Idioms are wonderful figurative expressions where the combined words create a special meaning entirely different from their literal definitions. People use them to make their speaking and writing more colorful, lively, and expressive. In this article, you will learn fifty unique idioms related to regret, looking back with hindsight, and wishing you could change the past.
In this lesson, we’ll look at idioms that mean feeling sorry about past choices or wishing things had happened differently. Let’s get started and explore some of these helpful expressions.
Idioms for Regret
1. Cry over spilled milk
Definition: To waste time and energy worrying or feeling sad about a mistake that cannot be undone.
Used in a Sentence: Dropping your lunch tray is annoying, but there is no use crying over spilled milk. / He failed the quiz because he did not study, and now he is just crying over spilled milk instead of preparing for the next one.
Similar Expressions: Waste time regretting / Worry uselessly
2. Eat your words
Definition: To admit publicly that you were completely wrong about something you said earlier.
Used in a Sentence: After the small soccer team won the championship, he had to eat his words about them being terrible. / She told everyone the puzzle was impossible, but when she finished it in a minute, she had to eat her words.
Similar Expressions: Admit a mistake / Take back statements
3. Kick yourself
Definition: To feel angry and annoyed with yourself for making a silly mistake or missing a good opportunity.
Used in a Sentence: He wanted to kick himself when he realized he left his favorite jacket at the park. / She could have won the prize if she entered the contest, and now she is just kicking herself for waiting too long.
Similar Expressions: Regret bitterly / Be angry at yourself
4. Rue the day
Definition: To deeply regret something you did or a choice you made in the past.
Used in a Sentence: He knew he would rue the day he decided to skip studying for his history exam. / She realized she would rue the day she borrowed her sister’s markers without asking.
Similar Expressions: Deeply regret / Wish you never did it
5. Eat humble pie
Definition: To admit that you were wrong and accept humiliation or regret after being overconfident.
Used in a Sentence: After bragging about how easy the video game level was before failing immediately, he had to eat humble pie. / She ate humble pie when her art project scored lower than the project she had laughed at.
Similar Expressions: Apologize humbly / Face humiliation
6. Have second thoughts
Definition: To start feeling doubt or regret about a decision you previously made.
Used in a Sentence: Right before boarding the roller coaster, he started having second thoughts about whether he wanted to ride. / She bought the bright pink shoes, but now she is having second thoughts and wishes she picked blue.
Similar Expressions: Doubt a choice / Reconsider
7. Bite your tongue
Definition: To stop yourself from saying something you might instantly regret later.
Used in a Sentence: When his friend made a silly comment, he had to bite his tongue to keep from arguing. / She wanted to complain about the chores, but she bit her tongue and helped out anyway.
Similar Expressions: Keep quiet / Restrain speech
8. Wish the ground would swallow you up
Definition: To feel so deeply embarrassed and regretful that you want to hide from everyone.
Used in a Sentence: When he tripped on the stage during the school play, he wished the ground would swallow him up. / Making a mistake while reading aloud made her wish the ground would swallow her up.
Similar Expressions: Feel mortified / Want to hide
9. A bitter pill to swallow
Definition: An unpleasant truth, failure, or regretful reality that you are forced to accept.
Used in a Sentence: Finding out he did not make the soccer team was a bitter pill to swallow. / Losing the class election after working so hard felt like a bitter pill to swallow.
Similar Expressions: Hard truth / Painful reality
10. Turn back the clock
Definition: To wish you could return to the past in order to change a regretful decision.
Used in a Sentence: If he could turn back the clock, he would have started studying for his math test a week earlier. / She wished she could turn back the clock and take back the harsh words she said.
Similar Expressions: Undo the past / Reverse time
11. Hindsight is twenty-twenty
Definition: It is very easy to understand what you should have done only after looking back on a situation.
Used in a Sentence: He realized he should have worn a heavier jacket, but hindsight is twenty-twenty. / She wished she had saved her allowance sooner, realizing hindsight is twenty-twenty.
Similar Expressions: Clear in retrospect / Easy to see later
12. Repent at leisure
Definition: To experience a long period of regret after rushing into a bad decision without thinking.
Used in a Sentence: He married his toy collection choices too quickly and spent the afternoon repenting at leisure. / Rushing through your homework means you will have to repent at leisure when you get bad grades.
Similar Expressions: Regret at length / Pay for haste
13. Lock the barn door after the horse is stolen
Definition: To try and fix a problem or take precautions only after the damage is already done.
Used in a Sentence: Buying a bike lock after his bicycle was stolen was like locking the barn door after the horse is stolen. / Studying hard the day after the test failed is like locking the barn door after the horse is stolen.
