

No, each server is accessed separately. You can swap between servers easily, but there is no central way to browse all of your servers simultaneously. Jellyfin was designed specifically to rebel against Plex’s centralization, so that’s not a feature they’re ever likely to implement. There are ways to sync your watch history between servers, but it’s using third-party plugins.
Yeah, dating is 100% a numbers game. You cast a broad net, and then pick through the ones who show interest. There’s no way to find the right person without failing a few times. The people that end up with their high school sweethearts are the exceptions that got extremely lucky, not the standard to strive for.
Don’t take the failure personally. Unless you’re blatantly going around cheating, being misogynistic, racist, etc., it’s likely not anything in particular that you did “wrong”. It simply means you weren’t a good match. The best thing you can do is simply be the best version of yourself. By that, I mean to avoid just sitting around on your hands, expecting someone to land in your lap. The “if you can’t handle me at my worst, you don’t deserve me at my best” mentality is extremely toxic; Be the kind of person that your ideal partner would want to date.