Apple Watch Gen 1

I have a Series 1 Apple Watch that I'm trying to pair, but I am getting a notification saying I need to first update the watch to finish pairing. I am able to initially pair the watch and start the update, but it then tells me that the watch must be connected to Wi-Fi and charged to 50% in order to update. The issue is that, without the update, the watch disconnects from its charger before reaching 50% and I am unable to connect to Wi-Fi (no menu access without first pairing).

So, without updating I cannot connect to Wi-Fi and charge, but without connecting to Wi-Fi and charging, I cannot update.

Is there a way to bypass the update to access a watch settings menu and connect to Wi-Fi, charge the watch, then update?

I have scheduled an appoitment at the Apple store and they simply said that my charger is the problem, I have purchased a new one from their store, did not solve the problem, meaning that the problem is not the charger.