Similar Expressions: Too late for action / Prevent too late
14. Live to regret it
Definition: To make a choice now that will cause you deep sorrow and regret in the future.
Used in a Sentence: If you skip practicing your piano scales, you will live to regret it during the recital. / He ignored his mother’s warning and lived to regret it when his toy broke.
Similar Expressions: Pay later / Face future sorrow
15. A missed opportunity
Definition: A chance or moment of success that you failed to take advantage of and now regret.
Used in a Sentence: Not signing up for the school spelling bee turned out to be a major missed opportunity for him. / She viewed missing the afternoon museum trip as a big missed opportunity.
Similar Expressions: Lost chance / Passed up opening
16. Kick yourself around the block
Definition: A playful way to describe feeling extremely annoyed with yourself over a mistake.
Used in a Sentence: Leaving his science notebook at home made him want to kick himself around the block. / She could have answered the bonus question easily, leaving her wanting to kick herself around the block.
Similar Expressions: Regret deeply / Be furious at yourself
17. Wring your hands
Definition: To twist your fingers together anxiously out of worry, regret, or nervousness.
Used in a Sentence: While waiting for the test grades, she sat at her desk wringing her hands in regret over skipped questions. / He spent the afternoon wringing his hands over whether he should apologize.
Similar Expressions: Fret anxiously / Worry deeply
18. Wear sackcloth and ashes
Definition: A traditional expression for expressing deep sorrow, mourning, and extreme regret.
Used in a Sentence: After losing the championship game due to a silly foul, he felt like walking around in sackcloth and ashes. / She did not need to wear sackcloth and ashes just because she dropped a single glass plate.
Similar Expressions: Mourn deeply / Show extreme remorse
19. A pang of regret
Definition: A sudden, sharp feeling of sorrow or guilt about a past action.
Used in a Sentence: He felt a sudden pang of regret when he saw how sad his friend looked after the argument. / Leaving her old school behind gave her a sharp pang of regret.
Similar Expressions: Wave of remorse / Sudden sorrow
20. Curse your luck
Definition: To feel angry and regretful about unfortunate circumstances or bad timing.
Used in a Sentence: When it started pouring rain right as their outdoor picnic began, everyone began to curse their luck. / He cursed his luck when his computer crashed right before saving his essay.
Similar Expressions: Blame fortune / Feel unlucky
21. Regret passing up
Definition: To feel sorry for declining an invitation or a wonderful chance.
Used in a Sentence: He began to regret passing up the chance to join the basketball team trip. / She regretted passing up the extra slice of chocolate birthday cake.
Similar Expressions: Sorry for declining / Missed choice
22. Carry a heavy heart
Definition: To feel weighed down by sadness, guilt, or regret over past events.
Used in a Sentence: Walking home after the disagreement with his best friend left him carrying a heavy heart. / She carried a heavy heart all evening after forgetting her grandmother’s birthday.
Similar Expressions: Feel burdened / Feel sorrowful
23. Wish you had never been born
Definition: An exaggerated way of expressing extreme embarrassment and regret over a terrible blunder.
Used in a Sentence: Tripping over the rug in front of the whole assembly made him feel like he wished he had never been born. / Making that awkward speech error made her feel like she wished she had never been born.
Similar Expressions: Feel mortified / Extreme embarrassment
24. Kick a dead horse
Definition: To keep worrying or arguing about a past regret that cannot be changed.
Used in a Sentence: Complaining about last week’s lost match is just kicking a dead horse; focus on the next game. / There is no use kicking a dead horse over the broken vase.
Similar Expressions: Waste effort / Rehash the past
25. A ghost of the past
Definition: An old regret or memory that comes back to haunt you.
Used in a Sentence: Seeing his old kindergarten classroom brought back a ghost of the past regarding a lost toy. / Mistakes from last year felt like a ghost of the past when he took similar tests.
Similar Expressions: Past memory / Old regret
26. Sigh with regret
Definition: To let out a long breath of sorrow when thinking about a past mistake.
Used in a Sentence: Looking at his low quiz score, he could only sigh with regret. / She looked at the broken figurine and let out a quiet sigh with regret.
Similar Expressions: Breathe sorrow / Lament softly
27. Haunted by memories
Definition: Having past regrets and embarrassing moments constantly replay in your mind.
Used in a Sentence: For days after the speech stumble, he felt haunted by memories of the audience laughing. / She was haunted by memories of leaving her art project behind.
Similar Expressions: Troubled by the past / Plagued by thoughts
28. Swallow your pride
Definition: To push aside your ego in order to apologize for a past mistake or regret.
