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Kare Kano's pretty good. Memorable soundtrack (Opening, Ending, and the Inserts), good (and sometimes direct) humor, and pretty fun relationships. That said, it's Hideaki Anno directing a Romantic Comedy Shojo, which is about as weird a combination as you think it is. It has classic Gainax charm and some references to other works (well, mostly Eva).
It was my first Shoujo, and I imagine it was the show's sense of humor and music combined with its rather unique direction (which, I'd say, is its strongest characteristic) that hooked my young mind. But, because of the direction and the emphasis on comedy, the manga author pulled the plug on it. It was fun while it lasted, though.