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In the following sentence

"I saw my old classmate on the first day of the vacation. That was an awkward situation, as we had never had a private conversation before."

Can I replace "awkward" with "shy" in the sentence?

My personal opinion is no. I also checked the dictionary. Please confirm if my opinion was correct. Thank you.

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The adjective "shy" is almost always used to modify conscious beings (the Oxford Pocket English Dictionary describes shy as, "nervous or timid in the company of other people"). I've never seen it used to describe anything else. It's a personality trait.

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    The mountain's height is just shy of 5km. I agree, I wouldn't use "shy" to describe the awkward situation. – Zebrafish Jul 20 '18 at 15:15
  • @Zebrafish I should've been more concise. You're right—that is also a use case of shy. – kafir Jul 20 '18 at 15:17
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    The rule of thumb can be: a person is shy and a situation is awkward. That said, a person can also be awkward (ungainly) but a situation can never be shy. "To be shy of some measurement" is a special, phrasal use of shy. It means: just under [some measurement]. It's an idiomatic expression. – Lambie Jul 20 '18 at 15:43

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