The second fictional character I have ever fallen in love with.

The first was Holden Caulfield, so you know where my mind's at:

Bring on the tasty, underachieving prep school boys!

Max Fischer's best friend was Dirk Calloway (nee Dennis the Menace, but don't hold it against him). He was tight with Herman Blume (friends in high places). He failed everything.

He was a barber's son.

He gave out his extension number at school to chicks whom he was trying to score.

Glasses, neatly styled hair, blazer, velvet suit. An oval face.