Used in a Sentence: He had to swallow his pride and say sorry to his brother after starting the argument. / Swallowing her pride allowed her to admit she was wrong about the directions.
Similar Expressions: Drop your ego / Admit fault
29. A remorseful heart
Definition: Feeling genuine sorrow, regret, and pity for having done something wrong.
Used in a Sentence: With a remorseful heart, he apologized to the teacher for interrupting the lesson. / She approached her friend with a remorseful heart after the misunderstanding.
Similar Expressions: Sorry soul / Regretful spirit
30. Look back in sorrow
Definition: To review past events with feelings of sadness and regret.
Used in a Sentence: When he thought about his missed piano practice, he could only look back in sorrow. / She looked back in sorrow at the friendships that faded away.
Similar Expressions: Reflect sadly / Review with regret
31. Rue the hour
Definition: To feel deep regret for a specific moment or time spent doing something wrong.
Used in a Sentence: He knew he would rue the hour he agreed to clean the entire attic by himself. / She began to rue the hour she signed up for the extra cleaning chores.
Similar Expressions: Regret the moment / Wish away time
32. Kick yourself from here to Sunday
Definition: An exaggerated expression for feeling extremely angry at yourself over a major error.
Used in a Sentence: Losing his house keys made him want to kick himself from here to Sunday. / She could have won the grand prize if she checked her spelling, leaving her wanting to kick herself from here to Sunday.
Similar Expressions: Regret immensely / Be furious at self
33. A conscience prick
Definition: A sudden sting of guilt and regret inside your mind for doing something improper.
Used in a Sentence: Taking the extra cookie without asking gave him a sharp conscience prick. / She felt a conscience prick when she realized she forgot to invite her neighbor.
Similar Expressions: Sting of guilt / Guilty feeling
34. Beat your breast
Definition: To express grief, sorrow, and regret dramatically over a bad outcome.
Used in a Sentence: There is no need to beat your breast over a dropped pencil. / He started to beat his breast in dramatic regret when his favorite team lost.
Similar Expressions: Mourn loudly / Lament dramatically
35. Cry into your beer
Definition: To sit around feeling sorry for yourself and regretting past misfortunes.
Used in a Sentence: Instead of crying into your beer over losing the match, let us practice harder. / Stop crying into your beer and go fix the broken toy.
Similar Expressions: Pity yourself / Mourn losses
36. A day late and a dollar short
Definition: Arriving too late or missing out because your preparation or action came after the regretful moment.
Used in a Sentence: Trying to study after the exam already ended was a day late and a dollar short. / Signing up for the club trip after the bus left was a day late and a dollar short.
Similar Expressions: Too late / Missed the boat
37. Wish you had kept your mouth shut
Definition: Regretting something impulsive or rude that you just said out loud.
Used in a Sentence: As soon as he made the sarcastic comment, he wished he had kept his mouth shut. / She realized her joke hurt her friend’s feelings and instantly wished she had kept her mouth shut.
Similar Expressions: Regret speaking / Wish for silence
38. Weep over the past
Definition: To spend excessive time feeling sad about old mistakes and regrets.
Used in a Sentence: You cannot change history by sitting around and weeping over the past. / Moving forward is better than weeping over the past.
Similar Expressions: Cry over old times / Mourn history
39. A thorn in your side
Definition: A lingering past mistake or regret that continues to annoy and bother you.
Used in a Sentence: Getting a bad grade on his transcript remained a thorn in his side all semester. / That forgotten homework assignment was a constant thorn in her side.
Similar Expressions: Persistent annoyance / Lingering regret
40. Eat crow
Definition: To accept a humiliating defeat or regretful realization after being proven wrong.
Used in a Sentence: After saying no one could beat his high score, he had to eat crow when his sister beat it. / He ate crow when his teacher corrected his incorrect science theory.
Similar Expressions: Admit defeat / Humble yourself
41. A sigh of remorse
Definition: A quiet sound expressing sorrow for a past action.
Used in a Sentence: He let out a deep sigh of remorse when returning the borrowed book late. / She offered a quiet sigh of remorse after breaking her promise.
Similar Expressions: Sound of regret / Remorseful breath
42. Wish you had taken the road not taken
Definition: Regretting the choice you made and wondering how life would be if you chose differently.
Used in a Sentence: Wondering about his alternative career path made him think of the road not taken. / She often looked back at her choices and wondered about the road not taken.
Similar Expressions: Wonder about alternatives / Regret a path
43. Cry over broken toys
Definition: To feel regret and sadness over material things or situations that cannot be fixed.
Used in a Sentence: Breaking his model airplane made him sit and cry over broken toys for an hour. / Do not waste time crying over broken toys; let us build a new one.
