Milo Ventimiglia’s Gilmore Girls Spinoff Never Would’ve Worked – And That’s Coming From Someone Who Was Team Jess


Jess Mariano was originally supposed to get his own Gilmore Girls spinoff, but it’s for the best that this never happened. Jess is one of the four boyfriends Rory has in Gilmore Girls, and he became a fan-favorite character almost immediately after arriving in the town of Stars Hollow. It’s probably no surprise that Luke Dane’s nephew charmed viewers nearly as much as Luke himself, even if the two characters rarely agreed on anything. While most fans concur that Dean was wrong for Rory, Team Jess remains popular — and on par with Team Logan.

With Jess being one of Gilmore Girls’ best love interests, it’s no surprise that Milo Ventimiglia’s character almost led a spinoff series. In fact, it was one of two planned Gilmore Girls spinoffs that never came to fruition. Jess’ troublesome backstory opened the door for a deeper exploration of him as an individual. He also went in an interesting direction after leaving Stars Hollow, occasionally returning to shake some sense into Rory. It’s easy to see how Jess’ spinoff could have worked, but it might be a good thing that it didn’t pan out.

Jess’ Proposed Gilmore Girls Spinoff Explained

“Here Comes The Son” Was Supposed To Be A Backdoor Pilot For Wayward Circle

Many of Jess’ “bad boy” tendencies stem from his tumultuous relationships with his parents, and in particular, his father. Gilmore Girls characterizes Jimmy Mariano as a deadbeat, but that doesn’t stop Jess from seeking out a better relationship with him. In the Gilmore Girls season 3 episode “Here Comes the Son,” Jess journeys to California to reconnect with Jimmy after a disagreement with Luke. And “Here Comes the Son” was actually supposed to be the backdoor pilot for the character’s spinoff, which would have been called Wayward Circle (via The Paley Center).

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As “Here Comes the Son” suggests, Jess’ series would have taken place in Venice Beach and focused heavily on his relationship with his dad. In this way, it would have mirrored Gilmore Girls, which also centered on a parent-child bond — albeit one in far less need of repair. And Wayward Circle wouldn’t just serve as a redemption of sorts for Jimmy. While Jess showed up less frequently on Gilmore Girls after Milo Ventimiglia left the show, his return in season 6 revealed he’d changed quite a bit. His spinoff would have shown this rather than letting his growth happen off-screen.

Why Milo Ventimiglia’s Gilmore Girls Spinoff Didn’t Happen

Milo Ventimiglia as Jess Mariano posing by the woods in Gilmore Girls

Despite Jess being a fan-favorite Gilmore Girls character, his spinoff never actually came to fruition. The WB initially green-lit six episodes of Wayward Circle, but the network decided against following through on them. This allegedly had to do with the costs of filming in Venice Beach, California, which would have made Jess’ show an expensive endeavor (via IMDb). Ventimiglia departed from Gilmore Girls after season 3, so the cancelation of Wayward Circle essentially ensured viewers wouldn’t see or hear much from Jess after this season.

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Of course, Ventimiglia still returned for a couple more Gilmore Girl appearances, which allowed him to give his character a proper resolution. Jess begged Rory to go away with him in Gilmore Girls season 4, and he convinced her to go back to Yale in season 6. The latter appearance highlighted how much Jess had matured, and it also revealed he’d written a novel. The character also showed up in Gilmore Girls: A Year in the Life, which gave all three of Rory’s major love interests a send-off.

Jess Not Getting A Gilmore Girls Spinoff Was For The Best

It Would Have Struggled To Recapture The Original Show’s Tone

Jess Mariano (Milo Ventimiglia) sits in the newspaper office in Gilmore Girls: A Year in the Life.

It’s probably for the best that Jess’ Gilmore Girls spinoff never became a reality, as it would have struggled to replicate the magic of the original series. The mother-daughter dynamic between Lorelai and Rory is the heart of Gilmore Girls, and Jess’ bond with his father likely couldn’t compare. Due to Jess’ troublesome upbringing and Jimmy’s own issues, Wayward Circle would have been a more serious show than the original. While this wouldn’t necessarily be a bad thing, it would have made it tonally different from Gilmore Girls, potentially turning some viewers off it.

Jess was undoubtedly interesting enough to explore in more depth, but the plan for Wayward Circle probably wasn’t the right way to go about it.

California would also have failed to capture the small-town charm of Stars Hollow, further removing Wayward Circle from Gilmore Girls. Jess was undoubtedly interesting enough to explore in more depth, but the plan for Wayward Circle probably wasn’t the right way to go about it. It would have been more interesting to see how he grew within the confines of Stars Hollow, fully delivering on his relationships with Luke and Rory before having him depart. Unfortunately, Ventimiglia’s departure from Gilmore Girls and the canceled spinoff made this impossible. At least we got to see what became of him later on.

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