Tails: How? By putting me in more danger?
Sonic: The plan had holes!
A situational trope. One character will develop a plan designed to solve a certain problem they're encountering. However, due to their failure to plan ahead, there is a massive gaping flaw in their plan that they—and perhaps the audience—missed. As a result, they are now in a situation where, rather than winning, they are stuck with either a stalemate or an outright loss. Sometimes this may occur because the character never thought that their plan would actually progress as far as it did in the first place.
A more comedic, simple version of Didn't See That Coming. See also And Then What?, when the flaw is not knowing what to do if the plan succeeds. (Also an issue for Who Will Bell the Cat?.) If the person pointing this out is sufficiently annoyed, this can lead to What Were You Thinking?. May also lead to a This Is Gonna Suck or an Oh, Crap! for the schemer when he realizes how screwed he really is. Compare Should Have Thought of That Before X, It Seemed Like a Good Idea at the Time and Missing Steps Plan.
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- The Lamput episode "Houdini" has the docs coming up with plans to catch Lamput that all fall flat. First, they trap him in a cage, but Lamput is small enough to pass through the gaps in the cage. Then, they lock him in a chest, only for Lamput to morph into a key to free himself. After that they stuff him into a big sack, but Lamput shapeshifts into a pair of scissors and cuts through the sack. It's only when they trap Lamput in a big jar that the docs finally have him... but even then Lamput seemingly dies of suffocation due to the jar lacking air holes, only for him to turn out fine once he's out of the jar.
- 1973's The Watergate Comedy Hour starts with President Nixon doing a press conference à la The Tonight Show. When a reporter gets too close for comfort asking about the Watergate break-in, Nixon confers with his second banana, "Doc" Kissinger:
Nixon: Doc...Doc...it looks like I'm up against it. What do we do?
Doc: Well, Mein Herr, it looks like we need a fall guy.
Nixon: But I've used up so many already.
Doc: We need someone in the public interest. Someone close to you, yet someone they would never suspect.
Nixon: Yes, but who?
Doc: Your wife Pat.
Nixon: My wife Pat?! You can't be serious. You don't think for a moment that I would ever entertain the thought of sacrificing someone near and dear to me for the sake of political expediency. No, no. There must be someone else.
Doc: Only you.
Nixon: [after a beat] Uh, it can now be revealed that my wife Pat conceived and led the Watergate affair. I am truly shocked and saddened. Of course, I had no prior knowledge of this illegal act—for you see, Pat and I have never spoken.
- Two drunks are fishing when one drags up a Genie in a Bottle, who is ready to grant him one wish. He wishes for the ocean to turn into beer, which is granted. As he looks ecstatically at his companion, he gets slapped upside the head and is told: "You idiot, now we have to piss in the boat!"
- Have you heard the story of Bottleneck Bob? He tried to rob the train with cattle, but evidently forgot they needed to be corralled somehow: "The cattle ran all over the place/And there was Bob with the longest face..."
- In Eminem's "Stan", the title character, furious that his idol Eminem still hasn't responded to any of his letters, is about to drive off a bridge with his pregnant girlfriend locked in the trunk of his car and drown them all, and is narrating these events into a tape recorder as a final letter to Eminem. The obvious flaw in his plan — namely, that he can't mail the tape to Eminem if he's dead — doesn't occur to him until just as he's going over the edge.
Well, gotta go, I'm almost at the bridge now.
Oh, shit! I forgot! How am I supposed to send this shit out?!
- In the Mozart opera The Abduction from the Seraglio, the hero Belmonte gets captured by the Pasha, who already holds his betrothed Constanza captive. He says that his father can pay a generous ransom for them, only to be informed that said father is a mortal enemy of the Pasha. Oops.
- Kids Praise: The seventh album begins with two separate instances of this trope in action:
- First, Psalty agreed to a history-of-hymns project that would take weeks of research, and would be due in two days. He even admits that he agreed without realizing how long it would take.
- Second, he tries to invent a machine that stretches time to allow himself and the kids to do those weeks of research in under 24 hours. However, he shows it to the kids before he tests it, and kids will be kids..
