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I'm looking for a word that means

someone (especially a boss) who is not pleased (with your work, attitude etc.) no matter how hard you try.

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Do you mean a word that describes this type of sentence, or a word that might have this sentence as its definition? –  KitFox Jun 23 '11 at 15:14
    
A word that can replace this sentence. For example I want to use it like this: 'You are the most '<word>' boss I have every worked with. –  SidCool Jun 23 '11 at 15:16
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I cant resist: a$$hole is usually what I would use –  JoseK Jun 23 '11 at 15:20
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Haha, that may cost me my job :) –  SidCool Jun 23 '11 at 15:53
    
I found another word 'intractable' –  SidCool Jun 24 '11 at 16:39
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10 Answers

up vote 17 down vote accepted

Dear boss,

You are the most implacable boss I have ever worked with. You are pitiless and immovable no matter how hard I try.

For these reasons, I'm out.

Yours sincerely...

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+1 Implacable is a nice word. Very classy. –  KitFox Jun 23 '11 at 15:25
    
Indeed. Of the ways to quit, this is the classiest. –  Adriano Varoli Piazza Jun 23 '11 at 15:29
    
+1 for implacable. –  Marthaª Jun 23 '11 at 15:38
    
I like the word 'implacable'. I am going to go with it. But does it sound refined and intellectual? I want to sound smart without offending her (oh shit, I spilled the beans ;)) Implacable is almost perfect, thanks! –  SidCool Jun 23 '11 at 15:54
    
Yes, that's why I changed my display name :) You opened my eyes –  SidCool Jun 23 '11 at 16:40
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"Unpleasable" seems to be what you're looking for. Examples: TvTropes for Unpleasable Fanbase. Etymology at dictionary.com.

While not rude per se, the implication of the word is that there's no way around it. This person is not "hard to please". It's plain impossible to please this person. I'd say it's not rude but harsh to tell a boss he's unpleasable.

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I am not sure if that's a word. Is there a more refined word? Unpleasable sounds downright rude. –  SidCool Jun 23 '11 at 15:14
    
Rude? It literally means "that cannot be pleased". –  Adriano Varoli Piazza Jun 23 '11 at 15:16
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@SidCool: you dont want it to be rude - are you preparing for an annual performance review meeting? :) –  JoseK Jun 23 '11 at 15:22
    
From your other comments: if you had to tell this to your boss, the last thing I'd do if I wanted to patch things with him is concentrate the message on one word. If you wanted to quit, on the other hand, go right ahead :) –  Adriano Varoli Piazza Jun 23 '11 at 15:26
    
@JoseK - You are close :) –  SidCool Jun 23 '11 at 15:55
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I think persnickety is a good word to use here. It means "overly particular" or "fussy" and has the added benefit of sounding like it might not be insulting.

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Either the boss knows what the word means, and he feels a bit insulted, or he doesn't, and feels ignorant (and insulted 10 minutes later when he checks it). I don't see it as an advantage. –  Adriano Varoli Piazza Jun 23 '11 at 15:27
    
@Adriano So it's doubly insulting. That could be an advantage. –  KitFox Jun 23 '11 at 15:29
    
well yes. But not going by what @SidCool is telling me... –  Adriano Varoli Piazza Jun 23 '11 at 15:30
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picky

petty

nitpicker

quibbler

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These aren't bad, but to me, the question didn't ask for "hard to please", but for "impossible to please". –  Adriano Varoli Piazza Jun 23 '11 at 15:33
    
I agree with @Adriano. –  SidCool Jun 23 '11 at 15:55
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  • difficult

Or (with a nod to The Shawshank Redemption):

  • How can you be so obtuse?
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Ah, but remember how well using "obtuse" worked out for him! No, thank you... –  MT_Head Jun 24 '11 at 0:59
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Oh ho! I have an idea. Most of the words suggested so far definitely sound negative, which is to be expected, because it is a negative thing to be difficult to please.

How about particular?

"She is very particular in her preferences."

To say that a person is particular means that he has exacting expectations. A person may take that as a compliment if they agree and do not feel they are being mocked. I would happily admit that in my writing I am very particular about my choice of words. If somebody said that I was very particular about the meals I was served, it wouldn't seem quite so complimentary. The word is a little more elastic in its connotation.

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Hypercritical is the quality of always finding fault and never being pleased.

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Fastidious might be the word for someone who is very hard to please.

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Thanks for the answer! It's already received a downvote though, so you might want to improve it by adding a link to a definition to support the answer. I've noticed that the OED definition doesn't support your answer (oxforddictionaries.com/definition/english/fastidious), but others might. –  toryan Aug 26 '13 at 10:08
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I think fastidious can suit well?

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Placare in Italian means to calm someone down, to make amends, to soothe. Look the English definition up, and there's no mention of a person who is never satisfied or pleased. To please, in Italian, is contentare So, although the term, implacable, is indeed classy and sounds refined, technically, it's incorrect.

In my view, the most appropriate word is: dicontenting (very rare) or malcontented: A chronically dissatisfied person

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