Apple Watch Won't Update

Hi!

I have an Apple Watch Series 1 which I've had for just over 3 months, and it doesn't update. I get to the update page, and it lets me enter my password. I meet all the requirements (such as the battery, range, storage, etc.) and after that, it says "Could Not Connect To Apple Watch". It does this anytime I try it, I have tried restarting it, deleting and reinstalling the update and nothing has worked. Any help would be greatly appreciated!