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Jonathan Hargrove Wigglesworth Bates is the director of the Winter Lake Academy for the Arts during the first five seasons of the show. He loves to watch telenovelas and eat fondue, and demands a room in any and all of his living situations exclusively for his theater memorabilia. He is wildly creative but horrendous with money.

He approaches Bonnie in episode 2.5 about an ambitious production he plans to stage, and although she is not sure whether he is really after her or her family fortune (which would help him stage the production), she accepts his proposal in episode 2.11. They elope, but the marriage, which is discovered not to be legal, disintegrates when Bonnie learns that her "late" husband Jerry is alive and looking for her and Jonathan discovers that the fading soap opera star Calliope Witherspoon is actually Callie Murphy, a girl he hooked up with on Christmas Break while she was a student at The Academy and he was a student at the Finger Lakes School For Aimless Boys. After he learns that their brief dalliance produced a daughter and the daughter has a child of her own who is herself a student in Jonathan's very own theater department, he sets off for California in search of Calliope and resigns from his job. He is replaced by Colin Andrews.

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