Make sure your watch is fully charged. Make sure your wifi connection is strong. Make sure you have both wifi and Bluetooth turn on on your iPhone.
I had the same issue... restart watch and iPhone and go into iPhone and reset your network setting and restart your watch and iPhone again and try again. Repeat a bunch of times.
I have a feeling this has to do with connecting a watchOS5 while iPhone with IOS of 14. Try pairing with a iPhone that is on a lower IOS first if possible even if the device does not support the watch and afterwards restart your watch and try pairing it with your iPhone again... be patient but it does eventually connect.