Rory Gilmore and Dean Forrester were not meant to be. Gilmore Girls fans largely agree that the high school sweethearts were not supposed to last forever. Still, the relationship was important in Rory Gilmore’s life. Let’s review everything that happened between Rory and Dean.
Dean and Rory started dating when they were 16
Dean Forrester might have been the new kid in Stars Hollow, but he didn’t waste any time finding a girlfriend. Dean and Rory met in the hallways of Stars Hollow High School moments before Rory transferred to Chilton. Despite not attending the same school, Dean pursued Rory, and the duo officially became a couple on Rory’s 16th birthday.
The romance lasted three months before Dean told Rory that he loved her. She did not say it back. They broke up, but the breakup didn’t last long. The couple got back together in the spring and remained together for another year. Despite reconnecting, the relationship wasn’t exactly smooth sailing. Jess Mariano, Luke Danes’ nephew, created plenty of drama and was partially responsible for the couple’s second breakup.
A lot happened between Rory and Dean’s breakups
Dean and Rory had a bit of drama in their long-term relationship, but not too much. If you think about it, the high school couple was actually pretty stable until season 3, when Rory’s interest in Jess Mariano became nearly impossible to hide. Dean broke up with Rory in front of the town at the 24-Hour Dance Marathon. While Rory acted upset initially, she almost immediately began dating Jess.
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Dean eventually moved on, too. He started dating Lindsay Lister in the middle of his senior year of high school. The pair married just months after graduating from high school. That seemed like it would be the end of things, but it was not. Dean and Rory engaged in a mild flirtation all through season 4. It eventually spiraled out of control, leading to Rory losing her virginity to Dean in the season 4 finale, “Raincoats and Recipes.” Dean was still married to Lindsay at the time. The affair led to Dean and Lindsay’s divorce.
The final breakup happened in season 5
In season 5 of Gilmore Girls, Dean and Rory reunited after their brief affair. The relationship never seemed comfortable, though. Dean seemed to think he didn’t belong in Rory’s world, and Rory seemed to find it difficult to juggle school and a relationship with a man with multiple jobs. No one in the couple’s lives made it easy, either. Dean’s mom and Lorelai Gilmore made it awkward, and Luke Danes was downright hostile about the rekindled romance. Richard and Emily Gilmore hosted a round of speed dating in response to news that Rory and Dean were back together. Rory and Dean broke up for a final time in Richard and Emily’s driveway while Logan Huntzberger and the Life and Death Brigade looked on.
From there, Dean Forrester largely disappeared from Stars Hollow. While we don’t know exactly where he went after dumping Rory for a third time, we know that wherever he went, he found love again. When we reconnected with Dean in Gilmore Girls: A Year in the Life, he had left Stars Hollow behind and was living in Scranton, Pennsylvania, with his wife, Jenny, and their three kids. They were also expecting another baby.
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