Tristan and Rory meet when Rory starts Chilton, and he instantly starts teasing and toying with her, which Rory finds at first bewildering and, as time passes, offensive and annoying. Rory is convinced that Tristan teases her because he is flirtatious by nature and keeps it up because she's not interested, but it turns out that Tristan actually has feelings for Rory. Oblivious to this, Rory strikes up a friendship with Tristan, who wants more but is unsuccessful due to Rory's feelings for Dean. Though Rory sometimes seems like she could be interested, their connection is also complicated by Paris feelings for Tristan. Before Tristan gets in trouble and is sent to miliatary school, he and Rory end on good terms.
On Rory's first day at Chilton, Tristan walks in and is immediately attracted to Rory. He makes a move on her in his typical douche fashion, assuming she's a doe-eyed girl, who will find him interesting, but is surprised to soon learn that she doesn't find his ways enchanting. This only makes Tristan pursue an obnoxious behaviour toward Rory, both teasing and being mean to her, while also continuing flirtation. Rory doesn't think this means that Tristan truly likes her, rather that he's trying to prove that he can get any girl he sets his sights on, but his altercation with Dean at the Chilton dance is the first time she considers otherwise.
Following Rory's break-up with Dean, she attends a party at Madeline's just in time to witness Summer dumping Tristan, and the two share common ground, Tristan being vulnerable and kind to Rory for the first time. He kisses her and she kisses back, but is heartbroken over Dean and leaves Tristan. Rory initiates a conversation about their ensuing awkwardness and insists that the two should be friends, which Tristan hesitantly accepts.