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When I had my 1:1 with my boss today, I told him at the end of the meeting that I would start my vacation after today. He said "Try to be relax and enjoy your vacation". I replied "Sure I will". Then he said "No. You won't. Nice try though". What did he mean by "No. You won't. Nice try though"? Was he just joking?

  • Based purely on the exchange (and not knowing more about the context or history of the conversation), it sounds to me more like he was saying that he wasn't giving you permission to go on vacation. That nice try was in reference to you pulling a fast one on him and simply telling him you were going on vacation tomorrow. Of course, if it was already a given that you were going on vacation, then the first comment makes sense. (Although I find nice try to be an odd thing to say, if it was meant that way.) – Jason Bassford Dec 15 '18 at 6:16
  • My guess. He knows your personality well enough to tell that you will never be able to relax and enjoy anything! – GEdgar Dec 15 '18 at 16:19
  • Whatever the boss may have meant was awkwardly expressed and does not illustrate any general feature of English language and usage. – jsw29 Dec 15 '18 at 16:27
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nice try M. Webster Dictionary

—usually used in an ironic way to say that an attempt at something was not very good or was not a nice thing to do

Meaning, in the limited context given in this question: Nice try though. You will not enjoy your vacation because of x!

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