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Idioms are fun phrases that mean something different than the actual words inside them. People use them every day to make speaking and writing much more colorful and exciting. In this article, you will learn fifty special expressions connected to impossible situations and hopeless tasks.
In this lesson, we’ll look at idioms that mean trying to do something that cannot be done. Let’s get started and explore some of these helpful expressions.
Idioms for Impossible Situations
1. Barking up the wrong tree
Definition: To pursue a completely mistaken course of action or accuse the wrong person.
Used in a Sentence: If you think I took your colored pencils, you are barking up the wrong tree. / The detective was barking up the wrong tree because the real clue was elsewhere.
Similar Expressions: Making a false assumption / Looking in the wrong place
2. Needle in a haystack
Definition: Something that is almost impossible to find because it is hidden in a huge space.
Used in a Sentence: Finding my tiny contact lens on the grass felt like looking for a needle in a haystack. / Searching for a specific toy in that messy attic is like finding a needle in a haystack.
Similar Expressions: Nearly impossible to locate / Extremely hard to find
3. Chase rainbows
Definition: To pursue an unrealistic goal or try to achieve something that cannot happen.
Used in a Sentence: Stop wasting time trying to fly by yourself and quit chasing rainbows. / Dreaming of winning the lottery without buying a ticket is just chasing rainbows.
Similar Expressions: Pursue impossible dreams / Seek the unattainable
4. Catch the wind
Definition: To try to capture or control something that is completely untouchable.
Used in a Sentence: Trying to stop rumors from spreading is like trying to catch the wind. / You cannot hold onto water or catch the wind with your bare hands.
Similar Expressions: Attempt the impossible / Grab the untouchable
5. Milk a bull
Definition: To attempt a task that has zero chance of producing any results.
Used in a Sentence: Asking him to change his mind is like trying to milk a bull. / That project has no data and will not work since you cannot milk a bull.
Similar Expressions: Waste your effort / Do the impossible
6. Square peg in a round hole
Definition: A person who does not fit into a specific group, job, or situation.
Used in a Sentence: Liam felt like a square peg in a round hole when he joined the advanced physics club. / Trying to make that oversized table fit in the tiny nook made it a square peg in a round hole.
Similar Expressions: Misfit in society / Complete mismatch
7. Pull yourself up by your bootstraps
Definition: To try to improve a terrible situation using only your own difficult efforts.
Used in a Sentence: When the business failed, the owner had to pull himself up by his bootstraps. / It is tough to pull yourself up by your bootstraps when everything goes wrong.
Similar Expressions: Overcome adversity / Save yourself
8. Bring ice to the North Pole
Definition: To do something completely useless because it is already abundantly present.
Used in a Sentence: Selling warm winter coats in the middle of a desert is like bringing ice to the North Pole. / Bringing extra pencils to the classroom is like bringing ice to the North Pole.
Similar Expressions: Do redundant work / Carry coals to Newcastle
9. Count your chickens before they hatch
Definition: To assume success before an event has actually happened or become certain.
Used in a Sentence: Do not celebrate winning the game yet or count your chickens before they hatch. / She bought party decorations before passing the test, which was counting chickens before they hatch.
Similar Expressions: Assume victory early / Be overconfident
10. Reach for the moon
Definition: To attempt an extraordinarily difficult goal that is likely out of reach.
Used in a Sentence: Even though it is hard, you should always reach for the moon in your career. / Building a working spaceship at age ten is like reaching for the moon.
Similar Expressions: Aim extremely high / Seek grand goals
11. Catch lightning in a bottle
Definition: To try to capture a rare stroke of luck or magic that cannot be repeated.
Used in a Sentence: Winning the championship two years in a row is like trying to catch lightning in a bottle. / The musician tried to recreate his first hit song, but it was like catching lightning in a bottle.
Similar Expressions: Reproduce the impossible / Capture magic
12. Build castles in the air
Definition: To daydream about impossible plans that have no foundation in reality.
Used in a Sentence: Instead of doing homework, he sat by the window building castles in the air. / We need realistic plans, not just building castles in the air.
Similar Expressions: Daydream idly / Form unrealistic plans
13. Turn water into wine
Definition: To perform an absolute miracle when faced with a hopeless problem.
Used in a Sentence: Fixing this broken computer with no spare parts is like trying to turn water into wine. / The coach had to turn water into wine to win with our beginner team.
Similar Expressions: Perform miracles / Work wonders
14. Split hairs
Definition: To argue about tiny, unimportant details that do not change the impossible situation.
Used in a Sentence: There is no point in splitting hairs over a two-minute delay when the train is canceled. / The teacher told us to stop splitting hairs and focus on the main topic.
