A look at Rory Gilmore's dating history

There's an old TV adage that says, "Happy couples aren't very interesting."  Though we want stability in our real life relationships, it's generally not what we want from our television couples, give or take an Eric and Tami Taylor.  That's the reason why fictional couples don't last very long -- eventually, even those for whom you most fiercely rooted to get together run the risk of stagnating.  If that's the case, then it's natural for a show that ran as long as Gilmore Girls did to have its two main characters go through so many relationships.

In my piece on Monday where I did an overview of the show as a whole, I mentioned that Gilmore Girls tracks Rory Gilmore's entire adolescence over the course of seven seasons.  While not everybody knows what it's like to go from a prestigious high school to an Ivy League university, there is something universal about the basic coming-of-age she experiences.  It makes sense (and is somewhat amusing), then, that on her way she cycles through many of the male archetypes that one is likely to date in their young adult years.  The shipper battles are intense within the Gilmore Girls fandom, and much blood has been shed over Team Dean vs. Team Jess debates.  (Meanwhile, the few Team Logan members remain hidden in a corner.)  But really, all of the internecine squabbling is pointless, because I have this theory that we're supposed to feel the same way that Rory does about the men on the show at any given moment.  Gilmore Girls is a show from the perspective of these two women, so it's natural that our opinions -- or mine, at least -- about people change when theirs do.

I was too busy nursing my own crush on her to care much about the boyfriends, but regardless of whom you prefer, you can't deny that Rory Gilmore is very crappy at relationships.  From making it obvious that she has feelings for Jess when she's still with Dean, to later sleeping with Dean when he's married to another woman, her bad decisions with men are the one major flaw in an otherwise great person.  So without further ado, let's delve into these boys and their respective archetypes:

The All-American Jock: Dean Forester

Ah, Dean.  Square-jawed, broad-shouldered, football star Dean.  He's pretty much the natural choice for Rory to have as a first boyfriend.  Their relationship was a nice mirror to the rhythm of season one -- sweet, innocent, awkward, and still trying to find its footing -- and rewatching a few episodes made me realize how lovely their tale of mutual first love was at times.  Yet here's where my theory kicks in: He turns into a total knob around the time that they break up.  I don't think Amy Sherman-Palladino had quite realized that she wanted Rory to cycle through these archetypes of men in the early stages of the show, because he initially starts out as somebody who liked and read books, but gets retconned into a lunkhead once Jess enters the picture.   He sticks around long enough to eventually go back to being a decent guy (conveniently, when Jess leaves the picture) when he gets married to another girl in season four, and eventually plays a pivotal role in the Rory and Lorelai's first big fight, after DJ Rory Gilmore Home-Wrecker sleeps with him.  Overall, I was never crazy about Dean, even during his most pleasant moments.  He's just so bland, but apparently some people are into that!
Highlight Rory and Dean episode: "Kiss and Tell" (season one, episode seven)

The Brooding Bad Boy: Jess Mariano

Listen, I hate this archetype.  As a guy who couldn't be further from the tortured bad boy type, I've never understood why girls are into people like Jess.  And he's an especially odious bad boy.  He's just sour and unpleasant to everyone in his first handful of episodes, but we're supposed to think he's cool because he reads Jack Kerouac or whatever.  Of course, "The Theory" comes into play with him as well.  Once Rory starts liking Jess a bit more, he becomes slightly more likable.  He's still brooding and smart-mouthed, but his actions are filtered through the lens of Rory's growing infatuation.  Even the fiercest Rory-Dean shippers can't deny the greatness of "Teach Me Tonight" as an episode.  (Among the things that can't be denied is also the hotness of their first kiss as a couple.) However, "The Theory" gives and takes in equal measure, and Jess goes back to being insufferable sometime around "Keg! Max!," right in time for him to be shipped off to Venice Beach for a failed backdoor pilot.  Jess might be my least favorite of Rory's boyfriends, but it was nice to see that he grew into a mature adult when he briefly returned in season six.
Highlight Rory and Jess episode: "Teach Me Tonight" (season two, episode 19)

The Smarmy Bro: Logan Huntzberger

Honestly, I've never really been on board with all of the Logan hate.  Before I even watched the show, one of the things that always stood out about the Gilmore Girls discussions that I skimmed over was that it eventually became filled with a bunch of "ugh, Logan" complaints.  When I began to actually burn through the series, I thought I was going to hate Logan when he was first introduced too.  He was heavy on the rich guy faux charm, and the idea of him and Rory pairing up in the future didn't exactly fill me with excitement.  But he quickly settles into the show -- just as Rory starts to warm up to him, further reinforcing "The Theory"! -- and I stopped disliking him.  Now, I can't say that I ever loved him, but he was never a detriment to the show for me.  I think that the anti-Logan brigade gets some of its fuel from the fact that the Yale years of the show featured a decline in quality in most people's opinions.  While it could be that people hated the latter seasons partially because of Logan, it's also easy to see how enjoying the show less could make someone dislike Logan by extension.
Highlight Rory and Logan episode: "You Jump, I Jump, Jack" (season five, episode seven)

The Pining Friend: Marty

Technically, Marty doesn't belong on this list because he and Rory never dated, but I'm putting him here because THEY BELONG TOGETHER.  He's not blessed with Dean's good looks, Jess's cool hair, or Logan's wealth, but he's such a nice dude.  He's the underdog that you can root for.  After his meet-gross with Rory, when she finds him naked on the ground in their dorm hallway, he quickly slides into the "Male Best Friend" slot.  Then he just kind of disappears once Rory and Logan start to become a long-term couple, before returning in the final season.  In a way, the writers use him as this looming specter that symbolizes Rory's change over the course of her four years at Yale.  In season four, when she was just a sweet freshman, the two of them were friends, but in season seven they couldn't manage to get along after she'd spent so many years in Logan's sphere.  Some might find him to be a bit of a jerk in the final season when he pretends to not know Rory in front of Lucy, but after being mistreated by Rory for so long, he'd built up enough goodwill in my book.  What does it say about me that I like Marty more than any other guy on Gilmore Girls?  I prefer not to think about it too much...
Highlight Rory and Marty episode: "The Hobbit, the Sofa and Digger Stiles" (season four, episode three)


Gilmore Girls Week continues tomorrow at 8:00 AM EST with a list of the show's top 10 episodes.  The series kicked off on Monday with an overview of the entire show, followed by Tuesday's essay on season four's "The Incredible Sinking Lorelais."