‘Gilmore Girls’: Jason Stiles Was Actually Perfect For Lorelai Gilmore

Lorelai Gilmore ended up with Luke Danes in the end, just as most Gilmore Girls fans always envisioned. While Lorelai was far from a prolific dater, she did have a few love interests that stuck around for long enough to gain either approval or disapproval from fans. While viewers’ opinions on Jason Stiles are split, there are a few reasons that he was actually perfect for Lorelai

Jason Stiles was just quirky and strange enough to keep Lorelai on her toes

Lorelai had some unusual quirks, but the men she dated generally didn’t. Luke was, by all accounts, perfectly well-adjusted. While her relationship with Max Medina was intense and their breakup, seemingly traumatic for Max, he seemed pretty normal, too. Alex, who Lorelai briefly dated, was successful and didn’t seem to have any weird habits or traits. The only one who had any strange quirks was Jason.

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Jason had strange sleeping habits, odd food preferences, and he was pretty neurotic. Sure, that might not sound like a good thing, but Jason’s quirks are what made him so appealing. They absolutely kept Lorelai on her toes, and for someone like Lorelai that seemed pretty important. He was a challenge, and a challenge was a good thing for Lorelai.

Jason Stiles totally understood the world Lorelai came from

Aside from giving Lorelai a bit of a challenge, Jason and Lorelai actually had a ton in common, including their family relationships. They both came from the same type of upbringing, and the pair both had complicated relationships with their parents. Jason was even totally cool with the fact that Lorelai agreed to go on a date with him to annoy her mother, Emily Gilmore.

Chris Eigeman and Lauren Graham arrive at the "Turn the River" premiere at the Museum of Modern Art
Chris Eigeman and Lauren Graham appeared on ‘Gilmore Girls’ as Jason Stiles and Lorelai Gilmore | Jim Spellman/WireImage

Jason is, perhaps, the only person Lorelai dated who could truly understand her desire to get away from her family’s legacy. Even Christopher Hayden, who was positioned as a rebel, was more than willing to lean into his family’s wealth. Jason seemingly understood where Lorelai was coming from when it came to her family.  

Jason Stiles was ambitious in the same way Lorelai was

Jason was just as ambitious as Lorelai and in the same way. Unlike Christopher, who also came from the same social world as Lorelai, Jason was interested in shirking his family’s path and actually becoming successful in his own right. Just like Lorelai did.

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Instead of staying at his father’s company, he decided to go into business with Richard Gilmore. Sure, it didn’t work out in the end, but Jason didn’t run back to his parents. Instead, he seemed to make his own career, although fans are never clued in on how he made that happen, or where he made it happen.

Fans last saw Jason the night Lorelai and Luke finally kissed for the first time. Presumably, Jason moved on and found success and happiness elsewhere. He did show up at Richard’s wake in Gilmore Girls: A Year in the Life, proving that he was ever the gentlemen, even if he was a little quirky.