Max Medina was one of the first relationships viewers saw Lorelai have on Gilmore Girls. After meeting at Chilton, the two had an undeniable chemistry that they couldn’t ignore, so they decided to give their romance a try. Not long after they started dating, things took a turn between Lorelai and Max and their future together.
As great and smart as Max was, he was also incredibly clingy. He liked Lorelai so much that he became pushy and demanding, two things Lorelai didn’t appreciate or need as a single mother. It wasn't until the two became engaged that it was a slow decline until Lorelai finally called it quits.
He Wouldn’t Take No For An Answer
The connection between Lorelai and Max was abundantly clear when they met each other at Chilton. It doesn't make too much sense that Chilton didn't have rules about teachers dating parents, but they made it work. She came into his classroom like a wildfire and he was enthralled by her.
He finally asks her out at the school’s bake sale, which she was uncertain of because of his connection to the school. But his clinginess comes in full force and he persuades her to meet him for coffee. From there, their relationship begins although Lorelai was reluctant because of Rory.
The Reason He Proposed
Max and Lorelai weren’t dating for a long time before he proposed. It wasn’t until Max came over to pick Lorelai up for a date and found Luke inside that he began to panic.
Although Lorelai and Luke were just friends at this time, Max became so jealous of Luke’s intimidating presence that he proposed to her on the spot. Lorelai was taken aback by his dying need to marry her, since the two hadn’t been dating that long. It was all too much too soon.
The Extravagance Of The Second Proposal
Max didn't care that he was only Lorelai's boyfriend for a short time. He was infatuated with her. After he proposed in Lorelai’s house, she told him that was not the proper way to propose to someone and told him to, essentially, try again one day. Instead of waiting a while before proposing, Max did it the very next day.
He ordered over 1,000 yellow daisies to the Independence Inn, which covered the entire first floor. As sweet as this was, it was also a clingy moment because he proposed in such a way that Lorelai couldn’t say no. He knew this would be the talk of Stars Hollow and that she would look like the villain if she turned down such a grand gesture. It was also cowardly that he created a proposal without him there. It was almost like he couldn’t bear the humiliation of her saying no in public.
He Was Trying To Be A Father-Figure To Rory
After having a double date with Rory and Dean, Max was uncomfortable with Rory being out so late with a boy. This prompted him to have a conversation with Lorelai about his presence in the house. If they were getting married, he wanted a say in Rory’s upbringing.
His need to be a part of every aspect of Lorelai’s life threw her off because she had been independent for so many years. Once he tried taking over a parenting role, Lorelai became disinterested in the relationship.
He Wanted Rory To Call Him Max (Without Running It By Lorelai)
When Max starts coming around the house more, Rory is uncomfortable because he’s her teacher. She’s also not used to having men around the house because it’s always been just her and her mom. Max tries to break the ice and make things relaxed for Rory but his clinginess for Lorelai is too strong.
Without talking to Lorelai about it, he tells Rory that he’s going to be around a lot and that she should call him Max. Rory is clearly uncomfortable with this and isn’t ready to call her teacher by his first name and yet he insists. Rory was a good student and didn't want the distraction. The two eventually settle on a nickname but again, only because Max wishes it. The next day, Lorelai is completely bewildered with her daughter calling Max by his first name and something changed in her because of it.
He Got Rory Involved When Lorelai Ghosted Him
When Lorelai realized Rory was becoming attached to Max, she panicked. At that moment, everything was all too real for her and things would be different for her and Rory. In typical Lorelai fashion, she began to pull away from Max. With him in the dark, he had the audacity to approach Rory about the situation at school.
He asked her if Lorelai was coming to the parent-teacher conference because he hadn’t heard from her in a while. The conversation made Rory uneasy because she knew her mom was ghosting him and now she, a teenager, was involved.
He Wanted Her To Tell People That They Were Dating
In ‘P.S. I Lo..' Rory is annoyed when she finds out Lorelai and Max were dating again because Lorelai kept her out of the loop. After a small breakup, the two rekindled their romance and kept it a big secret.
When Rory ran away to her grandparents' home because of it, Max came over to console Lorelai. Because of Rory’s reaction, he asked Lorelai if she told other people that they were dating. Lorelai said no, which annoyed Max. He wanted to know why she didn’t tell anyone and why she was avoiding the conversation. It was Lorelai’s decision when she told people and she didn’t need Max pressuring her to do it.
Max’s Parents Were Pushy
When Max and Lorelai became officially engaged, they went out to dinner to talk things through. Right off the bat, he bombarded her with his parents' involvement in the wedding, claiming that they had written a check and wanted to help where they could.
As Max is talking, Lorelai orders another martini—clearly uncomfortable with the conversation—as Max tells her that she can now call his mom, mom. Not only that but Max’s mom offered Lorelai her wedding dress. The eagerness doesn’t fall far from the tree in Max's family and Lorelai loathed it.