Rory and Logan began dating in season 5 after initially meeting in one of Yale's many courtyards. They had ties to the Yale Daily News and the fact that his parents knew Rory's grandparents in high society. After Rory and Logan tried keeping their relationship light-hearted, Rory realized she was the commitment type. From then on, their adventurous romance was in full swing.
Logan is the last boyfriend Gilmore Girls sees Rory with. They were together throughout college and later in life when he moved to London. However, the two were anything but perfect. Rory's life has never been simple but the inclusion of Logan Huntzberger made everything dramatic, unhinged, and resulted some of the hardest years of her life.
She Was Arrested
When fans of the series met Rory Gilmore in the first season, she did not seem like the kind of gal who would get arrested. She followed the rules, listened to her mom, and was an upstanding citizen in Stars Hollow. Rory was smart enough to know better than to get into criminal activity.
Yet, the moment Logan's father tells her she's not good enough to be a journalist, she loses all sense of identity and begs Logan to steal a yacht. Sure, Logan didn't force Rory to do anything bad but if she never dated him, she wouldn't have ever met Mitchum. And if she never met Mitchum, she wouldn't have had a meltdown and stole a yacht.
She Dropped Out Of Yale
After Rory got arrested, she realized she couldn't show her face at Yale. She wasn't ready. She wanted to take time off from school because she couldn't handle the pressure. While her mother was completely against this decision, Logan encouraged it.
When has Rory Gilmore ever loathed going to school or reading books? Why would she want to be stuck at her grandmother's house planning DAR meetings instead of going to one of the most prestigious universities in the country? Not only did Logan get her into this mess but he encouraged Rory to stay in it.
She Got Kicked Out Of The Pool House
When Rory was taking time off from Yale, she moved into her grandparents' pool house for the time being. However, Richard and Emily quickly realized what a horrible mistake they made when Rory sat around all day and had no purpose in life. Where did her drive go?
Once the Gilmores realized that Logan was spending the night over in their pool house — and that Rory and he were intimate —the jig was up. They moved her out of the pool house and into the main home. This small move tore Rory apart because she realized she wasn't as independent as she thought she was.
Drunk Tears
Rory isn't used to not getting her way. Whatever she wants, she typically gets. But when Logan wasn't ready to commit to her, Rory lost herself. She drank far too much Founder's Day punch and cried in her mother's lap on the bathroom floor.
While everyone on Gilmore Girls has had their heart broken once or twice, it was out of character for the down-to-earth Rory Gilmore to be crying on the bathroom floor over a boy.
A Rift With Lucy
It was incredibly odd when Marty pretended not to know Rory when he was dating Lucy. Marty and Rory never dated, so why would there be secrecy? They were once great friends — this is something Lucy would have loved. Instead, Marty treated Rory like she was a stranger. Rory was going to tell Lucy about the strange connection with Marty on her own time, but Logan decided to do it instead. While at dinner, he told Lucy everything. Lucy was mortified and left the table. Logan's abrupt message created a huge rift between Lucy and Rory because Rory didn't get to tell her herself.
She Turned Down A Solid Job In Hopes Of Something Better
When Rory was nearing graduation from Yale, she applied for different jobs and fellowships at small and large papers. She found out she was offered the job at a smaller paper in Providence. With the help of Lorelai and Logan, she went through the pros and cons of taking the job versus waiting for the fellowship.
Lorelai told Rory she should take the job; she needed security. Logan, on the other hand, told Rory to turn down the job and take a risk with the fellowship. This caused a major tone-deaf conversation between Lorelai and Logan. Instead of listening to her mom, Rory followed Logan's advice and turned down the job. And unsurprisingly, she wasn't offered the fellowship. She was now back at zero.
The Demise Of Lorelai & Rory
If Rory never started dating Logan, she wouldn't have been arrested, dropped out of school, and wouldn't have been living in her grandparents' pool house. Lorelai and Rory never fought as hard as they did when Rory began dating Logan. Logan never forced Rory to do anything she was uncomfortable with but he clearly inspired her to live fearlessly — maybe a little too much. With Logan by her side, Rory and Lorelai's rift was deep.
Kissing At The Vow Renewal Created A Fight Between Luke & Christopher
The problem with Rory is that she never thinks her choices have an effect on anyone else's life. While at her grandparents' vow renewal, Rory thought it was the perfect opportunity to lure Logan out of the reception to drink champagne in the back room. The two were gone so long that her mother had to come looking for her.
What started as a steamy makeout session turned into a war between Lorelai and Christopher, and Lorelai and Luke. All three adults were protective over Rory and a fight broke out. Luke ended up breaking up with Lorelai, Lorelai scolded Christopher and kicked him out of her life, and she cut ties with her mom.
Her Confidence Went Down The Drain
One of the most inspiring things about Rory is how confident and all-knowing she was at such a young age. She's a great listener, logical, and she ignores drama when it comes her way. But once she started dating Logan, Rory unraveled.
After having dinner with Logan's entire family, Rory heard for the first time that she wasn't good enough. She was taken aback because her last name was Gilmore, and things only got worst from there. Fans of the show had never seen Rory so confused and insecure than her time at Yale with Logan.
Entitlement And Privilege
As much as Rory wants to pretend that she's not in the same privileged circle as Logan and his friends, she's lying to herself. She found herself in a bit of trouble when she wrote an article judging the very people Logan hung out with, which meant that she was also judging him.
What Rory failed to realize was she was just as privileged. She attended private school, went to an Ivy League university, she never had to work, and her grandparents were multi-millionaires. Rory lost who she was when she was with Logan, and her article proved that.