The 25 Worst Dates in Movies

We've all had our fair share of bad dates. But when it comes to the worst of 'em, few places beat Hollywood. Yes, that golden city by the sea that's made an industry out of happy endings has a bit of a masochistic side, too. Especially when it comes to its portrayals of the dating scene.

From sex addiction to pedophilia, from deviant acts to murder, here are The 25 Worst Dates in Movies.

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Interview by Jennifer M. Wood (@j_m_wood)

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Tina Fey has perfected the single-aging-woman-who-wants-a-baby-routine. It was a staple of her Liz Lemon character on 30 Rock and is the main plot point of this rom-com, in which aging professional Kate Holbrook (Fey) hires a South Philly chick (Amy Poehler) to be her surrogate. It's really no wonder why Kate can't find a father for her would-be child.

On a blind date, she thinks it's best to get right to the point, telling her would-be suitor: "I'm 37 and I want a baby!" He quickly excuses himself, hightailing it out the door and flagging down the nearest cab.

After Harry (Billy Crystal) met Sally (Meg Ryan), but before they'd got serious and married, the titular couple tried setting each other up on a blind, double-date: Harry with Marie (Carrie Fisher) and Sally with Jess (Bruno Kirby). But Marie and Jess only have eyes for each other.

Minutes after separately promising their friends that they'd spare everyone's feelings and not act on their attraction that night, they find an excuse to share a cab home, leaving Harry and Sally in the dust.

California girl Cher Horowitz (Alicia Silverstone) is young, rich, beautiful, and looking to get her claws into Christian (Justin Walker), the new guy at school. Charmed by his regular onslaught of compliments on her sartorial choices, Cher puts on her sexiest dress and invites him over for a night of movie-watching (and then some).

But she quickly discovers that her friends were right when they told her that Christian is "a disco-dancing, Oscar Wilde-reading, Streisand ticket-holding friend of Dorothy." (Translation: He's gay.)

As if going out with your ex-sister-in-law wasn't awkward enough, Mickey (Woody Allen) and Holly (Dianne Wiest) quickly discover that, even though they've known each other for a while, they have nothing in common. She's a floundering former addict who likes to party. He's a straight-laced hypochondriac who likes to whine.

But all turns out well in the end; after a disastrous first date (which Mickey describes as "like the Nuremberg Trial") the two reconnect and eventually marry.

It's got all the makings of a blossoming romance: After casual flirtations in the office, co-workers Brandon (Michael Fassbender) and Marianne (Nicole Beharie) decide to make an official date. He shows up late (he stopped to watch a couple have sex through a hotel window) and all that office banter comes to a screeching halt when they realize they don't know what to say to each other.

Marianne, recently separated, expresses her hope for finding a lasting relationship. Brandon, a sex addict, has never had a relationship last longer than four months. Despite the awkwardness, Marianne allows him to whisk her away for an afternoon quickie the next day during work. Except Brandon's having trouble getting his equipment to work, so Marianne leaves.

Moments later, we see him having sex with another woman in the same hotel room. Pity those kids couldn't work it out.

We're all for honesty in a relationship, but the total lack of any sort of fibbing can be, well, disconcerting. Writer Mark Bellison (Ricky Gervais) learns this lesson the hard way on his first date with Anna McDoogles (Jennifer Garner).

Upon his arrival, Anna informs Mark that she was late answering the door because she was busy masturbating. And later informs him—quite sweetly—that his looks and sad state of financial status make him very unattractive to her. She does not want to have short fat kids with snub noses.

There are few lengths of humiliation to which Ben Stiller won't go for a laugh. In Along Came Polly, he's a risk-averse risk assessment specialist who has reconnected with Polly Prince (Jennifer Aniston), a free-spirited friend from junior high school. Not wanting to kill the mood on their first date, Reuben agrees to have dinner at a Moroccan restaurant, even though he can't eat spicy food.

It's not difficult to imagine the many well-worn movie tropes that follow; let the profuse sweating, frantic water-drinking, bodily noises, loud bathroom scenes and overflown toilets ensue!