Similar Expressions: Argue minor points / Overanalyze details
15. Hold back the tide
Definition: To try to stop an unstoppable force or inevitable change.
Used in a Sentence: Trying to stop time from moving forward is like holding back the tide. / Complaining about technology is like trying to hold back the tide.
Similar Expressions: Fight the inevitable / Resist unstoppable forces
16. Whistle in the wind
Definition: To make an appeal or effort that no one hears or cares about.
Used in a Sentence: Complaining about the cafeteria food to the chef is just whistling in the wind. / Asking the loud dog to quiet down with a whisper is like whistling in the wind.
Similar Expressions: Shout into a void / Make useless pleas
17. Teach a fish to climb trees
Definition: To try to train someone to do something completely outside their natural abilities.
Used in a Sentence: Asking me to solve advanced calculus is like trying to teach a fish to climb trees. / Expecting the clumsy puppy to do ballet is like teaching a fish to climb trees.
Similar Expressions: Force the unnatural / Attempt absurd training
18. Measure the ocean with a teaspoon
Definition: To undertake a massive task using tools that are far too small.
Used in a Sentence: Trying to bail out the flooded basement with a cup is like measuring the ocean with a teaspoon. / Memorizing the entire dictionary in a day is like measuring the ocean with a teaspoon.
Similar Expressions: Use inadequate tools / Undertake the infinite
19. Squeeze blood from a turnip
Definition: To try to get money or help from someone who has absolutely nothing to give.
Used in a Sentence: Asking my little brother to lend me fifty dollars is like trying to squeeze blood from a turnip. / The company had no extra funds, so getting a refund was like squeezing blood from a turnip.
Similar Expressions: Extract the impossible / Demand the unavailable
20. Hit a brick wall
Definition: To reach a complete stop in progress because of an insurmountable obstacle.
Used in a Sentence: We were solving the puzzle smoothly until we hit a brick wall on level five. / Writing the essay was going well until I hit a brick wall of writer’s block.
Similar Expressions: Reach a dead end / Stop progressing
21. Beat a dead horse
Definition: To waste energy continuing an argument or effort that is already finished.
Used in a Sentence: There is no use discussing the broken vase anymore because we are just beating a dead horse. / Arguing about who lost the game yesterday is beating a dead horse.
Similar Expressions: Waste effort / Revive lost causes
22. Pluck stars from the sky
Definition: To attempt a task that is beyond human capability.
Used in a Sentence: Expecting me to finish this giant project in five minutes is asking me to pluck stars from the sky. / Wishing for a magic wand to fix everything is like trying to pluck stars from the sky.
Similar Expressions: Ask the impossible / Seek unreachable heights
23. Ride two horses at once
Definition: To try to do two mutually exclusive or impossible things at the same time.
Used in a Sentence: Trying to play two different video games simultaneously is like riding two horses at once. / You cannot keep your job and travel for a year because you cannot ride two horses at once.
Similar Expressions: Split focus impossibly / Do contradictory tasks
24. Look for a needle in a bottle of hay
Definition: An alternative way of describing a search that has zero chance of success.
Used in a Sentence: Dropping my ring in the deep forest means I am looking for a needle in a bottle of hay. / Finding that one specific paper in the storage locker is like looking for a needle in a bottle of hay.
Similar Expressions: Impossible search / Hidden quest
25. Move mountains
Definition: To achieve an amazingly difficult feat against all odds.
Used in a Sentence: The dedicated volunteers worked together to move mountains and finish the park. / It will take a miracle or an effort to move mountains to pass this test.
Similar Expressions: Overcome massive obstacles / Achieve the impossible
26. Swim upstream
Definition: To struggle against strong opposition, rules, or difficult conditions.
Used in a Sentence: Trying to convince the whole committee to change the rules feels like swimming upstream. / Being the only beginner in an advanced class is like swimming upstream.
Similar Expressions: Fight the current / Struggle against odds
27. Walk on water
Definition: To be expected to perform flawless miracles in an impossible situation.
Used in a Sentence: The boss expects me to fix every single software bug instantly as if I can walk on water. / Nobody can walk on water when faced with a broken engine and no tools.
Similar Expressions: Perform miracles / Be superhuman
28. Fit a square peg into a round hole
Definition: To force something into a position where it completely does not belong.
Used in a Sentence: Trying to make that computer program run on an ancient phone is like fitting a square peg into a round hole. / He felt like he was fitting a square peg into a round hole at his new job.
Similar Expressions: Force a mismatch / Wrong placement
29. Catch smoke with your hands
Definition: To try to grasp something completely intangible or unreal.
Used in a Sentence: Trying to pin down his vague explanation is like trying to catch smoke with your hands. / Secrets fly away just like trying to catch smoke with your hands.
