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- In Look Who's Talking, James sabotages Molly's date with the fellow accountant, telling him not to pay for dinner, open the door for her, etc. Molly's pretty unhappy with both the date and (when she learns of it) James' interference.
- In Along Came Polly, Reuben's date with Polly is ruined because the restaurant she chose triggered his IBS.
- This is pretty much the whole premise of the film Mystery Date. The main character borrows his bother's car for his date and finds a dead body in the trunk.
- Sandy is set up on a Blind Date that turns out to be a disaster in The Rebound.
- In Something New, Kenya and Brian meet on a Blind Date that goes horribly when she realises he is white.
- In Problem Child 2, Junior has a bit of a problem adjusting to his dad trying to get him a new mom, and as a result sabotages two of his dates. This sets up the Cassandra Truth situation later in the movie where Junior is trying to get his dad not to marry Lawanda Dumore, a child-hating Rich Bitch who has it in for him.
- The movie Blind Date is all about Bruce Willis being set up with a woman who shouldn't have alcohol... and yet he lets her drink.
- The entirety of "Once Bitten, Twice Shy", a My Little Pony: Friendship Is Magic fanfic, is built around one of these. Take serious social awkwardness, add very bad advice and minor intoxication, and stir.
- In The First Of Many, Princess Twilight Sparkle is terrified that her first date ever might go like this. Being the Cool Big Bro he is, Shining Armor calms her down by telling his sister the story of his Bad Date, which went so horribly wrong that it warped back to being wonderful again.
- Twilight gets one in A Stitch In Time when she accepts a blind date as petty retaliation after having a row with her current girlfriend, Azalea. The date, Algae Bloom, takes her to a shady bar, repeatedly tries to get her drunk, insults Twilight's intelligence, insults Twilight's current girlfriend, and generally acts like a date rapist. Finally Twilight has enough, gives her a solid "The Reason You Suck" Speech, and walks out to reconnect with Azalea. She also informs Cloudkicker (who is promiscuous but has solid dating ethics) about the ordeal and asks her to spread the word so Algae Bloom won't prey on anypony else.
- The aptly-named anthology Dates From Hell by Katherine Salmon is a collection of these. Supposed to be comedic, but sometimes they cross the line: it opens with a (fictional) story in which the protagonist steps on the neck of her boyfriend's mother's dog, snapping it.
Live Action TV
- On How I Met Your Mother, Ted often goes on dates that go badly. Barney is the quintessential Bad Date.
- Most of the entertainment value of Millionaire Matchmaker comes from this trope.
- On Donna and Eric's first date in That '70s Show, Donna orders an iced tea and is mistakenly served a Long Island iced tea. Not only is the date spent trying to keep Donna from making an idiot of herself, but Hyde later shows up to profess his feelings for Donna.
- There's a one-off episode of Rik Mayall Presents in which Mayall's character manages to give his blind-date the impression that he's a serial rapist and killer, and her panic escalates to the point where she locks him in her burning flat.
- On the Reality TV show Blind Date, dates that went particularly badly were featured as "Dates From Hell".
- Ryan plans a romantic date on Oddities. Dinner and then a meeting with a bone artist and his flesh eating beetles. What could possibly go wrong?
- Star Trek: Deep Space Nine:
- Averted in "For The Cause". The entire B-plot of the episode consists of a build-up that looks like it's going to be a disaster. Shortly after Ziyal first arrives on the station, she and resident spymaster Garak take notice of each other and she ends up asking him out on a date. Bashir points out she's the daughter of Garak's Arch-Enemy, Dukat. Kira threatens Garak's life if he does anything to hurt her. Garak himself is convinced that Ziyal invited him out to kill him on her father's behalf. Quark makes things worse by making Garak believe Kira's in on the plot as well. Cue the date: Garak takes a gun to the date, Ziyal gives him "The Reason You Suck" Speech.... which clears the air, allowing them to have a good time and get on well with each other.
- Played straight in the "Life Support" B-plot. Jake is overjoyed when the girl of his dreams asks him out on a date. Nog invites himself along and even convinces Jake to convince his date to bring a date along for Nog. Nog trying to treat his date as if she's a Ferengi female. Jake's attempt to keep the peace makes his date think he's siding with Nog. Not only is the date a disaster but it almost ruins Jake and Nog's friendship as well... and it turns out Nog was actually holding back on his behaviour out of consideration for the fact his date wasn't Ferengi; he didn't insist she engage in the full range of activities a Ferengi female would be expected to perform (such as softening his food by chewing it, he thought merely insisting she cut his food for him was a huge compromise).