Being forced to take your sister to the prom for lack of any other options is one thing. But taking your mom to her own prom so that she and your dad can fall in love, get married ,and ensure your future existence? That's something you'll likely only ever find in this '80s classic, where teenage time traveler Marty McFly (Michael J. Fox) is forced to rewrite the history of his parents' (Lea Thompson, Crispin Glover) high school romance.

The only problem? His mom's kind of into him. But all works out when Marty escorts his mama to the Enchantment Under the Sea dance; not only does he save the day—and his own life—but he gets the chance to introduce the world to rock 'n' roll.

The five-mile stretch between SoHo and Manhattan's Upper East Side becomes a vast wasteland of insurmountable obstacles in the hands of Martin Scorsese, as straight-laced word processor Paul Hackett (Griffin Dunne) tries to make his way uptown after a would-be date with Marcy Franklin (Rosanna Arquette) turns disastrous. (He learns that she has a boyfriend and has committed suicide.)

Burglary, mistaken identity, an empty wallet, and a ruthless mob of downtowners are just a few of the other things that stand between Paul and his own bed.

The surest recipe for a bad date? When one party doesn't know the meeting is intended to be a romantic one. Marge Gunderson (Frances McDormand) has to break the news to former high school classmate Mike Yanagita (Steve Park) that she did indeed marry ol' Norm "Son of A" Gunderson. And that she's about to deliver their first child. Which means she's completely off the market. No, really.

Crying ensues.

Recent college grad Benjamin Braddock (Dustin Hoffman) has gotten himself into a bit of a pickle. After revving up the engines on an illicit affair with Mrs. Robinson (Anne Bancroft), the very married wife of his dad's business partner, he is encouraged to go on a date with Elaine (Katharine Ross), Mrs. Robinson's beautiful, more-age-appropriate daughter.

Though Benjamin finds himself falling for the younger Robinson, he's promised her mom that he'll be on his worst behavior. Which in this case includes alternating between ignoring and insulting Elaine, and then capping off the evening with front row seats at a strip club. Good times!

It's all fun and games until someone ODs. Though not a "date" in the traditional sense, Mia Wallace's (Uma Thurman) night out with thug Vincent Vega (John Travolta) is indeed the kind of which nightmares are made.

It all starts off innocently enough, with the two engaging in the kind of rapid-fire dialogue that has made Quentin Tarantino a household name. They even partake in a dance contest that sees Travolta putting his Saturday Night Fever shoes on. But when Mia mistakes some heroin for coke and snorts a lot of it, the good times come to a screeching halt. The evening ends with Vega administering a shot of adrenaline directly to her heart.

Thirty-something photographer Jeff Kohlver (Patrick Wilson) clearly has not been keeping up with To Catch a Predator. If he had, he'd clearly know that trolling the Internet for underage-but-willing girls can only end in disaster.

But Chris Hansen's got nothing on Hayley Stark (Ellen Page), the object of Kohlver's affection who turns the predator into the prey once she gets him alone at his apartment. The torturous teen will stop at nothing to get Jeff to admit to his deviant ways—and it works.

The title of British indie says it all: A sexy spin on a luxurious yacht in Mallorca, Spain, turns into not such a good time when Josh (Julian Morris) and Lisa (Sian Breckin)—being videotaped—engage in the titular sexual act, with fatal results.

While the female members of this party want to report the incident to the authorities, Josh and his friends decide to throw Lisa's body overboard. The night takes an even more disastrous (and even deadlier) turn as the two genders fight over how to proceed, both of them angling for the videotape that will explain it all.

Going out to dinner as a foursome is nothing new. But when you're the sole female (Olivia Williams) at a table with three men (Bill Murray, Jason Schwartzman, and Luke Wilson)—all of whom have romance on the brain—things are bound to get awkward. Especially when one of your suitors is an overachieving teen who professes his love right then and there, but not before offering the film's best exchange:

Max: I like your nurse's uniform,guy.

