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In season 1 of Gilmore Girls, Lorelai Gilmore claimed to rarely date. That changed quickly, though. During the show’s seven-season run, she seriously dated a few men. Her first serious love interest is often thought to be Max Medina, Rory Gilmore’s English teacher. It was the first serious relationship for Lorelai depicted in the series, but technically, he wasn’t her very first potential love interest. Her first possible suitor was shown in the series’ second episode. She just turned him down. 

Lorelai Gilmore dated Max Medina during seasons 1 and 2 of ‘Gilmore Girls’ 

Lorelai and Max’s season 1 relationship culminated in their engagement. The couple’s romance wasn’t exactly a smooth one, though. In season 1, Max pursued Lorelai, despite her apprehension about dating one of her daughter’s teachers. The first iteration of the relationship ended when Lorelai tried to break up with Max at Chilton. The couple was caught kissing by Paris Geller, who told the entire school. 

Scott Cohen in 'Allegiance'. Prior to the role, Cohen played Max Medina on 'Gilmore Girls'
Scott Cohen | Craig Blankenhorn/NBCU Photo Bank/NBCUniversal via Getty Images

They did end things when the romance became fodder for the student body. Eventually, they reconciled. Max and Lorelai continued dating, but when Max met Luke Danes for the first time, he felt threatened. He proposed to end the argument, with Lorelai agreeing to marry him. Lorelai called off the wedding days before walking down the aisle and left with Rory Gilmore on a road trip in the early moments of season 2. Max and Lorelai had a few other run-ins before Rory graduated from Chilton. Lorelai and Rory never mentioned Max again. 

Technically, Max wasn’t Lorelai’s first love interest 

While Max was the first of Lorelai’s big loves that Gilmore Girls fans saw, he wasn’t exactly her first love interest. That distinction goes to the parent of another Chilton student. In episode 2, “The Lorelais’ First Day at Chilton,” Lorelai accompanied Rory to school but was stopped in the hallway by a fellow parent. 

Nick Chinlund attends the "The Chameleon" premiere
Nick Chinlund | Jamie McCarthy/ Getty Images

Ian Jack’s daughter, Julia, also attended Chilton, and Ian was immediately taken with Lorelai. Lorelai didn’t seem uninterested, either. Late for a meeting with the headmaster, Rory and Lorelai departed, but not before Lorelai told Ian where she worked. He showed up later to ask her out, but she declined, concerned that dating a fellow parent could be problematic for Rory. The irony was not lost on Gilmore Girls fans. 

In the end, it didn’t matter, ‘Gilmore Girls’ fans all agree she belonged with Luke Danes 

Whether Max or Ian was Lorelai’s first love seen by Gilmore Girls fans is pretty inconsequential. Lorelai was always going to end up with Luke. At least, that’s what Gilmore Girls fans always wanted. The realization of their love is the highest-ranked episode of the entire series. 


3 ‘Gilmore Girls’ Love Interests That Should Have Gotten More Airtime

Showrunner Amy Sherman-Palladino wasn’t initially sold on the idea. In fact, Luke wasn’t even originally set to play a large role in the series. Actually, Luke wasn’t even initially a man. During a chat with Entertainment Weekly, Sherman-Palladino revealed that Luke was originally a woman named Daisy. She only swapped the gender of the character to satisfy network executives. The chemistry between Lauren Graham and Scott Patterson is what drove the storyline.