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26 May 2017

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Question about English (US)

I often see English speakers use 'I guess' at the end when they say something.
But, sometimes, it sounds weird.
For example, "My sister took it, I guess", in this case, "I guess" makes sense but
"Well, may the best man win, I guess." How about this? This is from a movie.
Does it sound natural to English speakers?
"May the best man win" is an optative sentence, right? In this, does "I guess" mean something different?
I'd like to hear an opinion on this from a native speaker.

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