There's no question about it — one of the biggest questions [1] that Gilmore Girls [2] fans have for Netflix's reboot, A Year in the Life [3], is who Rory Gilmore might end up with [4] and whether it might be someone from her past. The question calls to mind all the significant relationships in Rory's life, and boy, has the youngest Gilmore had some doozies. Before the reboot premieres on Netflix on Nov. 25, let's take a look at Rory's five biggest relationships.
Dean Forester
- Appears in: Seasons one, two, three, four, five
- Dates Rory during: Seasons one, two, three, five
- Their relationship: Dean is a sweet, genuine, and loyal boyfriend — and he's nuts about Rory. Unfortunately, there isn't much to him beyond that, and after a while they start to grow apart. The problems are only exacerbated by the fact that Rory develops a serious thing for Jess. Their breakup in season three is painful and dramatic, but it seems inevitable.
- Why he's important: You never forget your first love, and Dean will always be the perfect example of the perfect first boyfriend. Dean also teaches Rory that simply wanting a relationship to work because it sounds nice doesn't mean it will. Sleeping with him at the end of season four while he is married is a HUGE no-no. And even though Dean ends his marriage and tries to make it work with Rory again, it just isn't meant to be.
Tristan Dugray
- Appears in: Seasons one, two
- Dates Rory during: N/A
- Their relationship: Oh, Tristan. So spoiled, so obnoxious. He's private school snobbery in human form. Tristan doesn't quite know what to make of Rory — the shy, brilliant new girl at Chilton who seems immune to his smarmy charms — and that's what hooks him. Tristan can't have her, so he wants her even more.
- Why he's important: At heart Tristan isn't a bad guy, just a product of his privileged environment. He's also at the mercy of his parents, who take him out of Chilton in season two and send him to military school. In the end, he's the kind of guy who we all know would be exactly wrong for Rory — but their dynamic also shows the audience that Rory won't simply be swept off her feet by any guy who smiles at her.
Jess Mariano
- Appears in: Seasons two, three, four, six
- Dates Rory during: Season three
- Their relationship: The big one. Jess Mariano is reckless, irresponsible, and impulsive when he arrives in Stars Hollow in season two and is generally pretty rude to almost everyone in town except Rory herself. Honestly, that would be hard for any girl to resist. Once Rory and Jess actually start dating, she comes to realize that Jess is just too angsty and closed off to make a real relationship work. And come on, leaving town for California and not even telling Rory? That's cold.
- Why he's important: Jess is wrong for Rory in many ways at the time she dates him. But he then matures into someone who could be just right . . . just at the wrong time. By the time Jess gets his act together and gets back in contact with Rory in season four, she's on her way to getting back together with Dean. And then when they meet again in season six, she's with Logan. Jess is Rory's ultimate "what if?" guy, and that's what makes him so intriguing.
Marty
- Appears in: Seasons four, five, seven
- Dates Rory during: N/A
- Their relationship: Poor Marty just has bad timing. He arrives in Rory's life when she really needs a friend in college more than a boyfriend (especially after the sting of Jess disappearing from her life). And when she's ready for a relationship again, Dean is back in the picture. By the time THAT falls apart, Logan's already on the scene.
- Why he's important: Marty is honestly a very sweet guy; he simply gets stuck in the friend zone. He's Rory's first real close male friend, and their relationship goes the way that so many male-female friendships do. When the truth about how Marty feels about Rory finally comes out (and she admits her feelings for Logan), their friendship is over. He shows up in the final season, but their friendship never gets back on track. You're sorely missed, Naked Guy.
Logan Huntzberger
- Appears in: Seasons five, six, seven
- Dates Rory during: Seasons five, six, seven
- Their relationship: Logan Huntzberger is the dream: the playboy who reforms his ways when he meets the one girl he just can't live without. He's perhaps the most unlikely long-term relationship for Rory — she can't stand him when she first meets him. We can't really blame her; Logan's privileged, spoiled, and arrogant . . . he just also happens to be a lot of fun.
- Why the relationship is important: Throughout their (rather tumultuous) relationship, both Rory and Logan do a lot of growing up. They're very different people, but they always come back to the conclusion that they care about each other too much to call it quits. By the time Gilmore Girls [9] ended, Logan had himself a stable career and was ready to marry Rory. But his proposal is what shows Rory that she needs to pursue her own dreams before settling down. She chooses to live her own life in her own way over being with the guy she loves, and that's gutsy.