Dr. Flynn: These are O.R. scrubs.

Max: O, R they?

Dead.

Master of horror Wes Craven knew it would take a lot to outdo the opening of the original film in the Scream, so he went for the gut—literally—in the first few minutes of that film's sequel.

All starts out pleasantly enough, as college co-eds Phil Stevens (Omar Epps) and Maureen Evans (Jada Pinkett, before -Smith) attend an opening night screening of Stab, a movie based on the "real-life" events of the film's first events. Yes, things get meta. And they don't end well for either half of this doomed duo, whose names bear a striking similarity to the players in the first film and, as such, become part of the carnage.

Phil goes down first, when he hears a strange noise in the men's room stall and presses his ear to the divider to get a better listen. (Big mistake.) Maureen is next, when the costumed killer returns to Phil's seat, where he stabs her to death in front of an excitable crowd who believe she's just part of a super-cool publicity stunt.

Wall Street warrior/serial killer Patrick Bateman (Christian Bale) may be hot. But when the best a girl can hope for from a date with him is to emerge alive, it's probably best to keep looking for a more suitable mate.

Mary Harron's adaptation of Bret Easton Ellis' classic Reagan-era novel is chock full of one bad date after the next: there's Evelyn (Reese Witherspoon), Patrick's pseudo-girlfriend, too wrapped up in her socialite status to see what Patrick really is; Jean (Chloe Sevigny, pictured above), Patrick's personal assistant who is clearly—and blindly—infatuated with him; Courtney (Samantha Mathis), the debutante and other woman too hopped up on prescription meds to remain conscious through a single dinner; and Christie (Cara Seymour), poor Christie, the sad-sack prostitute who, after a frightful threesome that lands her in the hospital, returns for a second round of sexual abuse, only to be cut in two with a chainsaw.

The '80s sucked.

Leave it to Eastbound & Down creator Jody Hill to play date rape for laughs. Mall cop Ronnie Barnhardt (Seth Rogen) thinks he's hit the jackpot when makeup counter hottie Brandi (Anna Faris) agrees to have dinner with him. In between tequila shots, she pops a couple of Ronnie's Klonopin, rendering her barely conscious by evening's end. But Brandi's lack of mindfulness nor the fact that she's covered in vomit prevent Ronnie from seeing this date conclude the way he hoped it might: under the covers.

Hill softens the blow by having Brandi wake up during the act and urge Ronnie to keep going, implying that she was conscious for the start. Whether Hill's "softening" of the joke bothered you or not says volumes about whether or not we'll hang out with you.

Meddlesome moms never make for great matchmakers. Following his release from prison after exposing himself to a minor, convicted sex offender Ronnie McGorvey's (Jackie Earle Haley) mom decides a date is just what he needs. So she fixes him up with Sheila (Jane Adams), a young woman with a tortured past of her own.

They open up to each other over dinner, but Ronnie clearly gets too comfortable too quickly. On the way home he asks her to stop at the local playground... where he proceeds to masturbate while watching some young girls at play. It's just as horrible as it sounds.

Any delusions of getting some on prom night are dashed the moment Ted Stroehmann (Ben Stiller) jams his junk in his zipper in the bathroom of dream girl Mary Jensen's (Cameron Diaz) house. To make matters worse, Mary's stepdad (Keith David) takes it upon himself to try and remedy the situation, only to question, "How'd you get the beans above the frank?"

All of the neighborhood watches on as an ambulance ride to the hospital replaces a limo to the big dance for Ted.

To reiterate, Ted caught his penis and scrotum in the teeth of a zipper.

New York City cabbie Travis Bickle (Robert De Niro) has a way with women... And by that, we mean a way to ensure that a second date will never be in the cards.

After somehow cajoling Betsy (Cybill Shepherd), a beautiful young political volunteer, to go out with him, he attempts to woo her by taking her to see Language of Love, a Swedish sex film. Betsy is horrified, Travis is confused as to why. Needless to say, there's no kiss goodnight in this couple's future.

Lesson learned: Movies make for lame dates.