I have my workout app set to play one of my playlists on my Watch when I start. BUT it always starts with the same song and plays the list in the same order. How do I get it to shuffle songs?
On the music playing face, tap on the hamburger in the lower left corner and that will bring up the shuffle and repeat options. As far as I know, it’s temporary and you will have to tell it to shuffle each and every time. At least, I haven't figured out how to get it to shuffle by default.
Edit: the music playing screen doesn't offer the hamburger in the Now Playing app, it can only accessed in the actual Music app. It's a hassle but you will need to go to the music app and set it to shuffle there.