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Is there a word that describes someone who continually tries something but always fails? This isn't describing in the positive sense - as in someone who never gives up - but more about the negative side of always failing.

Examples would be someone who creates many failing businesses, someone who can never stick to a diet or someone who cannot remain faithful to their partner.

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More context would help narrow down the possible words that might fit for this person. Why do they fail? Are they aiming too high and can't attain the skillset needed to achieve success? Are they lazy? Do they lack the intestinal fortitude to follow through on a goal? All of these scenarios conjure different words to describe such a failure. – Kristina Lopez

I'll give you an exact example to narrow it down more: A person who tries to diet and exercise but they always cave in and eat unhealthy stuff and/or skip exercise, despite knowing it'll be bad for them. Someone who's perfectly capable of doing it, has a sound mind and knowledge of why and how they should do it, but regardless, still fail each time they start doing it after a short while. I'm not talking about an unlucky person or a person who's too stupid or naive to achieve it.

However, I don't want the word to be specific to dieting (like "fatty" :P) but a word that could be used in other (albeit similar) contexts too. Hope that clears it up.

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    More context would help narrow down the possible words that might fit for this person. Why do they fail? Are they aiming too high and can't attain the skillset needed to achieve success? Are they lazy? Do they lack the intestinal fortitude to follow through on a goal? All of these scenarios conjure different words to describe such a failure. – Kristina Lopez Jun 3 '13 at 0:04
  • "Winners never quit, and quitters never win, but those who never win and never quit are idiots", as someone once said. – AakashM Jun 3 '13 at 9:23
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The word you are looking for is SYSYPHEAN. Although rarely used it refers to the legend of Sysyphus, a man punished by the gods by attempting to roll a rock up a hill. No matter how he tried, the rock would roll back down the hill and he would be forced to start over. Used in a sentence it would be; Joe's many attempts at a business were sysyphean since they inevitably failed.

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  • I like this very much! – Leonard Challis Feb 29 '16 at 22:15
  • The question asks for an adjective to be applied to a person, whereas Sisyphean is applied to a task. But since it was accepted, it must match the OP's intention, though not the literal statement of the question. – Robert Furber Oct 14 '17 at 15:34
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A few suggestions:

Loser. Literally someone who loses, but commonly used in a derogatory sense for someone who simply can't do anything right.

Schlemiel. Taken from Yiddish. A hapless person, one who always makes a mess of things.

Klutz. Also from Yiddish, meaning a clumsy person, a person prone to accidents and mishaps, so this would be a somewhat specialized case of what you are looking for.

Schlemazel. Yiddish again. An unlucky person; a habitual failure.

Bonehead. One who is lacking in cleverness; someone who can't "get a clue."

Failure. The literal representation of what you are looking for. A person who always fails.

Incompetent. Used in the noun form; one who has no ability to accomplish something.

And from a previous generation: Sad sack. This was the name of a cartoon character created in World War Two, and it became a term for the kind of person you are trying to characterize. Here's the definition found in The Free Dictionary (online): An inept person who makes mistakes despite good intentions.

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    +1 for schlemazel - exactly the word that I thought of when reading the Q – sq33G Jun 3 '13 at 8:08
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I think of a bungler as a person who messes up pretty much everything he or she works on or touches.

n. One who bungles; a clumsy, awkward workman; one who performs without skill.

n. Someone who makes mistakes because of incompetence

To bungle is defined as:

To work or act in a clumsy, awkward, or blundering manner.

To make or mend clumsily; botch; manage awkwardly or blunderingly; perform inefficiently.

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  • I really liked the answer with all the Yiddish, but "Bungler" got my upvote. – TecBrat Jun 4 '13 at 1:34
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Born loser 1: a person or thing that loses especially consistently 2: a person who is incompetent or unable to succeed; also : something doomed to fail or disappoint

That's actually Merriam-Webster's definition of "loser", which I think has an even more negative connotation. A "born" loser just naturally fails at everything, while losers probably got that way through their own poor decisions. That's strictly my take, mind you.

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screwup : one who hopelessly causes errors by ineptitude, carelessness, or mismanagement.

She's a screwup who can't hold down a job.

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Weak-willed

"lacking strength of will" describes perfectly a person who "caves in" to temptation.

Quote from OP's question:

Someone who's perfectly capable of doing it, has a sound mind and knowledge of why and how they should do it, but regardless, still fail each time they start doing it after a short while

From the free dictionary I found this excerpt:

Weak-willed, cowed parents continually cave in to "pester power," giving their spoilt kids anything they want, from junk food and sweets to tellies in their bedrooms.

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The Free Dictionary defines underdog as one at a disadvantage and expected to lose; nonstarter, unsuccessful person, loser, failure - a person with a record of failing; someone who loses consistently

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  • I think just failure is pretty succinct – mungflesh Jan 9 '19 at 15:04
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I like hapless. Schlemiel also good. Check out quixotic for a slightly different sense. (Virtually every browser now has built in "lookup" feature", so you'll excuse me for not including definitions...not efficient to reproduce entire dictionary on SE.)

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    It's really helpful to include word definitions with your answer to give a little background and context for the word choices - particularly foreign words, like "Schlemiel". See @JLG's answer for an excellent example. :-) – Kristina Lopez Jun 2 '13 at 23:52
  • Shlemiel carries the connotation of "makes his own bad luck"; Schlemazel is more hapless. – sq33G Jun 3 '13 at 8:09

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