On Gilmore Girls, Marty and Rory became friends in their first year at Yale. He was one of the first people she met on campus and a tight bond quickly formed. Marty was one of the only guy friends that Rory had whom she didn't fall in love with. But on the flip side, Marty's crush on Rory grew with every semester.

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As time went on, things became complicated in their relationship but it was a healthy friendship while it lasted. As is the case for every friendship, Rory and Marty had their ups and downs but they had more good moments than bad before it all came tumbling down.

Best: Snacks & Movies

Alexis Bledel as Rory and Wayne Wilcox as Marty in Gilmore Girls

In "Jews and Chinese Food," Rory wanted to make up for lost time with Marty, so she invited him over for their usual takeout food and movie nights. Marty was reluctant to hang out with Rory because of his crush on her but did it anyway. For a brief moment, it was like old times. He even said he missed their apartment after watching one of Paris's meltdowns. Rory and Marty had a great time eating "pretzels of the world" and watching movies. That is until Logan showed up...

Worst: He Lied About Knowing Her

lucy and Marty at a bar in gilmore girls

The worst thing Marty has ever done to Rory is lying about knowing her. In the seventh season, Rory ran into Marty again when she became friends with his girlfriend Lucy.

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When Lucy introduced Marty to Rory, Rory was ready to greet him like old friends but Marty said it was nice to meet her and acted as they had never met before. It had to be one of the most awkward moments at Yale.

Best: "Naked Guy"

Marty saying he'll be known as "the naked guy" at Yale on Gilmore Girls

After meeting briefly in class, Rory finds a naked Marty sleeping outside of her dorm room. Rory woke him up to see if he needed help and the two shockingly hit it off. She gave him her robe to cover up with, which oddly broke down that awkward wall between strangers. Later, this encounter would help them become closer when he saw her walk into the dining hall in her pajamas and invited her to join him and his friends. He figured that since she saved him from an embarrassing situation, he could save her from the same thing.

Worst: The Night Out With Logan Was Awful

Marty and Rory talking in the library on Gilmore Girls

When Marty's crush on Rory grew, he tried distancing himself from her so that he could get over her. But Rory didn't allow that to happen. In one episode, Rory and Marty were hanging out when Logan interrupted and invited her to dinner.

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He ended up extending the invitation to Marty, which was incredibly awkward. At dinner, Marty realized he couldn't pay for his meal, which ended in a very uncomfortable conversation. Luckily for him, Rory was able to pay for him but it was basically the end of their friendship.

Best: He Helped Her Look For The Chilton Student

Gilmore girls - marty meets anna from gilmore girls

In season 5, Headmaster Charleston asked Rory if a Chilton student named Anna was able to shadow her for a weekend at Yale. Rory was excited to show a fellow Chilton student the wonders of Yale and what a great university it was. However, the tour didn't go as Rory and Anna expected. Anna was more interested in partying and meeting men while Rory was trying to be a parent. When Anna escaped Rory's care, Marty helped her explore Yale and beyond to bring Anna home. He was a true gentleman.

Worst: Lucy's Birthday Party Crossed The Line

Rory talking to Lucy at her birthday party on gilmore girls

At Lucy's 2000s themed birthday party, Marty did what he did best at college parties: bartend. Rory was avoiding him throughout the night after he pretended not to know her but she eventually got the courage to approach him.

She told him that she wanted things to be normal between them and that there was no need to have any tension. Marty loosened up and the two seemed to be in a good place. Shockingly, a few hours later Marty got drunk and told Rory that she was "as beautiful as ever," which made Rory very uncomfortable.

Best: The Harvard Vs. Yale Game

Marty and Rory standing outside at a Yale football game on Gilmore Girls

Rory didn't realize what a big deal the Harvard vs. Yale football game was until her grandparents bought season tickets. They invited her to the game, which prompted Lorelai to attend as well.

At the game, Rory was having an awkward time with her grandparents. Luckily for her, Marty swooped in and saved the day. He got her out of her comfort zone and invited her to a party with kids their own age. It was fun to see Little Miss Perfect, Rory Gilmore, escape her grandparents for a party.

Worst: He Turned On Her As Soon As He Realized She Didn't Like Him Back

Marty and Rory on the couch eating pizza on Gilmore Girls

One of the saddest parts about their friendship is that as soon as Marty admitted to Rory that he had a crush on her, he dropped her. She asked him if they were still friends and he agreed they were but things were never the same after that. Rory and Marty both lost each other after that night.

Best: He Filled The Void When Rory Didn't Have Lorelai

Marty gets Rory a coffee at Yale on Gilmore Girls

The void Marty was filling for Lorelai's absence was obvious to viewers but unknown to Marty. Marty did everything with Rory that Lorelai usually did. They drank coffee together, they studied together, they snacked together, and they had movie nights together. To Marty, he was having quality time with his friend and crush. But for Rory, she was doing the things she always did with her mom. Seeing her so happy and content with someone other than her mom was comforting.

Worst: He Called Her Naive And Annoying

Marty called lorelai annoying on gilmore girls

Rory isn't the easiest person to get along with but Marty let his mixed feelings for her overcome him. When the topic of Logan and his crew was brought up, Rory acted like she didn't know why he aggravated her so much. For Marty, it was obvious that it was because she had a crush on Logan, but she wasn't ready to admit it. He called her naive and annoying when she continued talking about Logan, which caught Rory off guard. As frustrating as her nativity can be, she didn't deserve his sudden tongue lashing.

NEXT: Gilmore Girls: 10 Saddest Things About Logan