- Star Trek: Voyager. In "Someone To Watch Over Me", Raised by Orcs Ice Queen Seven of Nine decides to try romantic interactions, but her first date leaves a lot to be desired. She and the hapless Lt. Chapman are both nervous, leading to a string of dinnertime disasters — Seven splitting a lobster with such ferocity that she splats Chapman in the face with it, and ballroom dancing with enough fervor to break his arm.
- JAG: Bud shows up too late at his date with Harriet in "Washington Holiday" because his car had a flat tire.
- On New Girl, Jess asks Nick to give her number to the cute guy she met at his bar. She meant Andy. She ended up with Bear Claw... Andy's chubby, incredibly awkward, doofy co-worker who can't wait to see her meatbar (Damn you, autocorrect).
- The first season of Scrubs had Dr. Cox have unrequited romantic feelings for Carla. A later episode has both Dr. Cox and Carla, separately, talk about the worst date they have ever had. Turk overhears both of them talking and is horrified to learn that they are talking a date they went on with each other years before.
- This happens fairly often to Jon in Garfield, until a storyline of comics from 2006 allowed him and Liz to become an official couple.
- In all of Jonathan Rand's Check Please short plays, most of the comedy is derived from the hilariously terrible blind dates that the two leads, named in the scripts as Guy and Girl, go on before Guy proposes to Girl at the end of Check Please, Take 3.
- The "Trouble Date" episode of Dick Figures is about Blue's date going terribly wrong, thanks to interference from Red.
- Moist has one in Dr. Horrible's Sing-Along Blog.
Dr. Horrible: Hey, didn't you ah... didn't you go on a date last night? Conflict Diamond told me you were doubling with Bait and Switch.Moist: Yeah...Dr. Horrible: Yeah?Moist: It was alright... I kinda thought I was supposed to end up with Bait, but...Dr. Horrible: I hear ya.
- Saturday Morning Breakfast Cereal has a sketch called "Dating Solutions." They also have "Date Wars," which is a bad date summarized in an actiony death-ray battle.
- Statistical Fact: Early signs of a bad date occur when this couple encounters a sidewalk loogie.
Anime And Manga
- Gaia's first date in Fearless ends with her date trying to kill her. She notes that among the worst first date stories she's ever heard, it ranks by and large as the worst she can imagine.
Live Action TV
- In Crossing Kevin's Crossing, on Carly Hawkins and Matthew Myers's date to celebrate their two month anniversary Carly dies from anaphylactic shock after eating a a peanut butter and jelly sandwich.
Both Comedy and Drama:
Anime And Manga
- My Daddy Long Legs has three-couple group date that goes wrong in so many ways in episode 31. The interactions between Bob and Sally are played purely for comedy, but the tension between Jimmie, Judy, and Jervis is pretty dramatic, and it has considerable significance with regard to the emerging Romance Arc.
- In Hitch, he goes on a jet ski date and accidentally kicks her in the face, then accidentally forces her to confront the reality of her genocidal ancestor, and on another date has a bad reaction to food and looks like an ass and... these are funny, but they also demonstrate that he's not actually any good at dating, in spite of his alleged expertise.
- In When Harry Met Sally..., the titular characters bond over bad dating experiences. These are usually comedic, but venture into the dramatic when Harry talks about dates being ruined when he is reminded of his ex-wife and becomes overcome with regret over her.
Live Action TV
- Happens in Burn Notice: occasionally Fiona pushes Michael to treat their relationship like a personal relationship rather than a professional spy relationship with sex involved. One time he promises her a romantic dinner. Unfortunately, after a job goes south, they don't have the money for a nice place, so they end up back at The Carlito, their usual hangout. They play it for laughs and show the rocky nature of Michael and Fi's relationship.
Fiona: I distinctly recall you saying someplace nice. We're at the Carlito; we eat half our meals here. Have you forgotten what a date is?Michael: I said that when I thought we were gonna be five grand richer!Waitress: Would you like anything else?Fiona: Yes, your most expensive dessert, please.A little shop talk, and then Sam sits down.Sam: Well, you two look as good as I feel.Fiona: You invited him?Sam: I need an invite to Carlito's now?A little more shop talk, then Fi's dessert shows up.Sam: Okay, wait a second, is this a date?Michael: Yes. [and at the same time]Fiona: No. This is officially not a date.Sam: Alrighty, can you bring us another spoon?
- On an episode of Friends, Joey and Phoebe purposely set up Ross and Rachel on these to try and get them back together.