1. Never Been Kissed (1998)
Michael Vartan is a dreamy high-school English teacher inexplicably drawn to Drew Barrymore, an innocent, bright young student in one of his classes. Under any other circumstances, it's Lolita-lite—or at least Don't Stand So Close To Me: The Movie. But Barrymore isn't actually a high-school student, she's a 25-year-old undercover newspaper reporter posing as a high-school student—so, no harm, no foul on the whole being-sexually-attracted-to-your-underage-students thing, right? Right. Barrymore's article comes out, the entire city of Chicago reads it in a montage, and Vartan meets her on a baseball field in order to give 25-year-old Barrymore her "first real kiss," a phrase that can only translate to "with tongue." Let's hear it for sexually stunted adults who find true love with authority figures who have definite pervert tendencies!
2. Serendipity (2001)
If most modern, conventional romantic comedies are torture, Serendipity is the rack. Two of the blandest people in the world (John Cusack and Kate Beckinsale) meet at a department store, reaching for the same bland gift: a pair of black cashmere gloves. They spend a thoroughly bland afternoon together in New York City, during which time they fall head-over-heels into the pools of blandness reflected in each other's eyes. But rather than exchanging names and phone numbers, Beckinsale—whose crippling search for "signs," Cusack inexplicably sees as charm rather than insanity—decides they should write their respective contact info on a $5 bill and an old book, and leave their next meeting up to fate, as represented by used-book sellers and the rotation of U.S. currency. Naturally, the two spend the next five or so years pining for each other. In short, it's an entire movie that could have been avoided if Cusack had merely given the correct response to Beckinsale's let's-leave-it-up-to-fate plan: "Uh, never mind."
Of course, a movie this sappy has to have some rabid fans, including some who make homemade music videos to the accompaniment of Nickelback:
3. Mannequin (1987)
A department-store window-dresser (Andrew McCarthy) falls in love with a mannequin: It's a tale as old as time, right? The twist here is that the mannequin (Kim Cattrall) is actually an ancient Egyptian princess who was transformed into a mannequin thousands of years ago, and the only way the curse can be broken is through true love (or a wood-chipper, whichever comes first). Still, even though she's thousands of years old and a mannequin, Cattrall does have a knack for designing stunning department-store windows—a talent that she uses to fuel the flames of man/ancient-Egyptian-princess-frozen-inside-a-lifeless-doll passion between herself and McCarthy. (The soundtrack by Starship also helps.) Romance with an inanimate object has never seemed so possible.
4. The Night We Never Met (1993)
The unhappily married Annabella Sciorra is in love with one of the men she shares her apartment with. The problem is, she doesn't know the men she shares her apartment with, because it's a blind time-share! Also, one of the men (Matthew Broderick) is sweet, clean, and smart, while the other is a piggish, unkempt jerk (Kevin Andersen). How will she be able to tell which one she wants to have an affair with? The only lesson to be gleaned from this labored comedy is that love and time-share apartments usually don't mix well.
5. 50 First Dates (2004)
Sometimes, goofy ideas for movies turn out less goofy than intended. 50 First Dates stars Adam Sandler as a marine biologist who falls in love with Drew Barrymore, a woman whose short-term memory fades every time she goes to sleep. At first, the movie sets this premise up as the perfect stage for Sandler-esque hijinks: loads of comic misunderstandings and slapstick, slow-burn frustration, plus some gross-out gags and random Rob Schneider sightings. But the escapist trappings of the movie's Hawaiian setting and laid-back covers of '80s hits slam into a wall once screenwriter George Wing and director Peter Segal realize that they don't have a clean way to resolve their romantic leads' problem. What starts as an adolescent dream—getting to relive the moment of falling in love every day, without having to grapple with the inevitable slow fade of romance—becomes a remarkably uncompromising love story about a determined boy-man and a chronically sick woman. Admirable, in a way. But not much fun.
6. Simply Irresistible (1999)
Unlucky in love and her career as a professional chef, Sarah Michelle Gellar gets her life turned upside down thanks to the divine intervention of a Truman Capote-ish fellow (Christopher Durang) and his magic dancing crab, one of whom gifts her with the ability to make emotion-enhancing food. (The gods apparently have a fondness for Like Water For Chocolate.) All that stands between her and true love ('90s semi-star Sean Patrick Flanery) is his stubbornness and her insecurity, both of which prove magic-crab-resistant for nearly 90 minutes, then vanish just in time for the credits. A flatfooted piece of whimsy, the film failed to confirm Gellar as a viable romantic lead or make crabs synonymous with romance.
7. Failure To Launch (2006)
You know what's an awesome, totally reasonable career choice? Fooling overgrown man-children into falling in love with you, thus "building their confidence" enough to inspire them to move out of their parents' houses, then charging the parents for your services. Good ways to do this include tricking the guy into asking you out, staging a beloved pet's death, and fucking him while his parents are asleep down the hall. Yup, it's a foolproof, not-creepy-at-all business model. Unless, of course, your target is that impish, bronzed frat-boy Matthew McConaughey, in which case, Sarah Jessica Parker, prepare for the ironic sting of Cupid's arrow. In Failure To Launch, Parker's best-laid plans go predictably awry, culminating in a kidnapping and forced reconciliation, which the entire secondary cast watches via remote webcam at a nearby café, because that's totally something friends and family would do. Bonus absurd side romance: Parker's irritable roommate Zooey Deschanel falls for McConaughey's nerdy friend after he helps her take out the noisy bird outside her window with a BB gun.
