A Brief History of Rory Gilmore's Love Life on Gilmore Girls
Over the course of Gilmore Girls, we fell for the loves of Rory Gilmore’s life just as hard as she did. We watched high school Rory swoon over nice guy Dean Forester before making a hard swerve and crushing on his polar opposite, bad boy Jess Mariano. Later, we watched college Rory take on her first real grown-up relationship with Yale’s suavest playboy, Logan Huntzberger.
While the Dean, Jess, and Logan trio dominated Rory’s romantic arc during our time with the Gilmores, there were a few other potential paramours worth noting in Rory’s life, too (Tristan and Marty, we're looking at you). Despite the fact that she never dated them, the guys' feelings for Rory had key impacts on her other relationships. So before Gilmore Girls: A Year in the Life hits Netflix on Nov. 25 and we find out who Alexis Bledel's character is (or isn’t) involved with these days, scroll down for our full but brief analysis of the youngest Gilmore’s romantic past.
Dean Forester (played by Jared Padalecki) was Rory’s first real crush, and despite the fact that they never officially dated while attending the same school, they were total high school sweethearts. He was the all-around wholesome boy who worked at Doose’s Market in Stars Hollow and treated Rory like a total princess. Of course, most importantly, Rory’s mom and BFF, Lorelai, liked him. On their three-month anniversary, Dean told Rory that he loved her (to which she unforgettably replied, “thank you”), and he revealed that he was building her a car as a gift. It was all too much too soon for Rory, but really, there was nothing not to love about Dean. They got back together soon after, but when Luke’s nephew, Jess Mariano, moved to town, he came between the couple and they were never truly the same again. They split for good due to Dean’s jealousy and Rory’s clear interest in Jess, but remained friends even during the short-lived time that she and Jess were an official item. Dean ultimately married another girl from Stars Hollow, Lindsay Lister, but when he and Rory reconnected after her first year at Yale, they began having an affair. Rory even lost her virginity to Dean, which felt somewhat fitting (he was her first love, after all) but so wrong (he was married to another woman) at the same time. Their rekindled flame soon burned out, for good. Really, we always knew that Rory was destined for big things—and it never quite seemed like the good-natured Dean would be the one by her side in the long run.
Tristan Dugray (played by Chad Michael Murray) was Chilton’s resident smartass who teased Rory and called her “Mary” as his way of flirting with her. While his sarcasm and good looks were certainly appreciated (a pre-One Tree Hill Murray in a prep school uniform? Yes, please.), Tristan’s attempts to win Rory over were ultimately in vain. They did share one kiss during a classmate’s party, but it was just a rebound reaction to their respective recent breakups. Of course, poor Paris was always into Tristan—and even though Rory tried to set them up, Tristan wasn’t into her—he was all about Rory, and who knows what would have happened if he hadn’t moved away for military school so early on in the series? In the end, Rory went right back to Dean, and Tristan was all but forgotten.
Oh, Jess—where to begin? Jess Mariano (played by Milo Ventimiglia) was the bad boy, leather-jacket-wearing nephew of Luke Danes. When Jess’s mom could no longer handle his behavior, she sent him to live with Uncle Luke in Stars Hollow. Although he wasn’t pleased with his new small-town life, Jess quickly warmed up to Rory. The two shared an interest in books, sarcasm, and each other. The only problem? Rory was still with Dean. After the pair got in a car accident that landed Rory in the hospital with a broken arm, Luke sent Jess back to his mother. Rory ran after him to New York just to say goodbye (we still can’t believe he left without giving her so much as an explanation). Then, after what felt like a lifetime, Jess returned on the day of Sookie and Jackson’s wedding. Despite the fact that Rory was still with Dean, she kissed Jess for the first time, and we swooned majorly. During their subsequent relationship, Jess’s jealousy over Rory’s continued friendship with Dean proved to be too much to handle, in addition to his lack of communication skills. After telling Luke that he’s done with school, Jess moved to California to live with his dad. He later returned to Stars Hollow a few times and even visited Rory at Yale because he was visibly still in love with her, but they never got back together. We didn’t see him again until years later, when he visited Rory to give her a copy of his recently-published book. She was already with her college boyfriend, Logan, but Jess gave Rory the reality check she needed by encouraging her to get her life back on track after she had left Yale and was pretty much free-falling. Months later, Rory met up with Jess again at an event for his book. She had just found out that Logan cheated on her, and she kissed Jess to make herself feel better about it—but Rory quickly realized it was a mistake and that she was in love with Logan, after all.
During Rory’s first years at Yale, Marty (played by Wayne Wilcox) seemed to be nothing more than a blip on her romantic radar. And, really, that’s all he was. Rory didn’t consider him to be anything more than a friend, just a nice guy she met during her first days at Yale. She awkwardly found him passed out, naked, in the dorm hallway—and in her mind, that’s where he always platonically remained, in many ways. But Marty wanted more, and he finally let Rory know that once she began showing interest in Logan, who Marty introduced her to, but despised nonetheless. Rory turned him down, and we all but forgot about poor old Marty until season seven, when he reappeared as the new boyfriend of Rory’s friend Lucy. Marty was totally sketchy when seeing Rory again for the first time, pretending that they’d never met before. Rory was freaked out, but she played along for a bit—until Logan ultimately blew their cover, admitting that Marty was the one who, in fact, introduced him to Rory. A betrayed Lucy broke up with Marty once his lies were revealed and it became clear that he never really got over Rory.
Was there ever a smoother talker than Logan Huntzberger? The wealthy playboy (played by Matt Czuchry) with a powerful father seemed like he’d never settle down when Rory first met him, but he soon grew on her—and us. They kept things casual at first, but were a full-on couple in no time. Logan inspired Rory, or “Ace,” as he called her, to take chances and live life to the fullest—sometimes, of course, that landed her in trouble (really, though—why did she ever think it was a good idea to steal a yacht?). Through it all, Logan was there to support Rory through her ups and downs. They eventually moved in together, and even kept the romance alive long-distance when Logan moved to London for work. He was ready to spend the rest of his life by Rory’s side, but unfortunately for Logan, Rory wasn’t quite ready for forever just yet—and at her Yale graduation, she turned down his marriage proposal, leaving Logan (and us) brokenhearted.