clueless, date, alicia silverstone, cher, christian, Justin Walker

Check, Please: 10 Famous Movie Dates You Don’t Want To Be On

You’ve never been on dates this bad. Okay, maybe you have. But unless you’re also a successful screenwriter, those bad dates didn’t end up acted out on the big screen. Count your blessings that you weren’t in on these. (Note to reader: Spoilers will be delivered. All of them.)

After Hours – 1985

Does it count as a date if it’s really casual and lasts all night and one person commits suicide? Sure it does! In Martin Scorsese’s black comedy, Griffin Dunne goes to Rosanna Arquette’s apartment to visit her, finds art photography that suggests she might be disfigured under her clothes, then abandons his romantic plans because that’s how sexually shallow men really are.

Her subsequent suicide is only the beginning of his night-long trip into weirdness, one that results in his being encased in plaster. He kind of deserves it.

Baby Mama – 2008

Who has time to waste? Not you. Lay your cards on the table first thing. See how it goes. “I want a baby now. I’m 37,” says Tina Fey in the opening moments of this surrogacy comedy co-starring Amy Poehler. Her unnamed first date excuses himself from the table and never returns. Finally, she can eat that meal in peace and go have a baby with Poehler. Win-win.

Bad Boys II – 2003

This scene doesn’t technically count as a date. It’s more of a pre-game in which Martin Lawrence and Will Smith terrorize the 15-year-old boy who comes to pick up Lawrence’s daughter for what seems to be an innocent first time out.

The men use abusive, profane language and wave a gun in the kid’s face because apparently it’s funny to be cruel to kids. The boy, for his part, remains stoic and unmoved, which means he’s got bigger balls than either of them. You’ll find yourself rooting for the teen couple to lose their mutual virginity, if only to spite the middle-aged “bad boys.”

(NOTE: The clip above is not a date scene. It’s merely every swear word from the movie shouted out loudly. You’re welcome?)

Freddy Got Fingered – 2001

Professional non-sequitur Tom Green finds a lovely young woman (Marisa Coughlin) to go on a date with him. Her hobbies involve oral sex and having her legs caned hard with a stick, which Green obliges. Green takes her to a restaurant and goes berserk. staging a fake phone call where he screams about money (“You’re fucking fired, Bob!”). Then he tears into his dinner like a wild animal. Green’s father (Rip Torn), eating at the same restaurant, approaches the table to tell him to knock it off, only to have his son tell Coughlan that his father’s name is “Little Timmy.”

There is no rational explanation for this scene or any other scene in this film, for that matter. It’s a piece of bizarro cinema that one must live in order to understand. And even then you will not.

The Cable Guy – 1996

Jim Carrey and Matthew Broderick go on a man-date to Medieval Times. Ever been to one of those? No? Dude, THERE IS FALCONING AND JOUSTING. Stop reading this article and go to a Medieval Times right now. Anyway, while eating chicken on their date they dare ask “serving wench” Janeane Garofalo for silverware, to which she responds, “There were no utensils in medieval times, hence there are no utensils at Medieval Times. Would you like a refill on that Pepsi?” The evening ends in a duel and builds the foundation for Carrey’s slow-burn obsession with Broderick, as all good same-sex romances do.

clueless, date, alicia silverstone, cher, christian, Justin Walker

Clueless – 1995

Poor Alicia Silverstone. All dressed up on a date with a gay boy and she doesn’t even know it, her best moves lost on the oblivious Christian (Justin Walker, who sort of disappeared after this one). Perhaps his film selections of Some Like It Hot and Spartacus should’ve been a clue. Whatever, she winds up with her hot, ex-stepbrother Paul Rudd anyway.

Happiness – 1998

In Todd Solondz’ comedy of emotionally stunted human manners, extremely-lonely-nerd-slash-depressed masturbator Philip Seymour Hoffman takes Camryn Manheim out to eat. There, she confesses to dismembering a man who attempted to rape her. She confesses that she hates sex, then she asks if they can be friends.  “Um… I guess, yeah,” Hoffman replies. “I mean, we all have our… you know… our plusses and our minuses.” This is as sweet at it ever gets in Solondz’s world.

Harold and Maude – 1971

Harold (Bud Cort) is a young, death-obsessed man who finds himself attracted to 80-year-old Maude (Ruth Gordon). They fall in love, but not before Harold’s mother sets him up with three “age appropriate” girls. Date number one: Harold fakes setting himself on fire. Date number two: Harold fakes chopping off his own hand. Date number three: The girl stabs herself. Sure, there are less extreme ways of rebelling against parental meddling, but most of them don’t measure up to this level of ingenuity.

Rushmore – 1998

Private school teacher Olivia Williams has a problem. She’s on a dinner date with three men at the same time: grumpy Bill Murray, doctor Luke Wilson, and self-possessed Jason Schwartzman, who is also her wildly overachieving student and a resolute smart-ass. The entire scene builds to this classic burn:

Schwartzman, to Wilson: I like your nurse’s uniform, guy.

Wilson: These are O.R. scrubs.

Schwartzman: O, R they?

Then, after sipping on more whiskey and soda, the increasingly aggressive Schwartzman declares to Williams that he loves her. This, teens, is how you go for it.

Taxi Driver – 1976

Cybill Shepherd goes on a date with Robert De Niro. Such a handsome couple. Except he’s suffering from a little light mental illness and takes her to a porn theater. No second date for Bob.