Rory is in Max's English class during her sophomore year, and she gets a D on her first paper for his class. When Rory misses a Shakespeare test due to tardiness, Max offers to let her do extra credit to make up for the missed test (1.04). Max asks Lorelai on a date at the Chilton bake sale (1.05), and the two begin a relationship. Lorelai ends things when she realizes how much she and Rory like having Max in their lives. Max is extremely hurt, but after the headmaster threatens to fire him for having a relationship with a Chilton parent, he decides they shouldn't be together (1.11). Several months later, Lorelai shows up at his apartment late one night, and they start seeing each other again (1.17).
Max proposes to Lorelai in the Season 1 finale, and she accepts several days later (2.01). They plan a wedding for the end of the summer, but Lorelai calls off the wedding only a few days before the wedding after realizing that she doesn't love Max (2.03). When school starts, Max and Rory are very awkward around each other; when Rory is assigned to interview Max for the school paper, they both express their regret that the wedding didn't happen (2.05).
At some point, Max goes to California to teach a class at Stanford, where he dates a woman named Diane. He returns to Hartford for the Chilton bicentennial, and he runs into Lorelai several times. Although he tells her that he is fine with how things ended, he kisses her, then admits he isn't over it (3.16). His last appearance is in (3.19), where he is on the parents' committee for the Chilton graduation party with Lorelai. She seems interested in starting a relationship again, but he insists that he wants her to stay away from him.