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This is a common issue. Mine had trouble too.
1. update Watch to latest software
2. make sure Watch is connected to Wi-fi
3. let it sit for a couple of hours, it should download the speech pack
4. reboot

It should work. Mine didnt work the first 24 hours and then it finally worked!
 
Tried almost everything still doesn’t work. Can you check WiFi connection on an Apple Watch ? The new ones show cellular only or am I mistaken.
 
No, the new Watch shows Wi-Fi in the Control Center on the Watch, just Swipe up and on the Control Center, in the top left it will show a connection to your iPhone if available, Wi-Fi next in Blue Wi-Fi waves
watchos4-wifi-status-bar-icon.png
and if you have LTE, Green dots for LTE signal.

Dave
 
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