So,
After much research and countless back and forth with apple care, going into the Apple store and research online. Apple's new software will not be compatible with older iWatch Gen. 1 & 2. So, to answer your question, you will need a iPhone running on IOS 13 in order to update, reset and pair to the IOS phone running 13 first. Unpair iWatch from the IOS 13 iPhone and then pair to your iPhone running on IOS 14. It will ask to pair, then prompt to update iWatch. I'm currently waiting for the software to download from my iPhone. Hope this helps.
Neekodidt
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