Before leaving Stars Hollow High School, Rory met fellow schoolmate and her first boyfriend, Dean Forester. Dean gave Rory her first kiss in the episode in Doose's Market, where Dean worked for most of the series. Rory and Dean dated for most of Season 1 until Dean revealed that he is building Rory a car for their anniversary, and he tells her that he loved her. Rory reacts badly to this, stating that she needs time and this is a big step for her to take.
Dean breaks up with Rory, but she doesn't tell Lorelai why. This break, however, doesn't last long. Rory drops significant hints (like at the town meeting) that she misses Dean and really does love him, resulting in him turning up at Chilton where Rory tells him that she loves him ("Dean!" "What?!" "Stop!" "Why?!" "Because I love you, you idiot!") and they get back together. The relationship between Dean and Rory goes back to the way it was before the break up, and they are both happy.
When Luke's nephew, Jess Mariano, moves to Stars Hollow he and Rory have an instant connection. When Dean witnesses Jess getting into a physical fight at school, he begins to mistrust him because of his bad behavior, especially since he sees Jess and Rory are becoming friends. As Rory continues to get closer to Jess, she becomes more and more distant with Dean. This causes insecure feelings in Dean because he feels he's losing Rory, and he's trying to do what he can to keep her.
Once Lorelai tells him that he may need to give her space in order for her to want him, he backs off. However, he later simply states to Lorelai on her porch that he can tell Rory is into Jess. When Dean attends the 24-Hour Dance Marathon to watch Rory compete with her mother, he becomes distraught over the obvious jealously Rory is showing over Jess being with Shane. As the dance wears on, he can no longer stand by and watch it so he publicly breaks up with Rory, pointing out to both Rory and Jess that their feelings for each other are "so damn obvious."
After some time passes following their break up, Dean asks Rory if they can become friends to which she happily agrees. Dean later starts dating a girl named Lindsay Lister, who went to elementary school with Rory. Rory sees them kiss at a hockey game, and she admits to Lane that she had wished he would pine for her. She is a little confused as to how she feels about Dean moving on. As for Dean, it's clear that he still carries a torch for Rory.
Dean and Lindsay attend a party together where Dean attacks Jess when he sees that Jess made Rory cry. Some time later Dean tells Rory that he and Lindsay are engaged, and Rory expresses concern over Dean getting married so fast and so young as they're both just out of high school. Dean is angered at Rory's disapproval, but they later reconcile with Rory offering him a wedding gift.
At Dean's bachelor party, Dean drunkenly admits to Luke that he still cares deeply for Rory, and he would rather be marrying her. Luke later finds Rory and Lorelai who are about to attend Dean's wedding, and he tells them not to go. Unsure why Luke is so serious about the matter, they listen anyway, and they don't attend the wedding. At first, Dean and Lindsay have a happy marriage, but Dean remains close to Rory. He holds her as she cries out of stress from school, and he saves her from an awkward group date.
As he and Rory get closer, his marriage with Lindsay begins to fall apart. He tells Rory that Lindsay would like to move into a townhouse, and because of this, he needs to cut back on his time at the local college and work more hours to afford it. Rory later rants to Lane in the market about Lindsay working Dean so hard so she can have a townhouse instead of working herself, and Lindsay overhears the conversation. Lindsay tells Dean he can't see Rory anymore, but Dean doesn't respect her wishes.
Rory and Dean almost share a kiss when he's working at the Dragonfly Inn, but they are interrupted before it happens. However, on the night of its grand opening, Dean finds Rory collecting CDs at her house, and they end up sleeping together (Rory's first time). Not long afterwards, Lorelai returns home and sees the two hurriedly exit Rory's bedroom. Dean quickly leaves, and Rory and Lorelai get into a heated argument over Rory sleeping with a married man. The situation causes tension between Rory and her mother. Rory tries to talk about the situation with Dean the next day at Miss Patty's, but they have sex once again.
Rory later goes to lunch with her mother and grandmother, and she agrees to go to Europe with Emily so she can get away from Lorelai. While Rory is in Europe for the summer, Dean remains with his wife who is unaware her husband has been unfaithful. Before returning to the States, Rory asks her mother to deliver a letter she wrote to Dean. Her mother agrees, and hands off the letter to Dean while he's working at the market. However, Lindsay later finds the letter in Dean's jacket, and she publicly throws his belongings out their apartment window while the town watches below. Rory returns to Stars Hollow, and Lorelai tells her about the incident.
Dean and Lindsay eventually get a divorce, and Dean and Rory get into a strained relationship. Their time apart and the effects of the affair have clearly taken a toll on the couple. It doesn't help that Lorelai disapproves of the relationship, and Dean and Rory both have busy schedules. It is difficult for them to find time to see each other. Eventually, Rory and Dean plan to get together after Rory attends a party at her grandparents' house where Dean is supposed to pick her up at a certain time.
When Rory comes out to him late and tipsy, Dean breaks up with her because he realizes their lives are going in completely different directions. He leaves. As Rory softly cries, Logan Huntzberger (Rory's future boyfriend) steps in to comfort her. In his final appearance, Dean does not see Rory, but rather Luke. Dean compares his faulty relationship with Rory to Luke's with Lorelai, saying that ultimately Luke would hold Lorelai back from whatever potential she may have.
In the autumn, Dean randomly runs into Rory at Doose's Market. They've kept in touch sporadically, but haven't seen each other for a while. Dean is married with three kids and one on the way and Rory tells him about the book she's planning to write.
Rory's bracelet is a present from Dean for her 16th birthday. It becomes a symbol of their relationship, and Dean gets very upset one day when Rory is not wearing it. Rory had lost the bracelet (but did not notice until Dean points out it is missing) while having a picnic with Jess. Jess finds it and picks it up, but makes no mention of it to Rory. Lorelai, seeing Rory upset about Deans reaction to the missing bracelet, finds out that Jess has it and confronts him about it. After Dean breaks up with Rory at the dance marathon, she doesn't take it off, but it symbolically breaks in the shower.
- Jared Padalecki departed from Gilmore Girls to star as Sam in Supernatural