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Bob worked all night: he'll sleep from 9 am to 6 pm. What expression can one employ to wish him a "good night" right before he goes to sleep?

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"Good night" will be understood, if he is heading to bed directly.

"Sleep well" or "Sleep tight" would fit better, but is more familiar. Bob's spouse might use this, but his coworkers probably wouldn't.

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    Sweet dreams... – James K Apr 20 at 20:26
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    I think "Sleep well" would probably by OK in any context. I agree that "sleep tight" or "sweet dreams" suggest a little bit of intimacy. – Ethan Bolker Apr 20 at 21:03
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    Good Night is perfectly fine here. In this case "night" isn't meant to indicate a time of day, but rather indicates the customary activity of most people during the night, which in Bob's case will be done at a different time of day. Night in this case just acts a synonym for sleep and that will be understood by most people. – Tonny Apr 21 at 9:43
  • Sleep well, would be my choice too. It doesn't come over as too familiar. No more so than "have a good evening/holiday" - you're acknowledging they will sleep, that's all. – Stilez Apr 23 at 6:56
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First thing that came to mind was good rest, or have a good rest.

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    I have often wished my tech co-workers "Goodnight" or "Happy Sleep" at dawn. Biological time rules, clock time does not. – waltinator Apr 21 at 15:15
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    Another common phrasing might be "Get some rest". – V2Blast Apr 22 at 19:45
  • Good rest t'you, merry gentleman! – leftaroundabout Apr 22 at 22:40
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When I was on a team that sometimes was called upon to work well into the night, coworkers often bid one another farewell with "Good work" (meaning, work is done) or "Rest well" (meaning, I'm not telling you must go to sleep now).

When we were feeling ill-used, folks might say a snarky: "Enjoy your time off" (as if being allowed to sleep after a long work shift were a vacation).

"I'll see you when I see you" was also heard, meaning the person should rest and relax, and not hurry back to work.

Direct references to sleep, bed, etc., are often avoided in business settings, as they are intimate subjects.

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Sweet dreams

Sleep tight (The origin of this strange phrase is that in medieval times beds were wooden frames with ropes across them. To stop the ropes stretching too quickly, you would de-tension them when you woke up and re-tension them at bed time.)

Not Good rest or good sleep. Not in Britain anyway. That's very clunky.

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    I would never tell my boss or coworkers “sweet dreams” or “sleep tight”. That’s far too familiar. I think it’s fine for family members or close friends. – ColleenV Apr 22 at 20:05
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As someone who does have an irregular sleep schedule due to sleep disorder, I simply use myself (and also have been wished) "good night" and "good morning" regardless of the time of day. After all, I'm not taking just a nap, I'm having my "full night's sleep", even if it's noon outside the window. And my morning is when I wake up from that sleep, I go do my morning routines and everything else associated with morning.

I also use time dependent words like "breakfast", "lunch" and "dinner" relative to when I woke up. So my first meal is breakfast, next lunch and then dinner. So I may be eating lunch at midnight for instance.

However, whenever I'm interacting with the general public, I use the normal greeting for that time of day.

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You could perfectly say good rest or good sleep.

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