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I know the general meaning of using お疲れ様です/でした to express gratitude for some work, but I'm a bit fuzzy about appropriate times to use it.

I know it is a common saying when leaving for the day, and I've also seen it in email when replying to someone who has just done some task, but are there other situations where this would be appropriate (or inappropriate)? Is there any kind of time element implied (would it sound strange in the morning?)?

Also, when is it appropriate to just use お疲れさん instead of お疲れ様?

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I'd describe it best as a greeting or set phrase used after (any sort of) work has been done. It can be used in a variety of situations:

  • at the end of any shared activity (before leaving home from work, after volunteer work, after group activities like hiking), very much in the sense of "See you..."
  • when greeting somebody who (supposedly) is working or has just finished work (coming into the office during the day, greeting your colleagues/friends/spouse after work)
  • acknowledging somebody's efforts ("I finished what you asked me for..." - "Ah, otsukaresama, arigatō gozaimasu.", "I walked 5 miles to get here." - "Otsukaresama!")
  • humorously ("I finally decided on which shoes to buy!" - "Otsukaresama desu.")

I wouldn't use it first thing in the morning when coming into the office, since everybody's (supposedly) just starting to work. I'd use it when coming back into the office from a client meeting though, for example. Using it if I just came in late because I overslept is borderline (お疲れ様って言うなよ、オマエ! ;-)).

お疲れさん or お疲れ can be used somewhat more informally than お疲れ様. Not advisable in formal situations.

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Ah, I figured my morning comment might be weird. In this particular context, I had just finished a conference call where I was dialing in from the US communicating with coworkers in Japan. It was the end of the day for me, but the start of the work day for them, so I wasn't sure if it would be strange to say お疲れ様 when we were done. –  Troyen Jun 15 '11 at 2:46
    
@Troyen If you were talking about work related stuff, you supposedly both worked during the call, so it wouldn't have been weird. If you were just chatting and were both aware of each others situation, you might've said じゃ、頑張って下さい and your Japanese colleagues could have said お疲れ様. –  deceze Jun 15 '11 at 2:49
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  • Regarding formal use:

It is a widely-held misconception (even among some young Japanese when they start working in a company) that you should use お疲れさま when leaving the office. Strictly speaking, this is incorrect.

お疲れさま[です/でした] is something you say to people leaving, or when you and the other person are both leaving (e.g. when you meet a colleague at the door etc.).

Saying お疲れさま[です/でした] when you are leaving, has a (very) slightly insulting overtone, in that you are essentially saying "I'm knackered and going home! [while you guys stay here]", which is not really the business Japanese way...

When you are leaving, it is probably more polite to say:

お先【さき】に失礼【しつれい】します: "I apologise for leaving before [you]"

Of course, there are also countless informal occasions where using any variations of お疲れ[さま][です/でした] is OK.

Mainly:

  • at the end of any strenuous activity (or even not so strenuous ones, as a joke)
  • as a less formal and more "matey" replacement for 乾杯【かんぱい】("cheers", when toasting).

PS: I don't often hear お疲れさん in daily conversations: people will tend to use either お疲れさま (without です/でした → semi-formal) or just おつかれ (very informal).

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@Dave おつかれちゃん can be heard sometimes –  Nicolas Raoul Jun 15 '11 at 8:57
    
@Nicolas: thanks for the precision. Though I was mostly addressing Troyen's original question regarding おつかれさん's use... Both are pretty rare in my experience, but this is entirely subjective. –  Dave Jun 15 '11 at 10:12
    
@Dave: I think there's something missing in both answers. My idea is: おつかれ is addressed to other people (not for yourself, because お is respectful). When you leave alone while others are still working you say "お疲れさまです" because they ARE still there. But they tell you "お疲れさまでした" because you finished your work. Does it make sense? –  repecmps Jul 3 '11 at 3:07
    
@repecmps: first off, all interpretations aside, the usage caveat I described above comes from official "on-the-job training" such as new recruits usually get... so I'm reasonably sure of it. As for the rest: while 'お' is a "honorific", it is most definitely not a self-sufficient sign of "respect" (in that you can very well use 'お'-words in situations where you are the "higher-up"). In any case, this expression projects the idea of a task being completed, and therefore using it toward people still at it, does sound a bit rude to me, but it might just be conditioning ;-) –  Dave Jul 3 '11 at 3:26
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@Dave is right on this topic. When you leave you should say お先に失礼します then they will answer you お疲れさまです, then after leaving the building the security guard will say お疲れさまでした!. When I was not familiar with this particular piece of Japanese culture I used to say お疲れ様です and leave, and then somebody nice would correct me and say "I think you meant お先に失礼します". –  wallyqs Jul 3 '11 at 4:13
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Why all the answerers, commentators and upvoters here are hung up only on the "dictionary" usages of the phrase, I have no idea. The answerers even seem to live in Japan.

In today's Japan, the phrase is OFTEN used as a casual "Hi!" as well --- if someone wants to know the fact.

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Is it a casual greeting in all situations, or are there circumstances where it would be an inappropriate or awkward choice? –  Troyen Dec 3 '13 at 2:33
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