I had this problem dated September 23, 2020.. The reason being is that IOS14 had been released causing this issue.. I have the watch series 2.. I had to pair but at the same time update it so I can't so update from the watch because it was in pairing mode.. So I had a phone IOS 13 and it worked like a charm.. Just waiting right now to update.. I hope to help a lot of users having this issue out there..
Greeefel
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