Tristin Dugray is one of Rory's at Chilton and a brief love interest of hers when she breaks up with Dean.  Tristin ends up dating Paris briefly before he left the series.

Gilmore Girls Quotes

Dean: You said 'boyfriend'.
Rory: No! I just meant boyfriend in the sense that the whole defending me thing was very boyfriendy, but only in the broadest sense of the word, which doesn't even apply at all here.

Taylor: You're not serious?
Lorelai: Not often, but just there yeah, I had some serious going.