History.
As always, The Weekly Listicle represents the personal preferences of Julia Rhodes and myself (William Bibbiani!), and narrowing it down to two choices per critic was a particularly daunting task this week. It’s a rare film that doesn’t include at least a little romance, and in order to make that romance dramatic and unexpected a lot of things usually go wrong with the courtship process. From Travis Bickle’s unfortunate taste in movies in Taxi Driver, to history’s second most ill-fated prom night in There’s Something About Mary (see Julia’s picks for the absolute worst), there was no shortage of embarrassing and catastrophic dates to choose from.
William’s Picks:
PLAY IT AGAIN, SAM (dir. Herbert Ross, 1972)
Yes, that poster in the background sort of says “Hump Across the Pacific.” You might be reading a little too much into that.
Play It Again, Sam is the Woody Allen movie that everyone forgets wasn’t actually directed by Woody Allen. Sure, the Woodman wrote the script (based on his own play), and stars as his most common film persona, a nebbish everyman immersed in a culture he doesn’t quite understand. Play It Again, Sam also marked the first time Woody Allen appeared alongside frequent collaborator Diane Keaton, whom he would later direct to an Oscar for Annie Hall. The film is full of amusing insights into the “modern” dating process and packed with hilarious set pieces. That the film was actually directed by Herbert Ross (Footloose, The Goodbye Girl, and the underrated My Blue Heaven) feels incidental. The film is intrinsically Woody Allen regardless of who actually sat behind the camera, much like The Nightmare Before Christmas is still “Tim Burton’s” regardless of the work of Henry Selick.
Of course, over the past five decades Woody Allen has had as much to say about romance as any other writer or filmmaker, and probably more, so it would be easy to populate any list about “Film’s Worst Dates” almost exclusively with scenes from his works. (Haven’t we all sneezed into the cocaine at some point?) If anything, this selection from Play It Again, Sam marks a purely personal choice, as the scene is a bit of a throwaway gag that has nevertheless stuck with me for years because I’ve been in almost this exact same situation before, and practically every man I’ve discussed it with has sympathized as well.
Allan Felix (Woody Allen) gets valuable advice from Humphrey Bogart (Jerry Lacy) on how to act like a real man in Play It Again, Sam.
In Play It Again, Sam, Woody Allen plays Allan Felix, a recent divorcee who – thanks to the goading of his friends Linda (Diane Keaton) and Dick (Tony Roberts, another frequent Allen collaborator) – re-enters the dating scene to disastrous results. Like most of us, Allan feels the need to put on an act during the courtship process as he feels that his actual persona would be unappealing to the opposite sex. His attempts to become seductive and sophisticated are personified in his conversations with the ghost of Humphrey Bogart (Jerry Lacy, better known for his roles on TV’s “Dark Shadows”). Bogart attempts to give Allan dating advice, but Allan eventually finds himself attracted to the only woman with whom he feels like he can be himself: Linda, who of course is tragically married to Dick.
Unlike most romantic comedies, which depict the trials and tribulations of a protagonist and maybe two or three love interests before the hero finds true love, the protracted dating sequences of Play It Again, Sam illustrate a more universal dating experience. Allan has to suffer through an embarrassing number of embarrassing dating scenarios before realizing what he really wants, both from a partner and from himself, which is a pretty common experience as near as I can tell. But in the film’s highlight Allan finds himself in the apartment of a self-professed nymphomaniac, and things go horribly awry.
Let’s watch:
Misreading the moment in which to make your move is one of the most common dating flubs imaginable, and as usual (in his early days) Allen’s exaggeration for comedic effect only makes the experience more universal. It’s also really, really funny.
SHAOLIN SOCCER (dir. Stephen Chow, 2001)
Boot the to the head: Writer/Director/Star Stephen Chow breaks into Western Pop Culture in the witty, exciting and only occasionally unpleasant Shaolin Soccer.
Shaolin Soccer was the film that brought Chinese superstar comedian Stephen Chow (who later directed the also-wonderful Kung Fu Hustle) to America’s attention for the first time, and it’s easy to see why once you familiarize yourself with his earlier films. Besides being steeped in Chinese culture (nothing wrong with that, but it doesn’t translate very well to most Western audiences), there’s an unfortunate undercurrent in a lot of his work that can easily turn me off on a personal level.
You see, Chow’s films often feature a cartoonish level of oppression and violence towards his protagonists which create both comedic situations and sympathy for his unjustly persecuted everymen. But sometimes it really feels like he goes too far in the persecution of his female characters, like in the case of God of Cookery, an otherwise laugh-out-loud hilarious broad comedy starring Chow as a Martha Stewart-like cooking mogul who falls from grace and fights his way back up again. Along the way he befriends but is disgusted by the face of the usually lovely Karen Mok (So Close), a lowly street vendor who was horribly scarred when she defended Chow’s reputation in a street fight. When Mok finally declares her love for Chow, he literally runs to the ends of the earth to avoid her. Although he realizes the error of his ways, the film nevertheless ends with his elation that she finally had plastic surgery to fix her face. It’s an uncomfortable note on which to the end the film, and a big part of the reason why I don’t think it’s as popular as Shaolin Soccer.
