Throughout Gilmore Girls’ seven seasons and a sequel series, Rory (Alexis Bledel) has experienced her fair share of romance – here’s a breakdown of all the major love interests for Rory. Gilmore Girls mostly depended on the dynamic between Rory and Lorelai (Lauren Graham), as well as their complex relationship with Lorelai’s parents, while the girls’ love lives added significant drama and development for the characters. Lorelai had a few notable love interests over the series like Rory’s father Christopher and Rory Gilmore’s teacher Max, but the overall consensus was that she and Luke Danes were meant to be, with the two eventually getting married in Gilmore Girls: A Year in the Life. On the other hand, Rory’s love life was far more complicated, with no one boyfriend being singled as the clear favorite among audiences – although, allegiances to Rory’s boyfriends are pretty widespread among the main three.
While the original series spawned the notable arguments about who was the best among Rory’s big three boyfriends, there were a few other guys who were contenders. In Rory’s first year at Chilton, she was harassed and flirted with by Tristan (Chad Michael Murray), who clearly liked her even though she was dating Dean. Once at college, Rory became close with Marty, who had a crush on her that she never reciprocated, though some fans still think he should’ve been the one she ended up with.
The original Gilmore Girls series gives Rory three main boyfriends, each of whom comes into her life at different points that influence her growth as a character. From the shy 16-year-old golden girl in Stars Hollow to the more combative reporter at Yale University, Rory was always facing some sort of relationship drama. Fans continue to go to the mattresses about who the best boyfriend was, with Gilmore Girls even introducing another significant – though barely present – boyfriend for Rory in Netflix’s Gilmore Girls: A Year in the Life revival.
Introduced in the premiere episode of Gilmore Girls, Dean Forester (played by Supernatural’s Jared Padalecki) was the new boy in Stars Hollow who quickly developed feelings for Rory. Although moving schools, Rory started to like Dean back, and he became her first kiss and, later, her first boyfriend. The duo had a brief breakup at the end of season 1 when Dean told Rory he loved her and she didn’t say it back. Dean broke up with her, but after a little bit of time, she realized how much she missed him and that she did love him, leading to a happy reunion. Rory and Dean continued to date until halfway through season 3 of Gilmore Girls, breaking up because Rory clearly had feelings for Jess Mariano. Lorelai had a soft spot for Dean being a sweet boyfriend to Rory, especially when she started dating the less outgoing or polite Jess.
Even though Dean and Rory broke up in season 3, their relationships had been falling apart ever since Jess arrived early in Gilmore Girls season 2. Dean didn’t like how combative Jess was and the two would constantly get into fights, which became worse when Rory and Jess became close friends. Dean’s jealousy was overbearing and made him overprotective and possessive of Rory, something that Lorelai pointed out and advised him to give her space. When the two go to a 24-hour dance together, Dean saw Rory being obviously jealous over Jess’s date. Dean then broke up with Rory for a second time, after which she started dating Jess.
Although Dean and Rory getting back together was never like it was before, the Gilmore Girls season 4 finale saw the two rekindle their romance while Dean was still married to Lindsay Lister. That night, Rory and Dean got together and she lost her virginity, an event worsened by Lorelai being subsequently disappointed in Rory for getting with a married man. Dean and Lindsay officially got divorced after she discovered his affair with Rory, leading Dean to start dating Rory again when she returned from Europe. With Rory in college meeting plenty of new people and being further away from Stars Hollow, the two had a strained relationship that finally ended when Dean broke up with her after realizing their lives were headed in different directions. Dean was then primarily written out of Gilmore Girls, and the two remained friends for the rest of the series.
Rory’s second boyfriend Jess Mariano (Milo Ventimiglia) is either beloved or hated by fans – there’s not much of a middle ground here. He was introduced in Gilmore Girls season 2 as Luke’s nephew, who came to live with him after getting into trouble. Jess hated Stars Hollow and particularly struck a chord with Lorelai, with Rory being one of the only people in town he really liked. Even though Rory was dating Dean, he would flirt with her and they grew to have a significant connection through their shared love of books. He and Rory shared similar intellectual fascinations and interests, and he only truly showed his soft side to her. After kissing in Gilmore Girls’ season 2 finale before Rory went to Washington D.C., the two had no contact over the summer, so she continued dating Dean. After Dean broke up with Rory because she clearly had feelings for Jess, she finally confronted Jess about her feelings and they began dating.
Jess and Rory continued to have a rocky relationship in season 3, with Jess struggling with communication and being disliked by Lorelai and Emily. After Jess discovered he wouldn’t be graduating high school, he skipped town to go see his father in California without saying goodbye to Rory. He called her and (without him speaking) she broke up with him, saying she could have loved him but she wasn’t going to pine for him any longer. Jess was then a recurring character for the remainder of the series, almost always having remnant feelings for Rory while he worked on improving himself. He later joined a publishing house and wrote a novel in Philadelphia, where Rory Gilmore realized Jess was doing better than herself and that he had his life together. Jess was the one who influenced Rory to get her life back together after dropping out of Yale, though the two never actually rekindled their relationship. Even when they were friends again in Gilmore Girls: A Year in the Life, it was clear Jess still had feelings for her nine years later, although he denied it. With how great of a person Jess became over the series, some fans have decided that his significance extended beyond the three-boyfriends fight, with some fans feeling that Rory didn’t deserve him at all.
Rory’s final major boyfriend in Gilmore Girls was Logan Huntzberger (Matt Czuchry), a troublesome wealthy peer at Yale who quickly started flirting with her. Rory initially disliked Logan because he could act cruel and arrogant as a product of his wealth and low self-esteem. After a while, Rory and Logan dated in a no-strings-attached relationship once she admitted her feelings for him, though he was hesitant to become exclusive. Logan and his friends took in Rory with a lot of warmth, which gave her a much more exciting college experience, though with a lot more rebellion and risks than Rory was known for back in Stars Hollow. After Rory decided she couldn’t be in a no-strings-attached relationship anymore, Logan decided he’s ready to date her exclusively rather than lose her halfway through Gilmore Girls season 5.
The two dated off-and-on throughout the rest of the series, with Rory even getting an internship at Logan’s father’s newspaper. Logan’s mother and grandmother disapproved of Rory being career-oriented while his father told her she’s not cut out to be a journalist, leading to several bumps in their relationship, as well as Rory dropping out of Yale University. Rory later took a break from Logan after he revealed his deep insecurities via fighting with Jess. They quickly got back together, but their relationship was strained when she found out he slept with other women while on their break.
Rory and Logan continued to date through a series of bumps, such as Logan going to South America and moving to London for work, with Logan eventually proposing to Rory in Gilmore Girls season 7. Rory declined, and they broke up because he doesn’t want to go backwards in their relationship. It’s then revealed in Gilmore Girls: A Year in the Life that even though Rory had a boyfriend and Logan was engaged, they’d been having an affair. Gilmore Girls: AYITL ended with Rory telling Lorelai she’s pregnant, and the general consensus among viewers was that Logan is the baby’s father, even though it’s never actually revealed.
The least-known boyfriend of Rory Gilmore is Paul, a man who Rory revealed in A Year in the Life that she had been dating for two years. She explained that she meant to break up with Paul, but she always forgot. Gilmore Girls seemed to deliberately make him out to be a very forgettable character, with Lorelai and Luke meeting him but never remembering their interactions. Paul eventually visited Stars Hollow in Fall and broke up with her, making him the Rory’s last official boyfriend in Gilmore Girls.
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