Similar Expressions: Mourn loss / Regret breakage
44. A bitter pill
Definition: A harsh reality or regretful consequence that is difficult to accept.
Used in a Sentence: Realizing he caused the team to lose was a bitter pill. / Accepting that her painting did not win was a bitter pill to swallow.
Similar Expressions: Hard reality / Unpleasant truth
45. Regret at leisure
Definition: Making a hasty choice and suffering the long-term regret that follows.
Used in a Sentence: Choosing your classes without reading the descriptions means you will regret at leisure. / Hasty decisions lead people to regret at leisure.
Similar Expressions: Repent at length / Suffer haste
46. Look back with regret
Definition: To review your life choices and feel sorrow over certain mistakes.
Used in a Sentence: He vowed to study hard so he would not look back with regret later. / She tried to live kindly so she would never look back with regret.
Similar Expressions: Reflect sorrowfully / Review the past
47. Beat yourself up
Definition: To blame and criticize yourself excessively for a past mistake.
Used in a Sentence: Making a mistake on the test is normal, so do not beat yourself up over it. / He tended to beat himself up whenever he forgot a minor chore.
Similar Expressions: Over-criticize / Blame self
48. A lingering doubt
Definition: A persistent feeling of uncertainty and regret about a past decision.
Used in a Sentence: Even after buying the shoes, she had a lingering doubt about whether she liked them. / He carried a lingering doubt about his exam answers.
Similar Expressions: Persistent worry / Unresolved regret
49. Wish you could swallow your words
Definition: Desperately wanting to take back something hurtful or silly you said.
Used in a Sentence: The moment the insult left his lips, he wished he could swallow his words. / She wanted to swallow her words after realizing her joke sounded mean.
Similar Expressions: Regret speaking / Take back talk
50. A regretful sigh
Definition: An audible expression of sorrow regarding a past choice or loss.
Used in a Sentence: He let out a regretful sigh as he put the unsold cookies back into the box. / She gave a regretful sigh when looking at the rainy window on field trip day.
Similar Expressions: Sorrowful breath / Sad exhale
Exercise to Practice
- Dropping your lunch tray is annoying, but there is no use crying over spilled milk.
- Eating your words means sitting at the kitchen table eating a bowl of crispy alphabet cereal.
- He wanted to kick himself when he realized he left his favorite jacket at the park.
- Rueing the day means planting red rose bushes in the school garden during spring.
- After bragging about how easy the video game level was, he had to eat humble pie.
- Having second thoughts means wearing two different pairs of socks on your feet to school.
- Biting your tongue means sticking your tongue out at your friend during a playground game.
- When he tripped on the stage during the school play, he wished the ground would swallow him up.
- Finding out he did not make the soccer team was a bitter pill to swallow.
- Turning back the clock means wearing a large wrist watch on your left hand upside down.
- Hindsight is twenty-twenty means wearing brand new eyeglasses with thick glass lenses in class.
- Repenting at leisure means relaxing on a comfortable sofa with a good book on Sunday.
- Buying a bike lock after his bicycle was stolen was like locking the barn door after the horse is stolen.
- If you skip practicing your piano scales, you will live to regret it during the recital.
- Not signing up for the school spelling bee turned out to be a major missed opportunity for him.
Answer Key
- True
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- False
- False
- True
- True
- False
- False
- False
- True
- True
- True
Conclusion
Learning idioms about regret helps you understand how English speakers express sorrow over past mistakes and hindsight. These colorful expressions make your storytelling much more emotional and relatable.
Try using a few of these fun phrases when describing past mix-ups or lessons learned with your friends. You will find that adding regret idioms to your vocabulary makes sharing your experiences much more engaging.
Frequently Asked Questions
What are some common idioms for regret?
Some popular idioms for regret include cry over spilled milk, kick yourself, and eat your words. People use these expressions to describe wishing they could change past choices.
Why do people use idioms to talk about regret?
Idioms turn abstract feelings of sorrow and hindsight into memorable, colorful mental pictures. They help people discuss mistakes and life lessons in a relatable, fun way.
How can I practice using these regret idioms?
You can practice these expressions by writing short stories or matching them to everyday scenarios like missed opportunities. Reviewing true and false practice statements is also a great way to check your understanding.
Are regret idioms used in casual conversation?
These expressions are frequently used in everyday casual speech, stories, and creative writing. They are widely recognized across all English-speaking regions.
Can an idiom help explain why hindsight is important?
Using phrases like hindsight is twenty-twenty or turning back the clock helps others understand the feeling of realizing mistakes later. It transforms ordinary reflections into clear, memorable imagery.
