Amy Sherman-Palladino may think that Rory's boyfriends and who she ends up with is "a small part of who Rory is" but the internet and Gilmore Girl fans disagree. And while she may want us to focus on things other than who Rory should end up with, that just isn’t going to happen, so let’s discuss.
Before going too far I just want to point out that Team Dean just isn’t a thing. Not even Dean is Team Dean.
Team Jess
In the original series, after Dean there was Jess. He basically broke them up and Rory went straight from one to the next. Jess was a troubled character who eventually began to grow and turned out to be a genuine person with the help of Rory. Then when Rory went off the handle and dropped out of Yale, it was Jess who brought her back to earth.
He did, however, lack good communication skills, which left Rory feeling frustrated and inadequate. But on the other hand, he reads, writes, and has published a book. What more could Rory ask for in a guy? (Maybe someone who doesn’t move across the country without saying anything.) Jess respects Rory for her values and her mind and is clearly still in love with her. Best we can tell, he’s also single and stable. And just like in the original series, he gave her the little push she needed to get her life back on track only this time it was by giving her the idea to write about her life.
Team Logan
After Jess came Logan. Logan helped Rory learn to live in the moment and branch out at the same time. He encouraged her to try new and daring things, like jumping off of things with umbrellas. Just like with Jess, Rory changed Logan, too: she got him in touch with his feelings. But their relationship started again the same way it did the first time, hooking up only this time with the added twist that he’s engaged. Once again, Rory is sleeping with someone in a committed relationship (while also cheating on her own boyfriend at the same time).
I truly believe that these two might have made it work had Logan not given her an ultimatum (did he really see that going his way?). I say might because while Logan continued to be with Rory despite his family’s strong opinions, family is so important to her that being with someone with a family like Logan’s would be more than a little difficult. On the plus side, Logan now makes his own money since having lost his trust fund which means he has matured a little more and can be responsible. Unlike Jess, Logan treated Rory like an equal and up until A Year in the Life, never cheated on anyone to be with Rory nor did he cheat on her. Logan was the most emotionally mature and honest boyfriend that Rory had.
I, for one, am torn between Jess and Logan. In the original series I was Team Logan all the way but now I’m just not so sure. And while ASP doesn't want us to focus too much on the men we can't help it because just as Rory parallels Lorelai, Jess parallels Luke, and Logan parallels Christopher and at times, Luke.
