Why not use a tab system?
Make them all Flex, and then you can align the tabs menu to the right and the tabs content to the left. Also make the tabs stack vertically.
Inside of each tab link, you can costumize the text, put your play icon, the video duration, whatever you want…
Inside of each tab content, put the specific youtube video.
I believe this is want you want and it’s very simple to do.
@Velocity If you’re using a CMS, and want to be able to separate and order your Courses and Lessons, I’ve found using a Nav Bar element works even better. I’m working on a tutorial now, it’s accessible and should have all the important bits in the next few days.