When someone says damned if you do, damned if you don’t, they mean that you will be criticized no matter what you do. The idiom describes a situation you can’t win; whatever option you choose will be considered the wrong one.
Origin of “Damned if You Do, Damned if You Don’t”
This phrase is historically attributed to 19th-century Protestant revivalist preachers, including Lorenzo Dow, Edward Sprague, and Charles Grandison Finney. However, because variations of the rhyme appeared frequently in print across the 1800s, it was likely a popular critique of paradoxical theology rather than the work of a single author:
“You can and you can’t,
You shall and you shan’t,
You will and you won’t,
And you will be damned if you do,
And you will be damned if you don’t.”
The Theological Contradiction Behind the Phrase
Most 19th-century writings citing this sequence were sharp critiques of conflicting doctrines preached during the Second Great Awakening, specifically the theological trap regarding repentance.
In a religious context, true repentance is not merely feeling sorry; it requires a conscious, ongoing effort to change one’s behavior. To repent, a person must actively examine their conduct, identify future temptations, and make a deliberate attempt to avoid repeating their sins. In short, repentance inherently requires “trying.”
However, certain revivalist preachers taught that simply “trying” or “attempting” to repent was a sin of human pride; an attempt to save oneself through personal effort rather than immediately surrendering to God’s grace. Preachers instructed congregants that they must not try to repent; they must simply do it instantly.
This created an inescapable logical paradox for the believer:
- If you “try” to repent: You commit a sin by relying on human effort and striving.
- If you “don’t try” to repent: You commit a sin by remaining in unrepentant behavior.
By demanding an action that fundamentally requires effort, while simultaneously condemning the effort itself, preachers left their congregations in a zero-sum dilemma: damned if you do, damned if you don’t. Over time, the phrase broke free from its theological roots to describe any unwinnable, catch-22 situation in everyday life.
Sentence Examples
“America is expected to come to the aid of every country but whenever it does, it is criticized for interfering. We’re damned if we do, damned if we don’t.”
“NOTHING in recent years epitomises foreign policy’s “damned if you do, damned if you don’t” dilemma more bloodily than Syria.” — The Economist, May 18, 2013
“But it’s also a damned if you do, damned if you don’t situation, especially for women: they are shunned if they have surgery, and shunned if they show any signs of aging.” — The Guardian, July 11, 2016
“Germans aren’t used to being kicked in the shins by those who are also shaking the tin cup, and yet as their American allies could tell them, this is the price of leadership: it’s damned if you do, damned if you don’t.” — The New York Times, March 17, 2012
Similar and Related Idioms
- Catch-22: A paradoxical situation from which an individual cannot escape because of contradictory rules or conditions (e.g., needing experience to get a job, but needing a job to get experience).
- Hobson’s Choice: An illusion of choice where a person is offered only one option, leaving them with the binary decision to either accept the single thing being offered or take nothing at all
- No-win Situation: A scenario where every available choice or possible outcome leads to an unfavorable, negative result.
- Double Bind: A psychological predicament in which a person receives two contradictory or conflicting messages, making it impossible to satisfy either demand without failing the other.
- Vicious Circle: An unbroken chain of events where the reaction to a problem causes an effect which intensifies the cause of the problem and makes it worse so that the problem repeats and the process starts over again.
- Between a Rock and a Hard Place: Forced to choose between two equally difficult, unpleasant, or hazardous options.
- On the Horns of a Dilemma: Facing a difficult decision between two equally undesirable choices, where accepting either “horn” leads to trouble.
- Caught Between the Devil and the Deep Blue Sea: rapped in a perilous situation with an equal danger awaiting on either side; forced to choose between two dreadful alternatives.
See also the related idiom I’ll be Damned (and I’ll be Damned If I…)