- The children's song There Was an Old Lady Who Swallowed a Fly. She keeps swallowing creatures to catch the last thing she swallowed.
She swallowed the cow to catch the goat, she swallowed the goat to catch the dog, she swallowed the dog to catch the cat, she swallowed the cat to catch the bird, she swallowed the bird to catch the spider that wriggled and wriggled and tickled inside her. She swallowed the spider to catch the fly, but I don't know why she swallowed the fly. I guess she'll die.There was an old lady who swallowed a horse. (Beat) She's dead, of course!
- The Dethklok song "Bloodrocuted" tells of an electrician being chased through the woods by bounty hunters because he just so happens to look exactly like a wanted criminal with a large bounty on his head. He stumbles upon an electrical substation and manages to kill the bounty hunters by cutting his arms and electrifying a puddle of his own blood for them to step in. He then realizes that he has no way to patch himself up and will therefore bleed to death very soon.
- Smash Mouth's Everyday Superhero:
I try to hide my true identity
But no-one knows it's only me.
- In The Epic of Gilgamesh, the gods created humanity so that they would work and feed the gods, allowing them to live in leisure. Then the gods couldn't stand the noise people made, so they tried to exterminate them a few times, culminating with The Great Flood. It was apparently successful...until they realized that there was no one left to feed them, nor anything to eat...
- In the Greek myth King Midas and the golden touch, a greedy king named Midas makes a wish from Dionysus that everything he touches would turn to gold. He gets the wish, and is overjoyed... Until he realizes too late that this means he can no longer eat or drink anything...or touch his daughter. If he had thought more carefully (or just listened to Dionysus' warning that it was a stupid wish), he might have instead just wished for the ability to turn stuff into gold (but not every single thing he touched). Fortunately for Midas, Dionysus took pity on him and showed him how to remove his golden touch and turn his daughter and everything else back to normal.
- At least in the original. Many people are told the story as a classic Jerkass Genie story.
- The matches regarding the Pure Wrestling Title belt in Ring of Honor were often anything but, as the rules were loose enough for wrestlers to do many, many unintended things. It did achieve the goal of having matches unlike any other promotion was having at the time though, so they just went with it.
- CM Punk's dormant "feud" with Delirious started back up in IWA Mid-South with Punk in pursuit of Delirious's Light Heavyweight Title, but when Punk challenged and beat Delirious, he didn't win the belt because he was above the weight limit.
- Chris Hero mocked Bryan Danielson for this in 2005 when he answered Hero's challenge for an ROH World Title match by signing a contract and then sending it to Hero at CZW so he could sign it too. See, Hero could have just as well have had anybody sign the contract.
- At the 2009 Slammiversary, Jeff Jarrett said he had no desire to win any TNA titles, he only cared about making sure Mick Foley dropped his. Yet Jarrett repeatedly sabotaged AJ Styles' efforts to defeat Mick Foley, even though AJ winning would have meant Mick would have lost his title.
- At nCw Femme Fatales, Mary Lee Rose had been very open with the fact she had no desire to wrestle Cheerleader Melissa, which is understandable. However, she still spent a lot of time harassing Melissa, interfering in her matches and such. Mary Lee Rose did want to wrestle someone eventually, so she issued an open challenge. Not only was Cheerleader Melissa the first person to accept, but she couldn't help but point out how dumb Rose was for not realizing that would happen. Unfortunately for Melissa, Mary Lee Rose's manager, Mademoiselle Rachelle, lobbied to stop the match from happening and pitted Melissa against Yumi Ohka instead.
- Frankie Kazarian and Christopher Daniels are accusing AJ Styles of getting a binge drinking crackhead pregnant. Well, the show is called TNA, but what is AJ's response to this? Challenge Christopher Daniels to a match on the stipulation he will admit to being the father if Daniels can beat him, but will take a paternity test to find out for sure if he beats Daniels.
- In WWE, Seth Rollins made the exact same "open challenge even though I've been antagonizing someone I have no desire to wrestle" mistake. In this case, it was Dean Ambrose who answered.
