Ouran High School Host Club (2006)

This is going to seem like an out-of-left field suggestion but it's one of my favorite animated series, let alone anime, of all time. It's only one season so it's very digestible.

The set up is Fujioka Haruhi is a special scholarship student that is attending the prestigious Ouran High School where only the most elite and rich kids attend. They do an oopsie in the first 5 minutes of the show and go into debt and must pay it off by working in the titular host club.

For a show that came out in 2006 it handles a lot of subject matter shockingly well. It never makes punch lines out of marginalized characters. A club full of rowdy, pretty boys are all actually very tender and kind and considerate. They have their character flaws but they work through it because of their friendships and understanding. There's love. It's a comedy. It's actually a parody of a lot of other host-club shows and does the thing where it both makes fun of and subverts common tropes. There's other themes of dealing with loss, abandonment, fears, societal expectations, breaking out of gender norms, mutual aid, companionship, jealousy. And it's all handled extremely delicately. I cannot recommend this show enough.