The 15 Creepiest, Worst & Most Questionable Movie Date Nights, Ever

Photo: Courtesy of Zoetrope Studios.
In The Overnight, Taylor Schilling and Adam Scott play a straight-laced suburban couple named Emily and Alex who find themselves at a dinner party/ double date with married (and sexually adventurous) duo Kurt (Jason Schwartzman) and Charlotte (Judith Godrèche). Yes, hilarity ensues — but this particular film goes for way more than just laughs.

Written and directed by Patrick Brice, the sex comedy (yes: that’s “sex comedy,” not “sexy comedy” — although it is kind of sexy), sees Kurt and Charlotte lead Alex and Emily down the road of sexual liberation, as the four characters begin testing the waters of personal and marital comfort zones, relationship boundaries, and the limits of adult friendships. (There's even a Schwartzman/Scott full-frontal-nudity scene included.)

While the movie is interesting, relatable, and well done, not everyone would react well to a freewheeling night at Kurt and Charlotte’s. That’s what made us think about some of the less thought-provoking (and downright horrifying) date nights we’ve seen on the silver screen — ones that don’t probe us to question who we are, but rather leave us reaching for the fast-forward button. Click through to relive them all.

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Video: Courtesy of YouTube.
Movie: Along Came Polly

Date premise: Dinner at an Indian restaurant

What went wrong: Some of us (hello) can’t eat spicy food. Unfortunately, in an attempt to impress Polly Prince (Jennifer Aniston), Reuben Feffer (Ben Stiller) fails to share that particular fact and indulges in an Indian meal that his IBS isn't ready for. The good news: we’ve all been there. The bad: Polly hasn’t, and doesn’t get the hint when Reuben starts sweating profusely and eventually has to use her facilities — which, of course, goes horribly awry. (Again, we’ve all been there.)
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Movie: There’s Something About Mary

Date premise: Prom

What went wrong: If Ted (Ben Stiller) hadn't used the bathroom (always with the bathroom), he would’ve avoided a zipper-based accident and could’ve taken Mary (Cameron Diaz) to prom. Unfortunately, life is difficult, and instead of spending the night on the dance floor, he spends it in the E.R., where doctors eventually extract his penis from the fly of his pants. But not before Mary, her family, friends, and the firefighters draw attention to his personal (and I mean very personal) crisis.
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Video: Courtesy of YouTube.
Movie: Pulp Fiction

Date premise: Dancing, burgers, and the liberal use of a controlled substance

What went wrong: Granted, not much can go right when the guy (John Travolta) assigned to watch the boss’ wife (Uma Thurman) ends up watching her snort heroin to the point of nearly dying. And while the two enjoy dinner, dancing, and enough flirting to call their night out a date, all romance is lost when he has to stab her in the heart with adrenaline to make it start beating again.
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Movie: American Psycho

Date premise: Dinner, drinks, and attempted murder via nail gun

What went wrong: On top of being engaged (to Reese Witherspoon’s Evelyn), Patrick Bateman’s (Christian Bale) fantasies of killing women almost get too real when he invites his secretary Jean (Chloë Sevigny) over and holds a nail gun to the back of her head. Fortunately for her, he doesn’t shoot. Unfortunately for him, Jean finds his notebook filled with rape and murder fantasies, and when Bateman tries to confess to his murderous tendencies, nobody believes him.
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Video: Courtesy of YouTube.
Movie: Scream 2

Date premise: A night at the movies (with a serial killer)

What went wrong: Movies about murder are ideal date material, until an actual murderer uses the screams of an audience to mask his real-life killing spree. Such was the case in Scream 2 when Maureen Evans (Jada Pinkett Smith) and Phil Stevens (Omar Epps) are stabbed to death by the serial killer at a screening of Stab, a movie loosely based on the original Scream. Naturally, nobody notices until the murders are long since completed. (Which easily makes this the worst date, ever.)
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Video: Courtesy of YouTube.
Movie: Back to the Future

Date premise: Prom

What went wrong: Few things ruin a date like your mom showing up, but Marty McFly (Michael J. Fox) has no choice. While trying to reunite his parents decades before his birth (to cement his own existence), he finds himself the object of his mother’s (Lea Thompson) affections, and at one point she kisses him, forever inspiring the grimace emoji.
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Movie: The DUFF

