Was Dean Rory’s best boyfriend—or do I just have terrible taste?

As I’ve got older, I’ve gone through a lot of strange and unnerving changes. For example: I like doing laundry now. I prefer eating summery salads to devouring ten chocolate brownies in one go. I like white wine more than Smirnoff Ice. And I think Dean was Rory’s best boyfriend.

I can just hear 17-year-old me’s jaw dropping. Because I have always been Team Jess. Always. From the moment he stepped off the bus into Stars Hollow, I was in love. He was dark, dangerous and exciting; he was the bad boy just waiting for Rory to change him; my god, was he handsome as hell. In short, Jess was the epitome of everything my drama-crazed, romance-obsessed teenage self was looking for.

I loved watching him fall for Rory. Gone was Dean’s chaste, boring fawning over her; this was sexy. Every time Jess curled that upper lip, you could see him wanting her. I loved that he was into literature. I loved that he wore leather jackets. I even loved that he left, rudely, heartbreakingly, without a word. (Oh to be a self-destructive teenage girl again. I even dated a guy solely because he reminded me of Jess—in that he was horrible to me and everyone around me.) There has never been any question in my mind: it’s always been Jess.


But then, this year, I started re-watching the show. I waited patiently through Season 1, still more interested in Chad Michael Murray’s handsome cameo than in the painfully sexless Dean. I was watching with a friend who’d never seen it before as we approached Season 2, and I counted down the episodes until Jess was about to arrive. The whirlwind, heartbreaking, beautiful Jess.

Well, where was he?! The Jess we got was dull, rude and unpleasant. He wasn’t funny; he definitely wasn’t cute. Sure, there were a few moments that still got my heart fluttering a little (like the scene where he fixes the sprinkler only to break it again, or that AMAZING first kiss scene), but overall he left me massively underwhelmed.


And yet I still have a serious soft spot for the “troubled bad boy who learns to love” trope—so why did Jess leave me so cold this time around? I think it’s because, while his chemistry with Rory was undeniable, he stilted everything else.

Dean, on the other hand, fit right into the Gilmore lifestyle. He ate their food and watched their films and laughed (even if in bemusement) at their jokes. He went along with Rory’s bits, and Lorelai’s too. In fact, many of the best scenes were made up of Rory, Dean and Lorelai hanging out in the house. And when he advises Max on how to date a Gilmore girl, it’s clear that he loves them—both of them.

I still think he’s a little vacuous, and I still hate his curtain hairstyle (and when he comes back in season 4, I hate his shaggy long hair even more), but I do think he complemented Rory the best—and not just Rory, but Lorelai too. He may not have been as sharp as Jess, or as adventurous as Logan, but he adored the Gilmore girls for the same reasons we did. He was the only one who truly understood their bond, and the only one who never tried to replace it.

And he always changed the water bottle.


So what do you think? Was Dean Rory’s best boyfriend? Or do I really just have terrible taste? Comment below or let me know your thoughts on Twitter!

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