Dean’s the worst!


Ranking Rory’s boyfriends in anticipation of the ‘Gilmore Girls’ revival

By Sharon Miki, Contributor

Want to raise the blood pressure of any Gilmore Girls fan in zero-to-five seconds? Tell them how much you hate one of Rory’s boyfriends. Nothing causes more derision amongst fans of the coming-of-age hit about a former teen mom raising a teen daughter than discussions of the “correctness” of certain relationships, and—with the show confirmed as returning with a limited run on Netflix after a 10-year hiatus—now there is finally an opportunity to definitively prove who our girl would be happiest with. Casting news showing the return of main Rory-boyfriend actors Matt Czuchry (Logan), Jared Padalecki (Dean), and Milo Ventimiglia (Jess) has reignited a favourite debate: who was Rory’s best boyfriend? Let us briefly explore, from worst to best, the past loves of Rory Gilmore.

  1. Dean—a.k.a. “The Absolute Worst”

There is a common misconception that Rory’s first boyfriend, small-town-hot-guy Dean, was the love of Rory’s life. If you look closely, however, Dean was indeed tall and hunky…but also slightly doltish with a penchant for nostril-flaring, verging-on-stalkerish jealous rages. For a sensitive, intelligent, striving-to-be-worldly girl like Rory, Dean was always just going to hold her back and stare blankly at her while things went over his head. Oh, yeah—he also cheated on his wife (who, honestly, he was borderline abusive towards during his whole guilty-about-cheating phase) with Rory. The worst.

  1. Marty—pouty much the worst

The quintessential angry “nice guy,” Marty was Rory’s oft-flirty friend-zoned male companion during her first few years at Yale. She was never in a place to be with this dude, but he continued to follow her around and then stomped off in a huff when she didn’t want to be his girlfriend. He further proved his terribleness by being sketchy and lying about knowing her when they met again a few years later. He also destroyed Rory’s friendship with Lucy. Rory doesn’t make friends easily (could be the over-attachment to her mommy), so this is unforgiveable.

  1. Tristan—bad at being a bad boy, but okay

Tristan was Rory’s will-they-or-won’t-they Logan-lite rich, blond classmate at Chilton. They kissed once at a party and he wouldn’t let her forget it. Tristan was exciting and challenged young Rory (and he bought her tickets to PJ Harvey, bless his heart), but his attempts at bad boy antics were lame (he got sent to military school for breaking into his friend’s house with his friends for like no reason) and he suffered a hurried exit when Chad Michael Murray was cast on One Tree Hill. Tristan had the bad boy sparks that Rory needed to counterbalance her own timid nature, but lacked the depth to be her number one.

  1. Logan—some chemistry, but not Jess

Even if we forget the ill-fated final season of Gilmore Girls—which had a different team of showrunners and writers and thus totally destroyed a number of characters, including Logan—Logan was always just a pretty good choice for Rory. He had the cash to elevate Rory socially, and, to be fair, was pretty quick with the quips; but, in the end, he never really reached Rory’s level. Perhaps it was being raised as a golden boy, or the fact that he brainwashed himself on some peyote-led trip in the Life and Death Brigade (one can assume).

  1. Jess—the best

Jess had a hard time in his teens, but even when he was dealing with his own issues, he always brought Rory out of her bubble in the best way. In a world where everyone put little Rory on a pedestal, constantly telling her how pretty and smart an special she was, Jess instead asked her what she thought and showed her something new (though he clearly thought she was pretty and smart, natch). Jess and Rory had palatable, undeniable chemistry, but they also had a deep natural rapport—a connection that she only had with her mother, otherwise—that would take them into their elder years, smiling wryly. While Jess left the show in similar Tristan fashion (he was cast in a never-aired Jess spinoff), I can only hope that the new seasons of Gilmore Girls will bring Rory to her rightful lifelong partner—and he’s Jess.