8. How To Lose A Guy In 10 Days (2003)
A nasty battle of wills crowbarred into a romantic comedy, How To Lose A Guy In 10 Days proves that there's no better path to everlasting love than self-serving deception. Inhabiting perhaps the two biggest modern rom-com stereotypes, Plucky Magazine Girl Kate Hudson and Cocky Advertising Guy Matthew McConaughey get trapped in a faux relationship, as she attempts to win him and drive him off within 10 days for an article she's writing, while he simultaneously tries to win a bet that he can make any woman fall in love with him in—you guessed it—10 days. Though McConaughey and Hudson's chemistry and overall likeability obscure the plot's latent malice, the fact remains that they spend the majority of the movie trying to screw each other over.
9. Good Luck Chuck (2007)
Why limit yourself to a single-comedy killing gimmick when you can double up for twice the inanity? That's the thinking behind the risible gross-out romantic comedy Good Luck Chuck, a lowbrow romp that explores what happens when the world's klutziest gal (Jessica Alba) meets a man (Dane Cook) who brings romantic luck to every woman he has sex with. Alba flails her way through a series of awkward pratfalls while the filmmakers strain desperately to eke laughs from Cook's dalliances with a bevy of marriage-minded lookers and a pair of morbidly obese grotesques. Hilarity fails to ensue.
10. Overboard (1987)
In a love story for the ages, grubby contractor Kurt Russell suffers the barbs of uppity rich girl Goldie Hawn before she cheats him out of a paycheck. When Hawn falls off of her yacht and washes up with acute amnesia, Russell comes to her "rescue"—which in this case means kidnapping her, convincing her they're married, and forcing her to look after his three hellions and perform humiliating chores until he gets his revenge. The chemistry between the real-life offscreen couple aside, there's a huge ick factor (not to mention a criminal, morally repellent factor) here: Russell dresses Hawn in his dead wife's clothes, cuts her off from the outside world, and basically rapes her under false pretenses until Stockholm syndrome kicks in and she grows to love him. In fact, swap out Russell and Hawn for Eric Roberts and Tori Spelling, and you've got a great victimization story for Lifetime. (Suggested title: Drowning In Deception).
11. Hello Again (1987)
In the Big Book Of Hollywood Miscalculations, there's a place for Shelley Long's decision to leave Cheers in 1987 to pursue a film career. Cheers became one of the best-loved television shows of all time, and Long's movie career quickly tanked. Hello Again, filmed before her final season on Cheers, makes her choice even more baffling. Long plays Lucy Robinson, who meets an untimely death when she chokes on a chicken ball. After her death, everyone quickly moves on—husband Corbin Bernsen marries Long's friend Sela Ward—except Long's kooky sister Judith Ivey, owner of an occult bookstore. On the one-year anniversary of Long's death, Ivey casts a spell to raise Long from the dead. It works, but with a catch: Long has to find true love within 30 days, or she'll die again. Good thing Gabriel Byrne, the handsome ER doctor who tried to save her, is available.
12. What Women Want (2000)
Mel Gibson plays a womanizing ad man who can suddenly hear women's thoughts. Will it change him? Or will it just help him score with Helen Hunt? The gimmick of suave stud Gibson learning that women secretly fear and loathe him isn't a bad starting point for a romantic comedy, but What Women Want director Nancy Meyers screws up the balance between the two leads, making Gibson a likeable oaf and Hunt a mewling wimp who was apparently talented enough to become Gibson's boss, but is too weak to stand up to him when he starts stealing her ideas. Also, while people probably do think cogent, complete sentences to themselves when they're sitting silently, they probably don't do it while they're in the middle of a conversation. And if they do, they don't react outwardly to the thoughts in their head. At one point, Hunt catches herself looking at Gibson's crotch, and recoils as though she's been punched in the face. If she did that in the real world, she'd be doing the rest of her inexplicable contorting in a sanitarium.
13. He Said, She Said (1991)
After When Harry Met Sally, romantic comedies based on the "Hey, men and women sure are different!" concept were thick on the ground, with a surprising number of them using journalism and/or politics as a hook. In He Said, She Said, Kevin Bacon and Elizabeth Perkins play newspaper columnists (and later television editorialists) who present opposing sides of local issues: the conservative regular-guy side versus the touchy-feely liberal side. They're also lovers who remember the details of their romance differently—a gimmick which directors Ken Kwapis and Marissa Silver convey by telling their story first from Bacon's perspective, then from Perkins'. This is one of those ideas that probably sounded like a winner in the pitch room, but in order to make it work, Kwapis and Silver (and screenwriter Brian Hohlfeld) have to exaggerate the differences between Bacon and Perkins to such a degree that the concept really becomes, "Hey, contrived movie characters sure are different!"
14. 40 Days And 40 Nights (2002)
Josh Hartnett has a problem: After a brutal breakup, he decides to give up sex for Lent, only to fall in love with Shannyn Sossamon during his time off. What's a celibate twentysomething to do? There's a lot that gets in the way of the supposed tension here. First, it expects an audience of schlubs who've probably done 40-day sexless stretches involuntarily plenty of times, and without having to fend off a city full of willing hotties. Then it requires Hartnett to keep quiet about his vow, when chances are that most prospective girlfriends would find it kind of noble, even if there is money riding on it. Finally, it's only Lent. Screw it.