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Rory Gilmore’s first boyfriend, Dean Forrester, isn’t exactly a fan favorite. At the very least, Gilmore Girls fans largely agree that he was not the one for Rory. Despite that, the couple actually dated three separate times during the show’s seven-season run. A lot happened during the breaks in their relationship. Still, their time apart was relatively short. 

Rory and Dean’s first break up didn’t even last two months 

Rory and Dean’s relationship was sweet to start. Fans were understandably heartbroken when they called it quits during season 1 after Rory refused to say “I love you” back. Instead of moving on quickly, Rory, refusing to wallow at first, eventually leaned into her feelings. Because several episodes were dedicated to Rory’s heartbreak, fans largely assumed the breakup lasted a while. It didn’t. 

In the season 1 episode, “Love, Daisies, and Troubadours,” Rory decides it’s time to head back into Doose’s Market to try to patch things up with Dean. Lane reveals that she encourages the grand gesture because Rory has been mopey for five weeks. The couple got back together a short time later. The breakup lasted less than two months. 

Rory and Dean’s second breakup lasted longer 

The couple’s second breakup wasn’t all that long-lived, either, despite both Rory and Dean being involved in other serious relationships during that time. The couple broke up in the fall of their senior year of high school. Dean hooked up with Lindsay Lister, whom he married less than a year later. Rory dated Jess Mariano before he hopped a bus out of Stars Hollow because he didn’t want to admit he wouldn’t graduate with his class. 

Dean Forrester stands at the counter of his apartment while his wife, Lindsay Lister, sists at the Kitchen table in an episode of 'Gilmore GIrls'
Dean Forrester and Lindsay LIster | Gilmore Girls/Netlfix

Dean married Lindsay in the fall of the following year. The marriage wasn’t a happy one. Dean and Rory began flirting by the spring semester and started their affair when Yale let out in May. They rekindled their actual relationship in the fall of Rory’s sophomore year, though. Despite an entire marriage occurring in the interim, Dean and Rory were broken up for a just year and a half before they began their affair. 

The final breakup was permanent

Rory and Dean were drawn to each other over and over again during their teens and early 20s. Eventually, the high school sweethearts outgrew each other. Their final breakup, which happened less than a year after they officially rekindled their relationship, stuck. 

Rory moved on to Logan Huntzberger, and Dean was neither seen nor heard from again during the original series’ run. He did pop up briefly in Gilmore Girls: A Year in the Life. By that point, Dean had very much moved on. Fans learned that he had remarried and had several children. He also left Connecticut entirely. Instead of setting down roots in the hamlet where his parents lived, he moved to Pennsylvania. 

'Gilmore Girls' actors Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in a scene from Netflix's 'A Year in the Life'
Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger | Saeed Adyani/Netflix

‘Gilmore Girls’: A Guide to Rory Gilmore and Dean Forrester’s Relationship

In the revival, Rory, once again, proved she had a hard time moving on. While she rejected Logan’s proposal at the end of the original series, she was mired in an affair with him nearly a decade later. It is assumed that Rory’s pregnancy was the result of their tryst.