Tristan picked on Rory more than anyone else at Chilton — with the exception of Paris (Liza Weil). He started calling her "Mary" on their first day because he thought she looked like the Virgin Mary. Even when Rory screamed at him to stop in the midst of a breakdown after being hit by a deer, he didn't drop the nickname. In a rare moment at a Chilton party, Tristan showed Rory a softer side. But the notorious bad boy still got himself shipped off to military school.*

*North Carolina, where he played Lucas on One Tree Hill.