Similar Expressions: Grab the intangible / Hold nothing
30. Build a bridge to nowhere
Definition: To invest time and money into a project that serves no purpose or fails.
Used in a Sentence: Planning a party that no one can attend is like building a bridge to nowhere. / Fixing a machine that is completely beyond repair is building a bridge to nowhere.
Similar Expressions: Useless project / Pointless effort
31. Cry for the moon
Definition: To ask for something that is completely unattainable or impossible to get.
Used in a Sentence: Asking for a pet dragon for your birthday is crying for the moon. / Wishing to be a superhero in real life is like crying for the moon.
Similar Expressions: Desire the impossible / Ask too much
32. Push a boulder uphill
Definition: To engage in a continuous, exhausting struggle with no permanent progress.
Used in a Sentence: Studying for a test in a subject you hate feels like pushing a boulder uphill. / Keeping the playroom clean with toddlers is like pushing a boulder uphill.
Similar Expressions: Endless struggle / Uphill battle
33. Paint the wind
Definition: To attempt to represent or capture something that cannot be seen or touched.
Used in a Sentence: Trying to describe how excitement feels to a robot is like trying to paint the wind. / Writing a rule for something invisible is like attempting to paint the wind.
Similar Expressions: Capture the invisible / Do the unrealizable
34. Turn lead into gold
Definition: To attempt to transform something worthless into something extremely valuable.
Used in a Sentence: Fixing this rusty old bicycle to look brand new is like trying to turn lead into gold. / The struggling bakery tried to turn lead into gold with a new cookie recipe.
Similar Expressions: Alchemy attempt / Transform the worthless
35. Make a silk purse out of a sow’s ear
Definition: To try to make something fine and beautiful out of inferior materials.
Used in a Sentence: Trying to sew this torn, cheap fabric into a stylish dress is making a silk purse out of a sow’s ear. / Restoring that completely wrecked car is like making a silk purse out of a sow’s ear.
Similar Expressions: Upgrade the impossible / Beautify scrap
36. Run before you can walk
Definition: To attempt complex tasks before mastering the basic foundations.
Used in a Sentence: Trying to solve advanced calculus before learning addition is running before you can walk. / Do not start building the robot chassis before you can walk by learning basic wiring.
Similar Expressions: Skip steps / Rush progress
37. Grab at straws
Definition: To look for any tiny shred of hope in a completely desperate situation.
Used in a Sentence: When the computer crashed, we were grabbing at straws to save our report. / With only one second left in the game, the losing team was grabbing at straws.
Similar Expressions: Desperate hope / Final attempt
38. Split an atom with a feather
Definition: To attempt an immensely delicate and impossible scientific feat.
Used in a Sentence: Trying to fix the broken watch gear with a twig is like trying to split an atom with a feather. / Calming the angry crowd with one whisper felt like trying to split an atom with a feather.
Similar Expressions: Delicate impossibility / Extreme challenge
39. Empty the ocean with a bucket
Definition: To try to complete an infinitely large job using a tiny container.
Used in a Sentence: Cleaning up the stadium mess with a hand broom is like trying to empty the ocean with a bucket. / Trying to erase every digital copy of a rumor is like emptying the ocean with a bucket.
Similar Expressions: Endless task / Infinite labor
40. Put the cart before the horse
Definition: To do things in the wrong order, making the task unnecessarily difficult.
Used in a Sentence: Buying paint before you even build the doghouse is putting the cart before the horse. / Trying to take the final exam before studying is putting the cart before the horse.
Similar Expressions: Reverse order / Do things backward
41. Fire arrows at the sun
Definition: To attempt an attack or goal that is so far out of reach it has no effect.
Used in a Sentence: Complaining about the weather laws to city hall is like firing arrows at the sun. / Trying to defeat the giant corporation with one letter is like firing arrows at the sun.
Similar Expressions: Futile attack / Useless effort
42. Look for footprints in the water
Definition: To search for evidence of something that leaves no trace behind.
Used in a Sentence: Trying to trace where the digital glitch came from is like looking for footprints in the water. / Investigating the mysterious disappearance with no clues is like looking for footprints in the water.
Similar Expressions: Trace the untraceable / Search for ghosts
43. Catch a falling star
Definition: To attempt to capture something fleeting, beautiful, and physically impossible to hold.
Used in a Sentence: Trying to freeze a fleeting moment of pure magic is like trying to catch a falling star. / Expecting perfection on your very first try is like trying to catch a falling star.
Similar Expressions: Grab the impossible / Capture beauty
44. Navigate without a compass
Definition: To try to solve a complex problem with zero guidance or directions.