In Shaolin Soccer, the ridiculously beautiful actress Wei Zhao does a little Tai Chi Baking.
This unfortunate tendency is muted in Shaolin Soccer, which co-stars Wei Zhao (Red Cliff) as Chow’s love interest, Mui. The film tells the story of a downtrodden group of martial arts masters who attempt to bring martial arts to the world of professional soccer. Chow lovingly portrays the martial arts as magical in their potential to improve lives and make sporting events in particular so exciting that I myself might actually watch them (as it stands I prefer sports films to sporting events themselves, but that’s a topic for another time). It’s an exhilarating and often wonderful film that deservingly brought Chow to worldwide attention, but it’s the love story that we’re here to discuss today.
Wei Zhao plays another beautiful but scarred street vendor in Shaolin Soccer, this time a clearly beautiful woman with horrible acne who uses Tai Chi in her cooking. Chow, playing Mighty Steel Leg Sing, is immediately intrigued by this woman who, like him, uses martial arts in unusual ways. But although Chow’s character is supportive of Mui, Chow the director has a bit more cruelty in store for her. Her disastrous attempts to beautify herself are met with painful derision by the entire cast (in a scene usually cut from American releases, and with good cause), but it’s their date in an empty shopping mall that blurs the line between hilarity and discomfort the most.
Getting rejected sometimes feels like a slap in the face. You know what else feels like a slap in the face? A slap in the face.
Since Mui and Sing are both extremely poor, the opportunity to even touch a beautiful dress qualifies as a dream-come-true date for her as Sing shows her around a beautiful shopping mall after closing time. Unfortunately, there’s a fly buzzing around, and Sing slaps her repeatedly – and very, very hard – in an attempt to kill the tiny beast. Mui’s crippling low self-esteem is in full effect, and it doesn’t even occur to her to question whether the slapping was entirely necessary. To make matters worse, it turns out that Sing doesn’t even love Mui – he just respects her as a friend – so this date sucked on many levels for her. Shaolin Soccer is an otherwise wonderful film, but this really qualifies as one of the crappiest dates in film history.
10 THINGS I HATE ABOUT YOU (dir. Gil Junger, 1999)
In terms of bad dates, Shakespeare’s “The Taming of the Shrew” is ripe material: an obdurate, ball-busting woman, a self-obsessed suitor, a bungled courtship ritual, and of course, a love story. Teen movies (the decline of which I lamented a few weeks ago) are full of terrible dating experiences, because, well, we all had them. Gil Junger’s 10 Things I Hate About You, which is based on “The Taming of the Shrew,” has the benefit of great writing and a wonderful cast. The play is of course problematic; the idea that an independent woman must be “tamed” is horrifically misogynistic. Of course, savvy writers with a good sense of humor manage to make it less offensive–as English teacher Mr. Morgan says following an impromptu rap of Sonnet 141, “Shakespeare’s a dead white guy, but he knows his sh*t.”
A face-off between the bad boy and the shrew. (Ledger, Janney, and Stiles in 10 Things I Hate About You.)
The “mewling, rampalian wretch” Kat (Julia Stiles) is a self-professed feminist who likes “Thai food, feminist prose, and angry girl music of the indie rock persuasion” (sounds a bit like a certain CLR reviewer). As we all know, these traits are a massive threat to teenage boys. Vain, self-obsessed Joey Donner (Andrew Keegan) decides to “conquer” Kat’s lovely, vapid little sister Bianca (Larisa Oleynik), but because of rules imposed by their overbearing OB-GYN father (Larry Miller), Joey has to get Kat to date first. Joey and sweet newcomer Cameron (Joseph Gordon-Levitt, who later transformed into an incredible actor) combine forces to pay Australian bad boy Patrick Verona (posthumous Oscar winner and former heartthrob Heath Ledger) to take Kat on a date. As you’d imagine, this kind of ass-backwards scheming leaves the court wide open for the kind of date where everything that can go wrong will go wrong. This disastrous date would, of course, happen on the date night to end all date nights, the prom.
Scheming pretty boys: Ledger and Keegan in 10 Things I Hate About You.
As with most of the indulgent late-90s teen movies, the prom is ridiculously posh and features girl-rock staples Save Ferris and Letters to Cleo. Huge, neon pink, puffy dresses, horrible up-dos, and white tuxes abound. Kat agreed to attend Prom with Patrick, who has been accepting money from Joey the whole time, which means Bianca can go with Cameron. When Joey sees Bianca and Cameron together, he goes crazy. Cameron’s friend Michael sidles over, Shakespeare-obsessed date in tow, to mutter, “The sh*t hath hitteth the fan…eth.”
“I have a dick on my face, don’t I?” Cameron (Gordon-Levitt) and Michael (David Krumholtz).
