@KRYP2NITE There is a bug with trying to update your apple watch with IOS 14 or IOS 13 it will not let you. I had to get a phone with IOS12 or below (I used my old iPhone 6 plus which is at IOS 12.4.8) and it worked perfectly fine updating my Moms Apple Watch Series 3! Hope this works for you.
Thanks
Samuel Moorman
samalec1021
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Sorry @KYRP2NITE after you get it update disconnect the Apple Watch from the old device and pair it with your phone.
Thanks!
Samuel Moorman