- Bleak Expectations: This trope describes many of Harry Biscuit's ideas, and Pip Bin's. The fact the two live long enough to reach adulthood is astounding. At one point, the latter falls foul of Admiral Hardthrasher, when Pip lets loose he's responsible for the death of the admiral's brothers - specifically the ones he liked. In order to defend himself, Pip sets Hardthrasher on fire and sinks his ships... despite not knowing how to swim. And the ships are out at sea. This prompts Pip, in a very rare moment of self-awareness to admit he hadn't thought this through.
- One Paranoia mission introduces the new Mandatory Bonus Duty of Executive Officer, who (in addition to being the Team Leader's Number Two) gets a brevet promotion for the purpose of wearing a higher-clearance uniform — the idea is that Commies will mistake him for the Team Leader and concentrate their fire on him instead. As usual for Paranoia, The Computer failed to consider what might happen when others made the same mistake:
Green-clearance Team Leader: All right, men, let's go!
Random bystander: Hey, why are you letting him boss you around?
"Blue"-clearance Executive Officer: Hey, yeah! [shoots the Team Leader] All right, men, let's go!
- In one Time of Judgment scenario in Werewolf: The Apocalypse, the Silent Striders decide to join the Wyrm's forces and goad the Wyrm's servants into attacking Grandmother, in the hopes of weakening both the Wyrm and Grandmother. They do so by passing through the Black Spiral Labyrinth, which hopelessly corrupts them. Instead of fighting Grandmother, the corrupted Silent Striders attack the Garou Nation.
- Betrayal at House on the Hill: One scenario involves the traitor attempting to send the house and everyone in it, including themself, to hell. If they win, in the end text they realise too late that this probably wasn't such a good idea.
- Another scenario has the traitor making voodoo dolls of the other players. If they win, they destroy the dolls - and then realize that destroying a voodoo doll of yourself is quite possibly a terrible, terrible idea.
- The title character of Hamilton has been accused of embezzling money from the U.S. government. In fact, what he's doing is totally legal, just not exactly ethical: he has been having an affair and the payments are to the woman's husband, who's been blackmailing him for some time. In order to refute the accusation, confesses to the affair and the payments. True, his political rivals stop accusing him of embezzlement, but to the voting public of 1800s America, adultery isn't much better. In a Cut Song, his wife's sister tears him a new one for this:
- Congratulations. You have invented a new kind of stupid / A damage you can never undo kind of stupid / An "open all the cages at the zoo" kind of stupid / Clearly, you didn't think this trough / Kinda stupid!
- In Pokémon Live!, one trainer that challenges MechaMew2 has his Electrode use Selfdestruct in the hopes that the move would be returned... overlooking the fact that using the move made his Electrode faint.
- In Episode 8, Weiss falls out of the sky. Jaune leaps up and catches her in his arms. He manages to look badass for a moment, then realizes that they are now both in midair with no landing strategy. He crashes, but at least provides Weiss' landing cushion.
- This is the reason why we catch Team RNJR (Ruby and the remains of Team JNPR) walking through the forest in the first episode of Volume 4: Ruby decided they should walk to Mistral at the end of Volume 3. On the other side of the continent she lives on.
- In Volume 5, Raven planned to steal the Relic of Knowledge to keep Salem away from her tribe. Yang, however, makes her aware that if Salem was willing to pursue her when she thought Raven was only harboring the Spring Maiden, then she would definitely be on her hitlist upon learning that Raven not only is the Spring Maiden, but is also carrying one of the Relics she's after. Raven's shocked to discover that she didn't exactly consider the implications.
- In one skit in RWBY Chibi, Cinder demonstrates a Dynamite Candle for her "evil class" (consisting of Roman, Neo, Emerald, and Mercury). When Emerald points out that the trap is too obvious, Cinder misinterprets it as her henchwoman not understanding the concept and lights the dynamite right then and there to demonstrate. She has just enough time to realize what a bad move that was before the dynamite explodes.
- DSBT InsaniT:
- Dr. Havoc's Diary: In Episode 17, Brock sneaks onto Havoc's submarine by cutting a hole in the side with a welding gun. Guess what eventually happens?
- Nomad of Nowhere: In the first episode, Toph and her team (sans Skout) decide to set the forest on fire to flush out and capture the titular Nomad for good... while they're still in it.