Mom always told me, it can't hurt to ask, the worse case scenario is the answer is NO, which is what it would be if you did not ask, I don't feel you are putting anyone in a difficult position, it goes with the job, its just a simple no, sorry, not that awkward in my opinionYou're rather bold in my opinion to ask for an upgrade. You're placing the individual at check-in in a difficult position. It's one thing is you've been a long time, frequent customer who stays several times per year, but I suspect you're not. It doesn't hurt to have your "special occasion" noted in the reservation. That's the appropriate way to ask for an upgrade. At time of check-in is rude.
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