Dean Forester was Rory's first love and the one she compared every future boyfriend to throughout Gilmore Girls. At the start of their relationship, Dean was charismatic, well-read, and endearing. He admired Rory's dedication to Harvard and assured Lorelai that if Rory didn't go to her dream school it wasn't because of him. But somewhere down the line, Dean became jealous and possessive with Rory, which made her pull away until the two broke up.
During Rory and Dean's dark days, a lot went wrong in Rory's life (as is the case for most on-screen teenage relationships). Rory became busy walking on eggshells, straining her relationship with her grandparents, and struggling with school during her time with Dean.
She Wasn't Doing Enough Extra-Curriculars
In "Hammers and Veils," Rory spent an afternoon building homes for the needy when she became aware of how little she was doing to prepare for Harvard. On-site, Paris told Rory that she's been volunteering her time for the community since she was a kid because it looks better on college applications. Rory realized she wasn't doing enough because she spent most of her free time with Dean. When she came home from work, she canceled her plans with him, which spiraled into a fight between the couple.
A Rift Between Her Grandparents Began Because of Dean
When Emily and Richard got to know Rory better, they wanted what was best for her — including who she dated. After hearing she was dating Dean, they invited him over for dinner in
"Sadie, Sadie." However, it became clear that Dean wasn't up to Richard and Emily's standards.
Richard, in particular, treated him like garbage, and the teens left in a tizzy. This interaction was the start of Rory's issues with her grandparents. The same thing happened years later when Dean showed up at the Gilmore residence and her grandparents invited single Yale students for a party. Rory's life took a tumble in both instances.
The Beginning Of Her White Lies
Rory isn't a bad person for telling white lies. After all, Lorelai was the queen of them, and it's something that teenagers do. When Rory began dating Dean, she wasn't always comfortable sharing her raw emotions with Lorelai or Dean. With her mom, she wasn't at ease telling her the ins and outs of her relationship and she lied to her about her feelings (especially when Jess came into the picture). With Dean, she began lying to him when she was afraid of his outbursts (like when she lost the bracelet). Rory was a standup girl who didn't lie often but it was sad when she did.
Drama At School
School is Rory's happy place. It's where she can unwind and lose herself through books. That peaceful place, however, was partially tainted by Dean. Because of his rift with Tristan, Rory's life became more stressful whenever Dean and Tristan were in close proximity.
The school dance was a particularly low point, but the drama didn't stop at Chilton. When Jess came into the picture, the two got into a chest-thumping contest in Stars Hollow over Rory's honor.
...And She Missed Curfew
Speaking of Rory's first dance... the dance at Chilton started off well enough but it took a dark turn. Once Dean found out that Tristan had a crush on Rory, the two got physical. Rory is not a confrontational person and left the dance with Dean immediately to escape any more drama — but it didn't stop there. She and Dean left Chilton and fell asleep at Miss Patty's without telling Lorelai. What's worse, Emily spent the night at Lorelai's and saw that Rory never came home. She assumed that Rory was going down the same path as a teenage Lorelai.
An Embarrassing Night With Friends
Rory's friendship with Jess was a disaster when she was dating Dean. Her white lies and tiptoeing were at an all-time high during this stage. But in "There's the Rub," Rory was at a loss when Paris and Jess showed up at her home unexpectedly. Rory knew Dean would be mad because a.) it's Jess but b.) she told Dean she was alone all night. The three friends ended up having a great night full of food and conversation, but it was ruined when Dean made a surprise arrival. Rory should have known it was over once he started dictating who she could hang out with.
An Affair To Remember
Rory and Dean's affair was one of their lowest moments as a pair. Rory's world sunk around her when this occurred. Not only did she sleep with a married man but she lost her virginity to him. To make matters worse, her mom walked in shortly after it happened and judged Rory for her actions. There Rory was — in an affair with her ex-boyfriend and in a dispute with her mom. When Dean's wife, Lindsay, found out about the affair she kicked him out and made a scene in front of the whole town. Stars Hollow soon found out about Rory and Dean's secret.
She Lost The Dance Marathon Because Of His Jealousy
While the dance marathon wasn't a big deal in "Let the Games Begin," it was for Lorelai. It was something she really wanted to do and needed Rory as her partner. The two danced the night away and were so close to winning it all, but Rory and Dean's relationship ruined it.
To be fair to Dean, Rory was outwardly jealous of Jess and Shane. It was obvious that Rory had a crush on him, so Dean made a scene over the obvious and broke up with Rory in the middle of the dance floor. As Rory stopped dancing, she and Lorelai were kicked out of the marathon.
Did Rory Become A Lesser Student?
It's hard to know what kind of student Rory would have been without Dean around. With Dean, she was able to apply to Harvard and Yale and get into both universities. She was clearly doing something right. However, when they first began talking in the pilot, she admitted to Lorelai that she didn't want to go Chilton. She wanted to stay at a mediocre school as long as it meant more time with Dean. And while she did end up going to Chilton, it's hard not to imagine that she held back elsewhere in life to be with Dean.