Warner Bros. Pictures
It's one thing to value honesty in a relationship, but it's the absolute worst when you're forced to tell the truth ALL the time (have you seen Liar Liar?). In the film, Mark and Anna's date begins with Anna confessing that she was delayed because she was too busy masturbating. Then, when she takes her call at dinner, she casually explains to her mom (in his presence) that he has a frog-like face and is financially unstable. To top it all off, she also confirms that she won't be sleeping with him or kissing him. We felt so bad for poor Mark! The over-honesty is part of the premise of the movie, but still... it's pretty bad.
Walter thinks he's in for a night of fun when his brother sets him up on a blind date with Nadia - especially when he hears that she gets wild after consuming alcohol. (Not cool NMW, but we digress.) Things go horribly wrong after she starts drinking a little too much. She gets into a ton of mischief and eventually crosses paths with her ex, who then stalks them throughout the entire date and even tries to attack Walter. All the drama causes him to get fired from his job and, at one point, he even gets arrested for causing trouble at a party. We bet he wished he could take that entire day back.
It's kind of insane how far some of us would go to impress a date. In this case, Reuben agrees to try Moroccan food with Polly, even though he clearly has irritable bowel syndrome. Of course, after he forces himself to try the spicy food, things go south pretty fast. He tries to maintain a conversation, even though he's sweating profusely. But it isn't until the stomach noises get super loud that he finally excuses himself. To make matters even worse, the restaurant bathroom's only stall is already occupied.
Just imagine going out with a guy who goes out of his way to make your life a living hell. In the film, Tank actually gets paid to lure girls in and then treat them like trash so they're driven back to their exes. So really, this movie is loaded with horrid first dates. But one of the worst and most offensive that we've seen by far is his date with Rachel. He drove recklessly while totally disregarding her discomfort, felt her up without her consent, and purposely took her to the grossest restaurant in town. If we could crown anyone the king of douchebags, then it would be this guy — but also their exes for submitting those women to such horrors.
What feels like a promising adventure turns into a disaster when Ben tries to sabotage his date with Elaine. Since her mom (aka the lady Ben's been having an affair with) secretly forbids him from getting with her, he drives recklessly, ignores her, and actually takes her to a strip club. It's only when she leaves in tears when he starts to feel guilty and he offers to take her somewhere else. But when they get to the Taft hotel, everyone refers to him as "Mr. Gladstone." Elaine then quickly figures out that he's been having an affair with a married woman (though he claims that it's over). This is definitely not the ideal first date.
Buena Vista Pictures
We still can't get over the fact that a teenaged kid was bold enough to invite his adult teacher out on a date. Fifteen-year-old Max is infatuated with the new first-grade teacher, Rosemary Cross. And for some reason, she simply tolerates his pursuits and accepts his invitation for dinner. When Miss Ross casually invites another guy to join them on their "date," Max is practically livid. He goes from being super rude to her guest to having a complete meltdown over the fact that his date isn't going according to plan. And to top it all off, he admits out loud that he's in love with her. ...So awkward.
20th Century Fox
This sounds like every high school boy's worst nightmare. While preparing to go to prom with his crush Mary, sixteen-year-old Ted Stroehmann ends up getting his scrotum stuck in the zipper of his pants. Oh, and for the record, this all happens while he's in the bathroom of Mary's home. Mary's step-father intervenes and tries to help out, but then Ted starts bleeding once the pants are unzipped. He's quickly wheeled away in a stretcher and taken to the hospital, all while the entire neighborhood watches along...
Before Harry and Sally officially became an item, they thought it would be a good idea to go on a blind double date. They try to set one another up with their best friends, but these conversations turn out to be too awkward and forced. Still, Marie and Jess wind up being attracted to each other and they soon make up an excuse to leave together. Meanwhile, both Harry and Sally are left together after being ditched by their respective dates (who, for the record, eventually get married).
To say that this was a nightmare feels like such an understatement. Jim secretly sets up a webcam so that he and his friends can catch Nadia getting undressed while she changes for ballet class. (Gross, disgusting, pervy, etc.) However, when he joins her later on, he forgets that his webcam is still on and that he sent the webcam link to everyone in his school. As Jim and Nadia try to get physical, it is everything but smooth. Jim basically panics and fumbles through it all...while his classmates watch. Karma's a b*tch.
What made their date so painful to watch is the fact that everyone else could see that Christian is gay... except for Cher. He even flirts with a male bartender right in front of her and she still doesn't catch on (because she's too busy cooing over the fact that he's "ignoring other girls"). In time, though, she notices that Christian doesn't seem to have a romantic interest in her. And that's when it finally sinks in that she's been pursuing a gay guy the entire time.
Well, technically, it doesn't count as real date. Marty was only desperate to make his parents meet because if they didn't, then he'd no longer exist. He came up with a plan to feign inappropriate advances on Lorraine, aka the younger version of his MOM, all so that his future dad, George, would come to her rescue. But things didn't really go according to plan because it was Biff that she needed rescuing from (thank goodness...). Seeing as how his own mother tried to make out with him at one point, we're not sure we'd have been able to bare seeing Marty make inappropriate advances.
This date doesn't even last long enough for us to learn her date's name. But in the opening scene, we hear Kate airing her frustrations about work and the fact that she still doesn't have a child. To top it all off, she then announces that she wants a baby ASAP because she's already getting old. Her date simply stares back at her, at a loss for words. And it's only then that she realizes she shared way too much information.
After admitting that she might've overshared for their first date, the guy quickly excuses himself, as if to go to the restroom. But only seconds later, she looks out the window and spots him running towards a cab so he can leave. Ouch.
Their first date seems to be going okay at first. But when they get to the theater and are about to watch a movie, Hugh tries to point out a girl in a yellow dress to Jamie. Jamie says that there's no one there, but then Hugh insists that there's a girl there. When Jamie confirms that there is, in fact, no one there, he suddenly looks terrified and makes up an excuse for them to leave. Now, if we were in Jamie's shoes, we'd have most likely taken this as our cue to run in the opposite direction.
Sam was understandably reluctant to join in on her BFFs' sex pact because she's a closeted lesbian. But because she wanted to bond with her friends, she agreed anyway and wound up going to prom with a dorky ginger named Chad. Of course, there's literally no chemistry (because one, Sam's way out of his league and two, she's already head over heels for another girl, Angelica). Even so, Sam forces herself to kiss him at one point and she even gives him a handjob while drunk. This entire date just felt like a waste.
We wish so badly that this scene made it into the final cut, but it still counts as one of the worst first dates we've ever seen. As Annie waits for Tyler, his adorable son decides to have a chat with her and it is just beyond awkward. The first question that he asks is "Are you afraid of dying?" Then he goes on to claim that his mom is going to kill her and that his grandma died exactly where she's sitting. It's hilarious, yet extremely creepy at the same time. But fortunately, Annie doesn't have to deal with Tyler's son for much longer. Only moments later, she learns that he's not really over his ex-wife.
Fox Searchlight Pictures
If you put a recently separated woman who values commitment next to a sex addict who avoids serious relationships like the plague, what do you get? A date that's filled with tons of uncomfortable silences and tense conversations. It's not as disturbing or awful as the other dates on this list, but the awkwardness was still so tangible. When Brandon went out with Marianne, he thought it would be a good idea to explain why he doesn't like the idea of being married. That prompted Marianne to ask about his longest relationship. And his response? Only four months. ...Um. RED FLAG.