Date premise: Ordering in, sitting outside

What went wrong: Bianca Piper (Mae Whitman) spends weeks psyching herself up for a date with dream-boy Toby Tucker (Nick Eversman) — only to realize he’s been using her just to get close to her friends. After outing him as a liar (upon discovering he lied about having made their sushi dinner himself), she catches him asking about her pals, which eventually prompts him to admit he was never really into her. (Go back inside, Toby.)
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Video: Courtesy of YouTube.
Movie: Little Children

Date premise: A blind date at a restaurant

What went wrong: Frankly, it's a date doomed for disaster. Hoping her pedophile son can start anew, his mother sets him (Jackie Earle Haley) up with a woman named Sheila (Jane Adams), whose past is just as upsetting (but for different reasons). The two bond briefly, but the date ends on an incredibly upsetting note, when he ends up masturbating at a playground. It is the actual worst (but brilliantly acted).
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Video: Courtesy of YouTube.
Movie: Fargo

Date premise: A high school reunion and misunderstanding

What went wrong: A very pregnant Maggie (Frances McDormand) thinks she's just catching up with a high school friend named Mike Yanagita (Steve Park) until he reveals the cold, hard truth: as far as he's concerned, this is a date. Finding out how wrong he is proves so disappointing that he begins crying loudly and openly in the restaurant. The thirst is real.
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Video: Courtesy of IMBD.
Movie: Burn After Reading

Date premise: Your basic blind date (and then some)

What went wrong: When Linda’s (Frances McDormand) blind date turns out to be married (ugh), she becomes even more determined to battle age with plastic surgery, talking openly about her plans for change at work. That grabs the attention of Ted (Richard Jenkins), who tries (and fails constantly) to confess his feelings for her. Sadly for him, his desire to stand up for himself and impress Linda goes even more awry when he eventually gets killed by the man Linda is trying to blackmail. Because this is what happens when you try dating in a Coen brothers movie.
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Movie: Young Adult

Date premise: Rock show at a townie bar

What went wrong:
It would be an ideal date for former high school sweethearts Mavis Slade (Charlize Theron) and Buddy Slade (Patrick Wilson), who spend the night watching a rock band, getting drunk, then kissing on Buddy’s front step. However, with the rock band being that of Buddy’s wife (Elizabeth Reaser), the night has its limitations — especially when the babysitter turns the porch lights on and exposes Buddy for the two-timer he is.
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Video: Courtesy of YouTube.
Movie: Grease

Date premise: Night at the drive-in

What went wrong: After Sandy (Olivia Newton-John) and Danny (John Travolta) are reunited at Rydell High following their summer of l-o-v-e, the two head out on a date to the drive-in, where Danny forgets what consent means. Despite Sandy rejecting his advances, he gropes her, pushes her down, and then leaves her crying after she escapes his car. In response, Sandy effectively dubs Danny’s car the “Sin Wagon” and inspires the Dixie Chicks 20 years before their time. Hell hath no fury, FYI.
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Video: Courtesy of YouTube.
Movie: The 40-Year-Old Virgin

Date premise: Speed dating

What went wrong: After getting tricked into Date-A-Palooza (a speed dating service), Andy (Steve Carell) finds himself in the midst of a few worst-case scenarios (like being asked about his mental capacity). Stay for the celebrity cameos (hello, Mindy Kaling!), and leave for the complete lack of human connection. Four dating nightmares for the price of one.
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Video: Courtesy of YouTube.
Movie: Knocked Up

Date premise: Dinner and a pregnancy announcement

What went wrong: Considering the first night Ben (Seth Rogan) and Alison (Katherine Heigl) met, they hit it off (and had unprotected sex), you’d think a night out in a fancier setting would go a little bit better. It doesn’t. After failing to connect on any level (and with Ben thinking this is a drawn-out booty call), Alison tells him that she’s pregnant. Not with emotion, but with his child. And while this date is painful to watch, the rest is history.
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Video: Courtesy of YouTube.
Movie: Pretty Woman

Date premise: Afternoon at the horse races

What went wrong: Well, what didn’t? On top of Vivian Ward (Julia Roberts) being shamed by the film’s characters for her sex work, she finds herself on several dates with her client, Edward Lewis (Richard Gere), who consistently reminds her of her place in their relationship. That tendency comes to a head when he tells everybody at a horse race who Vivian is and what she does — and it gets worse when his friend (Jason Alexander) tries to sexually assault her, thinking he’s entitled to it. (Bonus points: Edward eventually punches him in the face. Let’s just hope Vivian went on to know she could totally do better than Richard.)
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