Can't add music to my watch

I have personal music files installed on my iphone and they play fine with the phone. When I use the watch app and go to the music section and try to add a playlist to the watch to download, all of the songs in the playlist are greyed out and they won't load to the watch. It keeps saying can't connect to apple watch, make sure it's nearby and not in airplane mode, which it is not. Any ideas? I have already tried erasing all content and settings and the watch is running the latest software