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Jason "Digger" Stiles is a fictional character on the television series Gilmore Girls, played by Chris Eigeman.

Jason, son of Carol (Catherine McGoohan) and Floyd Stiles (Lawrence Pressman), attended Camp Chatagory with Lorelai and Rory's father Christopher when they were all kids. Jason's camp nickname was "Digger," which stuck. Lorelai's nickname was "Umlauts," after she fell out of a canoe in a green t-shirt with no bra on. Luckily, that one didn't stick.

Lorelai: I can't believe you just called me Umlauts.

Jason: You called me Digger three times before I called you Umlauts once. I think that shows great self-control.

—Season 4, Ep. 6 "An Affair to Remember"

Floyd Stiles ran the Gehrman-Driscoll Insurance Corporation company where Richard Gilmore was vice president, overseeing the international division, until Floyd and the other executives started pushing him toward retirement. When Richard quit and started his own business, Jason approached him and proposed a partnership.

Richard: Why?

Jason: Because I want to do something on my own. I want to work someplace that hasn't known me since I was six. I'd like to get through an entire day without being called Digger. And I really, really want to piss off my dad.

—Season 4, Ep. 3 "The Hobbit, the Sofa and Digger Stiles"

Jason soon renewed his acquaintance with Lorelai and began pursuing her romantically. He was persistent in the face of her repeated rejection, and wore her down. They hid the relationship from Lorelai's parents for five months, until the night that Floyd informed Richard and Jason that he was suing them because of the clients that Jason took with him when he left his father's business... and revealed that he'd had hired a private investigator to tail Jason.

Jason: Which PI did you have on me? Paluso, I assume?

Floyd: He's the best. He gets everything. It's how I found out your daughter is dating my son.

Emily: That's not true!

[Everyone looks at Lorelai, who is speechless.]

—Season 4, Ep. 18 "Tick, Tick, Tick, Boom!"

Richard and Floyd made a deal behind Jason's back that allowed Richard to create a boutique company under the umbrella of Gehrmann-Driscoll. When Jason told Lorelai that he was suing her father, she broke off their relationship. Though he tried to win her back, even showing up at the Dragonfly Inn on the night of its test run, Lorelai had already moved on, to a relationship with Luke Danes. That night at the Dragonfly Inn to get him away from the Inn, Sookie and Michel call his cell and tell him his condo is on fire while pretending to be somebody else so Jason leaves to go see his home.