Milo Ventimiglia has been teasing us for months about Jess' role on the Gilmore Girls revival, sharing just the smallest of details that have us trying to guess what he's up to in Stars Hollow. The actor has said that he'll be in three out of the four upcoming 90-minute episodes on Netflix. He's also said Jess "is up to Jess sh*t" and that's he's "kind of doing his own thing and has zero tolerance for anything — or anyone." Which doesn't make him sound like he's in a great place for dating. While so many fans have been trying to figure out how Rory and Jess get back together in the revival, it seems Ventimiglia may have just revealed something that could make the members of Team Jess a little wary about his love affair with Rory. At the same time, his revelation could mean Jess leaves a big stamp on Rory's life.
In an interview with E!, Ventimiglia explained that Jess "pops back into Stars Hollow and he kicks up dirt like he always does in a very nice cloud that will help other characters along in their life." So, while this could mean Jess helps Rory see that she's really meant to be with him, it could be something much less lovey-dovey and a whole lot more practical.
Jess has always been a catalyst for change, especially when it comes to Rory. His original appearance in Stars Hollow had him kicking up some dirt on Rory and Dean's relationship. Jess being around made Rory, albeit rather slowly, think about what she wanted in her love life and how it maybe wasn't Dean. It made her realize that breaking up is hard to do, especially when the guy you're dating isn't necessarily a bad guy — just not the right guy.
It seems like any time Jess pops into town he forces Rory to reevaluate what she's doing, even if it's in some very small way. When he comes back to Stars Hollow in Season 4 after running away to New York without even letting Rory, his girlfriend at the time, know, he tells her he loves her. While she doesn't feel the same way — something she makes clear episodes later when Jess comes to Yale to ask her to run away with him — he does force her to make decisions. To act swiftly, despite the fact that Rory is someone who makes pro and con lists, not spontaneous decisions. With him, Rory didn't second-guess herself, but did what she felt was right for herself without immediately worrying about the consequences.
Jess has always helped the levelheaded Rory take a step forward. It's him, not Lorelai, that gets her to realize she needs to go back to Yale after dropping out. While Rory always inspired Jess to do more — something he tells her when he shows up at her grandparents' house with his first published novella — it's he who gets her back to see that she's no longer the person he knew. Even more important, he gets her to see that she's no longer the person she knew. Jess returns the favor of Rory's unwavering support, not because he's looking for something, but because he understands her. This is always the reason given for why Rory and Jess are really meant to be, but it may just reveal that the two are better as friends. A very Dawson and Joey sort of relationship. This may not mean he ends up with Rory, but helps Rory figure out where she needs to end up: back on tracks with her career.
Jess being someone who sparks some positive change in the new episodes is something Ventimiglia has alluded to before. Ventimiglia talked about Jess' penchant for rubbing people the wrong way and how that could be helpful in the Netflix-era of Gilmore Girls. "He's also there to kind of push the ball forward for some folks at Stars Hollow," Ventimiglia told fans at Wizard World Comic Con in Portland back in February. "Which is what Jess has always done, whether intentionally, maliciously, or positively. He's always sent people in a direction."
Ventimiglia capped that off in his latest interview for E! saying that the revival is "classic Gilmore. It's back to the originals," a hint that may reveal more than anything that this show is about two women, a mother and daughter, trying to make it. Rory's goal was never to fall in love and get married, but to be a foreign correspondent. Jess may understand that more than anyone, which may be why he isn't trying to get Rory back into his arms. Maybe instead, he's trying to push her back out into the world of journalism to fulfill the dream she had so many years ago.
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