Indeed, sir, indeed. Cameron sticks up for Bianca and Joey clouts him. Enter sweet Bianca, who administers Joey two hard jabs to his precious nose-spray-ad schnoz, then a kick in the balls for good measure. It’s pretty satisfying to watch a girl in a pink dress deck a guy who deserves it. As these movies do, all ends well. Kat reads a terrible poem she wrote for Patrick in class. Patrick buys Kat a Fender Strat so she can start her own band. Though she admonishes him that he can’t just buy her a guitar every time he screws up, they end up together, because after all, they’re actually in love.
CARRIE (dir. Brian de Palma, 1976)
Carrie has the perfect date: a tiara, a bouquet, the class stud.
Though Date Night is about an actual one-on-one date debacle, once I wrote about 10 Things I Hate About You prom was on my mind. And what comes to mind when you think bad prom nights? Carrie. Based on Stephen King’s first novel, Brian de Palma’s 1976 flick Carrie is the most nightmarish, horrific example of just how badly a date can go wrong. The film follows a downtrodden young girl as she attends her first prom, gets her first kiss, and enjoys the first signals that her life may turn itself around. Then things go straight to hell.
Carrie White (Sissy Spacek) is a homely teenager whose crazy, religious fanatic mother Margaret (terrifically creepy Piper Laurie) believes breasts and menstruation are signs that the devil is in you. Of course Carrie grows up without an ounce of social aptitude, and her classmates bully her mercilessly. With their ‘70s feathered hair, halter tops, miniskirts and booty shorts, Carrie’s contemporaries are vapid, cruel stereotypes—unfortunately not so far off from the kind of girls many of us encountered in high school. Class queen Sue Snell (Amy Irving) feels guilty for her part in a locker room humiliation and asks her boyfriend Tommy Ross (William Katt) to take outcast Carrie to the prom. When spoiled harpy Chris Hargenson (de Palma partner and staple Nancy Allen) hears this plan, she devises her own scheme to dump pig’s blood on Carrie at the prom. Once again with the scheming. Unbeknownst to any of them, Carrie’s recent menses came with a dose of telekinetic powers, and she’s on the precipice of insanity.
This is what you get for breaking curfew: Piper Laurie in Carrie.
De Palma’s style is derivative (he’s got a reputation as a Hitchcock copycat), and in the seventies he employed a lot of gimmicky techniques, particularly split screen and soft focus halo effects. Though they date the movie, they successfully create complete and utter horror. After initial suspicion of his motives, Carrie accepts Tommy’s offer. She spends hours upon hours sewing a lovely, floaty white dress for herself, and after a massive battle with her mother, leaves for the prom. Tommy, actually a genuinely kind person, treats Carrie to the best night of her life. Even her classmates begin to accept her in earnest. Tommy and Carrie dance as the camera swirls around them dizzyingly, and they share a kiss. After the tense, dismaying opening of the film, it’s hard not to feel a bit warm and fuzzy. Carrie’s life finally seems to be turning around.
Prom night gone terribly wrong: Sissy Spacek in Carrie.
What follows is a scene of classic horror. Chris Hargenson sets it up so Carrie wins Prom Queen—a delicious capper to a lovely evening—and when Tommy and Carrie mount the stage de Palma alternates between slow motion shots of Carrie’s happy acceptance backed by sweet orchestral music, and overhead shots of the bucket of blood. When Hargenson pulls the cord Carrie is sheathed in gore. She hears her crazy mother shrieking that classic line, “They’re all going to laugh at you!” Spacek’s eyes widen until she appears demonic; the blood congeals slowly to form a sticky jacket. The heavy bucket drops on Tommy’s head, killing him (talk about a nightmare date). Carrie directs her gaze toward the doors, slamming them shut, and the lights, turning off all but the sickly red spots. In split screen, we see Carrie’s insane visage on the left and the results of her powers on the right. She stands frozen onstage while the gymnasium comes alive around her, inanimate objects murdering her classmates. She lights the gym on fire and stalks outside, untouched by the flame, coated in gore, her eyes luminescent in the gloom.
In the novel, Carrie blows up the entire town and stops her mother’s heart. The film ends with a more obvious, though seriously impressive, murder scene. Everyone gets his or her due, whether they deserve it or not. This date ends in hell on earth. Most of us, despite some terrible dates, can’t quite say that.

William Bibbiani is a highly opinionated film, TV and videogame critic living in Los Angeles, California. In addition to his work at the “California Literary Review” William also contributes articles and criticism to “Geekscape” and “Ranker” and has won multiple awards for co-hosting the weekly Geekscape podcast and for his series of Safe-For-Work satirical pornographic film critiques, “Geekscape After Dark.” He also writes screenplays and, when coerced with sweet, sweet nothings, occasionally acts in such internet series as “Bus Pirates” and “Heads Up with Nar Williams.” A graduate of the UCLA School of Film, Television and Digital Media, William sometimes regrets not pursuing a career in what he refers to as “lawyering” so that he could afford luxuries like food and shoes.
William can be found on both the Xbox Live and Playstation Network as GuyGardner2814, and on Twitter as – surprisingly – WilliamBibbiani.

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