Each time I load up a video and start it, it’s still paused for my friend and I have to ask everytime if the video is playing on his side. Sometimes it works, most of the times it doesn’t start for him.
Which browser is your friend using? It could be that he/she disabled the autoplay permission for this site. To check that: While on Watch2Gether, click on the lock icon next to the URL bar and check the autoplay permission setting.