Tristan goes to Chilton with Rory and Paris. He unsuccessfully tries to get Rory to date him and obnoxiously calls her Mary, as in the Virgin Mary, a practice common, but dated in catholic/private schools. Paris, on the other hand, has a crush on him and is jealous of the attention he gives Rory.
Tristan tells Rory that he wants to take her to the dance but she doesn't believe he is sincere, since he is mean to her. He watches Dean kiss Rory and is obviously jealous, going off to make out with his date as a distraction. Dean and Tristan get into a "fight" over Rory. Dean later tells Rory that Tristan has a thing for her. Paris and Tristan have been in the same classes since kindergarten, and he kissed her, on a dare, in sixth grade. Paris also hints he's had a hard life, and his parents weren't that great, like hers.
After breaking up with his girlfriend, Summer, Tristan sulks in a room alone during Madeleine's party. Rory stumbles into the room and they end up comforting each other over breakups. Rory and Tristan share a moment and end up kissing. However, Rory becomes upset because of her recent breakup with Dean.
Upon Rory's advice that he date someone with "a little more substance", Tristan takes Paris on a date. However, when an angry Paris blames Rory for the date not being anything more, Rory confronts Tristan leading to him asking her, "Is it fair that I date her even though I like someone else?". Hinting he has a crush on Rory. Rory naively thinks he is referring to his ex-girlfriend Summer and is confused by his exasperation.
He gets 2 tickets to PJ Harvey and invites Rory to go with him, but she declines saying, "It wouldn't be a good idea for us to go together. It would seem too much of a date." He says, "It would be a date." After Rory leaves, Paris sees the tickets and asks who's going with him and he replies Rory. Rory finds out and goes straight to Tristan. Dean comes to school and Rory tells him she loves him.
In season two, Tristan's father sends him to military school after he, Duncan and Bowman break into Bowman's dad's safe and the silent alarm 'kicks in'.
Summer and Tristan dated for several weeks, possibly a couple of months. The two were once seen making out so intensely that neither of them noticed Rory or Paris' pleas for them to move from their lockers. At Madeline's party, Tristan got into a fight with Summer. Summer and a Chilton student named Austin were locked in a bathroom together, making Tristan suspicious and angry. He tried to talk to her, but she was concentrated on partying with other guys. Eventually, he got her to talk to him, but that unfortunately caused her to break up with him. Tristan was briefly depressed and humiliated by the breakup, which caused him to sulk alone in Madeline's piano room. He then kissed Rory who cried.
Tristan had kissed her years ago on a dare causing her to have a crush on him. Paris consistently admired Tristan and dreamed that he would ask her on a date. Rory suggested that he date someone with "a little more substance", after his breakup with Summer. Tristan took Paris on a date. Paris mentioned to Rory that he kissed her goodnight, making her think that he wanted to date more. The two had a good time, but unlike Paris, Tristan only thought of her as a friend. He then stupidly mentioned how it was Rory's idea to Paris, angering Paris.
- Main article: Tristan and Rory
Despite treating Rory rudely and calling her names, Tristan had a gigantic crush on her. It is hinted that he teases her because he's accustomed to getting any girl he wants and is further intrigued by Rory as she doesn't fall for his charms right away. Thus, Tristan gives Rory a lot of attention, angering Paris who harboured a crush on him since childhood, sparking tension between Rory and Paris on many occasions. Despite Tristan's behavior, he is often genuine with Rory. For example, he told her his feelings about Summer, tried expressing how he felt (Rory assumed he wasn't talking about her), and seemed to listen when Rory gave him advice. He researched one of Rory's famous music groups and bought tickets, but arrogantly presented them to her, causing her to reject him. Desperate, Tristan takes Rory's books and tells her he won't give them back unless she agrees to go with him. Unfortunately for him, Rory didn't care, and ended up getting back together with Dean right in front of him.
- His character left due to Chad Michael Murray filming Dawson's Creek and One Tree Hill.
- At one point he paid a mechanic to take apart and put back together a teacher's car in the centre of one of Chilton's buildings.
- His grandfather, Janlon Dugray, does business with Rory's grandfather. At the beginning of the series Janlon is sick, but by the time Rory turns 16 he is doing much better.
- Murray was unable to reprise his role for the revival. The character was played by Days of Our Lives actor Anton Narinskiy.
- The Lorelais' First Day at Chilton • The Deer Hunters • Rory's Birthday Parties • Rory's Dance • Paris is Burning • Concert Interruptus • Star-Crossed Lovers and Other Strangers • The Breakup, Part 2 • The Third Lorelai • Love, Daisies and Troubadours • Run Away, Little Boy • Spring