‘Damned if You Do and Damned If You Don’t’: Definition, Meaning and Examples

You might have heard someone use the phrase you’re ‘damned if you do and damned if you don’t.’ Are you wondering what this phrase means? Below, we’ll look at the meaning, examples, and more.

In short:

• ‘Damned if you do and damned if you don’t’ is a way for someone to say they’re in trouble no matter what.

Essentially, it means that you can’t win or that you’ll be criticized no matter what you do.

What Does ‘Damned If You Do and Damned If You Don’t Mean’?

‘Damned if you do and damned if you don’t' is an American expression that people use when they’re in a situation where they feel they can’t win. It’s a common phrase that you might hear when someone feels they’re in an impossible situation.

It might also mean that:

• In a specific situation, a person will be blamed or considered wrong no matter what they do or say.

For example:

• On your way home, you get a text from your mom saying you’re in trouble for what happened in school today. You know you’re already in trouble at home for talking back to your mom, but you got a good grade on your latest spelling test.
• In this situation, you’d be damned if you do and damned if you don’t tell your parents about the test.

You can use this phrase if you feel like you’re in a catch 22 type of situation, such as the way you need an address (apartment) to get a job and a job to get an apartment.

Another typical catch-22 people often experience in life is that to get a certain job, and you need work experience. But to get work experience, you need to have had a job.

If anyone is ever in either situation (or a similar one), they might say that:

‘I’m damned if I do and damned if I don’t.’

Where Does ‘Damned If You Do and Damned If You Don’t’ Come From?

The earliest use of the phrase ‘damned if you do and damned if you don’t’ comes from a letter that a subscriber wrote to Samuel Snowden.

• He was the publisher of the Alexandria Gazette, Commercial and Political, which was published in Alexandria, Virginia.

It was published on Thursday, February 20^th, 1817.

It read:

One says that the town was never known to be in a worse state of corruption than it now is, and it comes from the same source; that the mayor and others have been extra-prompt in the cause of morality, which perhaps is as good a way as any to account for the knowledge of the corruption. But who are they that complain most? Are they not those whose craft is most in danger? I mean that by which they have their wealth. In taking this view of the subject, it reminds me of a sermon that I once heard; the preacher was shewing the inconsistencies of those opinions which he was combatting; he observed that the preaching of the advocates of these opinions amounted to this: you will, and you wont [sic], you can, and you can't [sic], you’ll be damned if you do, you’ll be damned if you don’t. So it appears that our rulers must be served, let them do good or do bad, do right or do wrong, make good laws or bad laws, enforce them or let them be a dead letter, it is all the same, they must be damned.

The phrase was later published in Biographical Sketches of the Rev. Edward Sprague, which was published in the New Hampshire Sentinel on Friday, October 7, 1825.

Examples of ‘Damned If You Do and Damned If You Don’t’ in Sentences

How would you use ‘damned if you do and damned if you don’t’ in a sentence?

Let’s look at some examples:

• I can’t believe my dad sent me to work on a bunch of junk cars. I can’t move them, and I can’t replace the parts. I’m damned if I do and damned if I don’t.
• I really want this apartment, but I need a job. But in order to get a job, I have to have an address. I’m damned if I do and damned if I don’t.
• If I invite Stacy, Jane will be mad. But if I don’t invite Jane, she won’t bring the cake. I’m damned if I do and damned if I don’t.
• If we have the party inside, we’ll have to share the space with other people. But if we have it outside, we might get rained out. We’re damned if we do and damned if we don’t.
• My fiancé is stuck in San Diego because her flight was delayed. If I go pick her up, it’ll take too long, and we’ll lose the venue. If she takes an Uber, she might not make it on time. We’re damned if we do and damned if we don’t.
• Teachers in underfunded schools either have to work with the limited resources they’ve been given or use their own funds to get what they need for their students. But that takes away from the teacher’s already deeply underpaid salary. They’re damned if they do and damned if they don’t.
• I chose not to be a doctor because of all the debt. If you don’t come from a rich family, you either go into debt or work yourself to death (unless you want to remain living under the poverty level). You’re damned if you do and damned if you don’t.
• If you want to enjoy life, you have to make money. If you want to make money, you have to get a job. But if you have a full-time job, that makes it hard to enjoy life. You’re damned if you do and damned if you don’t.

Other Ways to Say ‘Damned If You Do and Damned If You Don’t’

What are some other words and phrases that have similar meaning to ‘damned if you do and damned if you don’t’?

Here are some examples: 

• Screwed no matter what
• Catch 22
• Pickle
• Jam
• Predicament
• Backed into a corner
• In a bind
• Quandary
• Dilemma
• Difficulty
• Between a rock and a hard place
• In a complicated situation
• Unforeseen circumstance
• Inevitably
• Up a tree
• In the snake pit
• Headache
• No-win situation
• Can't win

Final Thoughts on ‘Damned If You Do and Damned If You Don’t’

To recap, we learned:

• ‘Damned if you do and damned if you don’t’ is a way for someone to say they’re in trouble no matter what.

Essentially, it means that you can’t win or that you’ll be criticized no matter what you do.

If you ever get stuck on meaning or usage, you can always come back to review what you learned. We’ve got an entire library of content on Idioms that you might find helpful on your journey to learning English. Go check it out anytime.