In the pilot of Gilmore Girls, Rory Gilmore is a sweet teenage girl who dreams of getting into Harvard. She's leaving her small-town high school behind when she meets new kid Dean Forester. Suddenly, she wonders if she should go to Chilton after all, which starts a big fight between her and her cool mom Lorelai.
Gilmore Girls deals with teenage life well and part of that includes Rory and Dean's relationship. From their meeting to the early days of their romance, along with their two break-ups and reunions later on in their lives, this love story is an important part of the show.
7 Season 1: The Meet-Cute, Sweet Romance, And First Break-Up
Rory and Dean meet each other in the show's first episode and they have a truly adorable scene. Rory makes a joke about Rosemary's Baby and is shocked and thrilled when Dean understands it.
After kissing at Doose's Market, which is awkward but cute, and Lorelai inviting Dean over for a movie night, Rory and Dean enter an official relationship. He's a sweet partner, making her a bracelet and always making time for her, and things seem to be going well... until he says he loves her on their three-month anniversary and she can't say it back. Suddenly Rory is single again and learning to wallow from her mom, who swears that junk food and pop culture will help her grieve the loss of Dean. But the two lovebirds make their way back to each other in a sweet scene at Chilton.
6 Season 2: Jess Makes Waves In Rory And Dean's Seemingly Perfect Love Story
In season 2 of Gilmore Girls, there are some problems in Dean and Rory's relationship, as he thinks she cares too much about Chilton and getting into Harvard. He complains about not getting enough time with her, which creates even more stress in her life.
Rory thinks their relationship is flawless, though, at least until Jess moves to town and she starts to like him, too. Jess creates major waves for Dean and Rory, flirting with Rory every chance he gets. Fans can tell that this won't end well for Dean, and it seems like nothing can stop Jess and Rory's feelings for each other.
5 Season 3: An Intense Break-Up
Dean ends his relationship with Rory during the Stars Hollow dance marathon in the third season episode "They Shoot Gilmores, Don't They?" and while it's sad, it's not a huge surprise. He's fed up with watching Jess and Rory flirt and banter and he knows that it's a lost cause to try to save his relationship.
Rory and Jess start dating immediately and by the next episode, they're stealing kisses whenever they can, which must feel super awkward for Dean since, of course, he still has to live in Stars Hollow.
4 Season 4: Rory Loses Her Virginity To Dean
Rory has sex for the first time with Dean in the season 4 episode "Raincoats and Recipes." This definitely changes their relationship as after being exes for a while, they're now in a strange place where they realize they still share an attraction and real feelings.
When Lorelai comes home, Rory shares that she lost her virginity to Dean, and Lorelai can't understand why her daughter would make that choice considering the fact that Dean is married to Lindsay. It's one of the rare times when the mother and daughter duo don't seem to see eye to eye and it's also obvious that Rory and Dean have a bond that has never really gone away.
3 Season 5: Rory And Dean Get Back Together
Rory and Dean get back together in season 5 of Gilmore Girls after Lorelai's shock that Rory would lose her virginity to someone who was married.
This love story continues to be super rocky. When Lorelai suggests a double date with Luke and Dean, she and Rory struggle with how awkward it is, and Luke is upset because he doesn't approve of Dean. After attending a Friday Night Dinner, Dean feels left out and like he can't possibly be the right person for Rory now. It's hard for Rory to balance being a Yale student and spending time with him, which echoes their high school days when he said she spent too much time studying. They break up again, and Rory starts seeing Logan.
2 Seasons 6 & 7: Officially Out Of Each Other's Lives
In seasons 6 and 7 of Gilmore Girls, Rory is all about Logan, and their relationship leads to some negative changes in her life.
Rory and Dean seem to be out of each other's lives for good. In season 6, Rory sees Jess a few times, but no one hears what Dean is up to, as his last appearance is in the fifth season. At first, it must seem like things are simpler with Logan since he's confident, fun-loving, and willing to commit to Rory, but of course, things get more complicated as Rory realizes Logan has some family problems that he tends to ignore. Logan's father Mitchum is very judgemental and demanding, and he doesn't support Rory and Logan's romance.
1 A Year In The Life: Bumping Into Each Other At Doose's Market
Rory still loves Stars Hollow as much as ever in the revival A Year In The Life, and she even bumps into Dean at Doose's Market.
This is a fitting place for them to see each other again since this was the setting of their first kiss and where Dean used to work when they began dating. The two haven't seen each other in years and have a brief conversation. Rory thanks Dean for being so sweet to her and says that their relationship was a really good thing in her life. Dean is glad to hear that but he has definitely moved way past Rory and Stars Hollow. He's married, has his own family, and doesn't seem to really think about Rory anymore.
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