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While leaving office at 6pm, I wonder if I shall say 'good evening' or 'good night' to my boss.
Since night is far off, 'good night' sounds odd. But then, 'good evening' has a welcoming tone to it, as if I am entering office and not leaving.

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    Normally, you would say good evening when you greet someone at night, and good night when you leave them at night. Good evening is also used as a dismissal. – Robusto Jun 23 '17 at 4:29
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    Use "good evening". While it is the end of the work day, there are still things to do (drive home, eat dinner, watch TV, take a bath, ???) before going to sleep. "good night" is better when you are done doing other things for the day. If you went to a party after work, and it ended at 10PM, it would be more likely to use "good night". – user3169 Jun 23 '17 at 5:14
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    If you feel comfortable with neither, "See you tomorrow" also works. But I'll cast another vote for "good evening." – aschultz Jun 23 '17 at 9:14
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    @user3169- I liked your question marks.:) – Ramit Jun 23 '17 at 16:02
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Since you've mentioned that it's only 6pm then "Good evening" is your choice, it means "expressing good wishes on meeting or parting during the evening.". However, "good evening" by itself is considered more of a greeting rather than a farewell so I recommend saying "Have a good evening" instead.

You could also say something like "Goodbye and good evening to you".

We usually say "Good night" when the time is for a normal person to sleep, like 9-6pm for instance. "Good night" often means "I'm off to bed"; it's "an expression of farewell used in parting at nighttime or when going to sleep". However, you wouldn't use that phrase in the daylight.

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    Could you provide contemporary examples with good evening in which the sense of farewell is clear? – userr2684291 Jun 23 '17 at 11:31
  • @userr2684291 Unfortunately, only "Have a good evening" is practically used a farewell. I'm unaware though whether you can say "good afternoon" to say goodbye after 6pm. – SovereignSun Jun 23 '17 at 11:44

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