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Lorelai Gilmore (Lauren Graham) had a handful of love interests on Gilmore Girls before ultimately ending up with Luke Danes (Scott Patterson). Among them was her daughter’s English teacher at Chilton, Max Medina (Scott Cohen). 

Alexis Bledel and Lauren Graham at the 2006 Summer Television Critics Association Press Tour for the CW
Alexis Bledel and Lauren Graham at the 2006 Summer Television Critics Association Press Tour for the CW | Kevin Winter/Getty Images

Their romance began during the TV show’s early episodes while viewers waited for the day  Lorelai would face her feelings about Luke. Long before that happened in season 4 when Luke and Lorelai kissed, Rory Gilmore’s (Alexis Bledel) mom became engaged to Max. But their relationship was never going to last. 

Lorelai Gilmore kept forgetting to give Max Medina a key to her house

With their wedding fast approaching Lorelai and Max had their respective bachelorette and bachelor parties. Thanks to a touching story about her mother’s own wedding, Lorelai realized Max wasn’t the guy for her. 

The next day she and Max had an argument about keys. Specifically, the fact that Lorelai kept forgetting to give him a spare key to her and Rory’s house. Less than a week before their wedding, Max wondered aloud whether or not Lorelai actually wanted him there. 

Lorelai Gilmore didn’t see Max Medina as a parental figure

After their double date with Rory and her then-boyfriend, Dean Forester (Jared Padalecki), Max didn’t know how to handle the two teens being alone together. He immediately asked Lorelai about his role in her daughter’s life. 

Lorelai said not to worry because Rory’s already grown up and that if it came to disciplining she’d handle it. Max took that as him having no authority in the Gilmore household as a parental figure to Rory. 

Max Medina and Lorelai Gilmore didn’t discuss where they’d live

With Max and Lorelai’s wedding date getting nearer and nearer, Luke asked Lorelai some questions. Lorelai answered “I don’t know” to nearly every question Luke threw at her, making her realize she and her fiancé didn’t have important things figured out. For instance, whether or not they’d make Stars Hollow their permanent home. 

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Lorelai told Max something about knowing the location of the coupon drawer upon her death — a nod to Luke’s comment about his dad not knowing where his deceased mother kept the coupons — and that she wanted to figure out major details about their lives together.

Lorelai Gilmore felt weird about Max Medina sleeping in her house

Lorelai couldn’t get used to Max being part of her life. Case in point, she felt weird with him sleeping in her bed.

She couldn’t sleep and found herself wandering downstairs to Rory’s room. Lorelai told Rory the situation weirded her out but the half-asleep teen didn’t see it as a sign that she wasn’t ready to marry Max. 

Ultimately, Lorelai didn’t go through with the wedding and went on a road trip to Harvard with Rory. 

Watch Gilmore Girls and Gilmore Girls: A Year in the Life on Netflix.

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