With the return of This is Us, obviously, we need to talk about one of Milo Ventimiglia’s greatest characters ever: Jess Mariano. There is a lot of debate surrounding Rory Gilmore and which man she should be with. Jess is the obviously the best choice but if for some reason you still love Logan or Dean (time to move on from Dean though), it is time to change your mind!
Jess and Rory started off as friends while she was with Dean. Dean was a great first boyfriend, we can all agree on that, but he was her first boyfriend. As she began to develop a friendship with Jess, Dean got very possessive and jealous. He was still holding onto the idea of Rory and a perfect relationship. Rory began to develop feelings for Jess though and ended up breaking up with Dean, subsequently beginning her relationship with Jess.
At the beginning of their relationship, Jess was more closed off, as was his nature of being, since both of his parents basically abandoned him, forcing him to live with Luke and bringing him to Stars Hollow (thank goodness). There were some rocky points in their relationship, mostly because Jess had some emotional baggage, which will become evident later, but for the most part, they were solid. They were adorable all throughout season three and had a lot of the same interests. They just worked together, as Lorelai says in the finale of the revival, “you just have to fit together” (she was obviously referring to Jess).
Now, Jess did not handle the end of the relationship well, which is why many people still do not like him. I understand; if I were on team Dean and never saw the value of Jess and Rory’s relationship, after seeing how he left, I would not be a fan. Adding to the fact that Dean comes back into her life shortly after ending things with Jess, along with Logan being introduced. However, Dean is more of a distraction for her and a way for her to feel better after how horribly she treated Dean at the end. Getting back together with Dean (WHILE HE WAS MARRIED TO LINDSAY) was a way for her to live the life she would have if she did not get together with Jess in the first place, which at this point, Rory was still upset about how Jess left.
As her relationship with Logan developed (I won’t go too much into detail as it would take way too long to analyze completely), Jess was no longer in the show, only as a guest star in some parts. The most important part though, was when Rory decided TO QUIT YALE (which I still do not understand) and live like Emily Gilmore. Jess comes back at a critical point in her life where she needs someone to just say it as it is, and he does just that. Not only does he get her to finally re-evaluate her life, he also becomes a PUBLISHED AUTHOR. He has grown up at this point and accomplished more than anyone could have imagined. He comes back mature with most everything figured out, ready to love Rory! Rory is in love with Logan, however, so Jess never really had a shot.
Onto the revival series, Jess was the one that suggested writing a book to Rory! He is her inspiration and stands by her throughout the process. While she ends up being pregnant with Logan’s baby, it is a clear indication of Jess and Rory ending up together. Logan is meant to be Christopher, Rory to be Lorelai and Jess to be Luke. If this was not clear, we can look at the specific details. Logan is very focused on his career and his fiancée, putting this before Rory. While he might love her, he puts everything before her, much like Lorelai and Christopher. Jess is constantly there for Rory, much like Luke is for Lorelai. The parallels are evident and it is clear that they are meant to be together.