11 things nobody wants to admit about Gilmore Girls

Gilmore Girls - Netflix
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Gilmore Girls

7. Digger was Lorelai’s worst boyfriend

Maybe this one’s pretty obvious and something fans are willing to admit. Jason Stiles, otherwise known by his childhood nickname Digger, was Lorelai’s worst boyfriend. Digger arrives in season 4 as Lorelai remains in her post-Max, pre-Luke era, and he’s complicated in ways that Max and Luke (and even Christoper) never were.

So the backstory goes: Lorelai and Digger knew each other from camp, which tells us that he’s firmly a product of the world Lorelai grew up in. It’s the world she walked away from at 16 years old and never looked back, the world she still struggles to dip a toe into to have a relationship with her parents. As previously stated, it’s complicated.

To make things even more complicated, Digger worked with Richard, and before that caused an absolute clash of the titans between both families, they kept their relationship under wraps. Seemingly, Lorelai didn’t want to give Emily the satisfaction of dating someone from their world, someone who doesn’t wear a flannel and backward baseball cap to work. (That’s a complex tightrope of validation for Lorelai to walk in and of itself.)

Digger’s connections to the Gilmore world aren’t what made him Lorelai’s worst boyfriend, though. He was just… boring? They have plenty of chemistry, and they had plenty of memorable moments, like their grocery store date. (CLASSIC!) You could just tell he wasn’t endgame, that he was a stopgap romance on the way to Luke.

There’s nothing inherently wrong with a layover relationship on a TV series; they can often be entertaining and make for solid episodes, especially on a sitcom. But no one was going out of their way to actively root for Lorelai and Digger long term. They never would have worked out anyway. So, even though he wasn’t bad per se, Digger was Lorelai’s worst boyfriend on the show.