There was a minor problem in some previous versions of the software where messages would display in the wrong order, so check your software versions again. You should have iOS 12.3.1 (or 12.3.2 for iPhone 8S) and WatchOS 5.2.1. If you need to update again do the iPhone first.
Forced reset your watch (and phone?) to clear any software glitches. Simply press and hold both the side button and Digital Crown for at least 10 seconds, then release both buttons when you see the Apple logo. The phone is a little more complicated, you have to select the correct method from If your iPhone, iPad, or iPod touch won't turn on or is frozen - Apple Support
Unpair the watch then re-pair which should reload all the software and download clean content from your iPhone.