Used in a Sentence: Entering the dark maze without a map meant we had to navigate without a compass. / Starting a brand new business with no plan is like trying to navigate without a compass.
Similar Expressions: Go blindly / Proceed without guidance
45. Nail jelly to a wall
Definition: To try to organize or control something that is completely unstable and slippery.
Used in a Sentence: Trying to get the energetic toddlers to sit still for a photo is like trying to nail jelly to a wall. / Explaining the complex rules to the class felt like nailing jelly to a wall.
Similar Expressions: Control the uncontrollable / Stabilize the chaotic
46. Build on sand
Definition: To create a plan or project on a weak foundation that will collapse.
Used in a Sentence: Starting a big group project with no rules or leader is building on sand. / Making promises you cannot keep is like building a house on sand.
Similar Expressions: Weak foundation / Unstable plan
47. Weave ropes of sand
Definition: To attempt a task that lacks any structural possibility of holding together.
Used in a Sentence: Trying to unite the arguing team members with no compromise was like weaving ropes of sand. / Writing a contract with no solid agreements is weaving ropes of sand.
Similar Expressions: Impossible construction / Fragile effort
48. Sitch in time
Definition: An attempt to fix a broken situation when it is already too late to save it.
Used in a Sentence: Trying to fix the engine after it exploded is like trying to save a lost cause. / Arguing after the deadline has passed is a useless effort.
Similar Expressions: Late rescue / Vain attempt
49. Try to warm a glacier with a match
Definition: To use an insignificant amount of effort against an overwhelmingly massive problem.
Used in a Sentence: Trying to solve global warming with one planted flower is like trying to warm a glacier with a match. / Paying off a huge debt with a single penny is like trying to warm a glacier with a match.
Similar Expressions: Inadequate solution / Useless warmth
50. Catch a shadow
Definition: To attempt to physically grab or control something that has no substance.
Used in a Sentence: Trying to prove the rumor was true without any facts was like trying to catch a shadow. / Chasing fame without talent is like trying to catch a shadow.
Similar Expressions: Chase the unreal / Grasp nothing
Exercise to Practice
- If you think I took your colored pencils, you are barking up the wrong tree because I was outside.
- Finding my tiny contact lens on the thick green grass felt like looking for a needle in a haystack.
- Stop wasting time trying to fly by yourself with paper wings and quit chasing rainbows.
- You cannot hold onto water or catch the wind with your bare hands when swimming in the pool.
- Asking him to change his mind about pizza is like trying to milk a bull.
- Liam felt like a square peg in a round hole when he joined the advanced physics club and loved every minute.
- When the business failed, the owner had to pull himself up by his bootstraps to open a new shop.
- Selling warm winter coats in the middle of a hot summer desert is like bringing ice to the North Pole.
- Do not celebrate winning the science fair yet or count your chickens before they hatch.
- Even though it is hard, you should always reach for the moon in your art class projects.
- Winning the school spelling bee two years in a row is like trying to catch lightning in a bottle.
- Instead of doing homework, he sat by the window building castles in the air and finished his math early.
- Fixing this broken computer with no spare parts is like trying to turn water into wine.
- There is no point in splitting hairs over a two-minute delay when the train arrives on time.
- Trying to stop time from moving forward is like holding back the tide with your hands.
Answer Key
- True
- True
- True
- True
- True
- False
- True
- True
- True
- True
- True
- False
- True
- False
- True
Conclusion
Learning these idioms helps you understand English much better and gives you fun new ways to talk about difficult tasks and impossible situations. You can use them when talking about school projects, sports challenges, or everyday puzzles with your friends and family.
Try using one or two of these expressions in a conversation or a story this week. Not only will your writing sound more exciting, but you will also have fun practicing your new skills.
Frequently Asked Questions
What are some common idioms for impossible situations?
Some common idioms include needle in a haystack, barking up the wrong tree, and chasing rainbows. These expressions are often used in everyday conversation to talk about tasks that are very hard or impossible to complete.
Why do we use idioms in English?
Idioms make our language much more colorful, expressive, and fun than using plain words. They help us share big ideas and feelings in creative ways that people easily recognize.
How can I learn these idioms faster?
You can learn idioms faster by using them in daily sentences, writing short stories, and practicing with a friend. Making flashcards with pictures can also help you remember what each phrase means.
Are idioms used in everyday conversation?
Yes, native English speakers use idioms all the time during casual chats, television shows, and books. Learning them helps you understand jokes, stories, and conversations much more naturally.
Can idioms have more than one meaning?
Most idioms have one main accepted meaning, but how people use them can vary slightly depending on the context. Reading example sentences helps you see the exact way each phrase works.
