I openly talk to them about it all the time.

I guess I was responding to this along with the content of your post.

I just don’t talk about it and make it a point not to. I talk about what I’m watching. I talk about that my friends have requested shows/movies on the server that I ended up enjoying as well. I never talk about what they are watching or not watching.

I’m sorry if I got the wrong impression from your comments and post, but I just got the sense that you maybe brought up with them that you were sad that your friend didn’t finish your favorite movie. If I were a friend with whom that was brought up with, I would think twice about what I pulled up on your server. That shows to me that my behavior is being watched and monitored, which isn’t a great feeling, free service provided by a friend or not. Again, sorry if that’s not the case here and you can disregard entirely, but this is just not how I talk to the friends and family about using my Jellyfin server.

Just know you might be making them uncomfortable. I’m sure they have no expectation of privacy, but don’t go out of your way to check on them, and don’t call them out on their viewing habits. I have friends whom are uncomfortable as it is using my homelab because they are afraid of being judged. I’d echo the others here, don’t spy on your users…