This week, I found out that Alexis Bledel, a.k.a. Rory Gilmore, is dating Vincent Kartheiser, a.k.a. Pete Campbell from Mad Men… IN REAL LIFE! Being the rabid Gilmore Girls fan that I am, I’m always excited to hear even the smallest piece of news about Alexis Bledel, but this is way more than a juicy tidbit. It’s a full on glass of fresh-squeezed Alexis juice! But of course, to me there is very little distinction between the actress, Alexis Bledel, and the character, Rory Gilmore, so it’s only natural that I think back on the men Rory has already dated and dismissed. There’s been much debate among my friends (and enemies) as to which guy was best for Rory, so I thought I’d provide a little breakdown for anyone who needs a refresher.
Played by Jared Padalecki, Dean was Rory’s first official boyfriend. She met him on her last day attending Stars Hollow High and proceeded to date him on and off for several years, including a lascivious affair while he was married to another Stars Hollow classmate, Lindsay.
Important fact: Rory lost her virginity to Dean (ahem, while he was still married).
Pros: Dean is the ultimate good boyfriend. He worships the ground Rory walks on, makes nice with her family, demonstrates incredible patience (and, hey, Rory can be pretty annoying with all the book browsing and grade-related panic attacks), and is easy on the eyes. Despite the fact that he cheated on Lindsay, I firmly believe he would have stayed loyal to Rory for the entirety of their relationship, should she have chosen to be with him.
Cons: I hate Dean. I think he is way too dumb for Rory. I know a lot of people, including some of my closest friends, will disagree with me, but I actually think it is the fault of the writers. When we first meet Dean, he’s the new boy in town. He hails from Chicago, picks up on obscure movie references, and banters easily with Rory. But by season 2, he’s transformed into a bumbling farm boy fool (and NOT in the hot way) who can’t provide even the slightest intelligent opinion on Rory’s writing, doesn’t want to see the same movies, and thinks it’s a good idea to get married right out of high school. Also, he cheats, and he treats Lindsay terribly (remember when she accidentally answers his cell phone and he reams her out?). Finally, I think there is palpable sexual tension between Dean and Lorelai, especially in the era when he is constructing the inn. And that just freaks me out.
The demise of Rory’s relationship with Dean, Jess is Luke’s nephew, who appears on the scene and promptly steals Rory’s attention and eventually her heart. Jess is the consummate bad boy – he’s everything Dean wasn’t. Whip-smart, rebellious, well-read, exciting… he definitely doesn’t treat Rory well but he’s her match intellectually. Their relationship spins out when he leaves town without even saying goodbye.
Important fact: Jess is the catalyst for Rory’s return to Yale in season 6, long after their romantic relationship has ended. It’s his criticism of her life at her grandparents’ that forces her to reevaluate.
Pros: Jess is incredibly smart and keeps up with Rory in a way Dean never could. He loves to read and talk about books, he’s a writer, he understands all of her references (although I think it’s highly unrealistic that it takes him even a second to realize who “Dodger” is when she refers to him that way), and he and Rory have a deep emotional and physical attraction. He keeps her on her toes and he is quite attractive. Bonus: the actor, Milo Ventimiglia, and Alexis Bledel dated in real life.
Cons: Jess sucks. He’s a total dick to Rory, never calling when he says he will, leaving her hanging, and excluding her from the important details in his life. He’s rude to her grandmother and dishonest about most of his problems. When Rory finally gets over him, he comes crawling back to muck up her life, trying to get her back. Jess is bad news, and no matter how cute or smart he is, he would never have made a good long-term boyfriend for Rory.
Rory’s longest steady boyfriend on the show, she dates Logan for most of college and post-college. He’s from an even wealthier background than she is, making him the first of her boyfriends to meet the approval of her rich and snobby grandparents. Logan is an interesting mix of Dean and Jess in that he is as smart as Rory (and she claims he is even smarter), quick with the witty banter, a pretty good boyfriend (eventually), but with a definite edge. For awhile, Logan gives her almost as much trouble as Jess did, first not wanting to be exclusive and later “cheating” on her when they were on a break. He’s probably the most nuanced of the three love interests, but we also have more time to get to know him and his family than we do with the other two.
Important fact: Logan proposes to Rory in the final season of the series and she turns him down.
Pros: Logan is ostensibly the best “match” for Rory. They come from similar enough families (although Shira Huntzberger would claim there’s a huge class gap between them), both attend Yale, seem to want the same kind of lifestyle (Rory-The-Later-Years is quite a little society woman), and never run out of things to talk about. Rory is deeply attracted to him and excited by him, and this never wanes throughout their relationship. Above all, he’s a reformed troublemaker with intense ambition and deep admiration for Rory.
Cons: In many ways, Logan is a rich asshole who never really grew up. He’s condescending to Marty when we first meet him (and yes, he defends himself intelligently, but still), hangs out with other spoiled dilettantes, resists commitment to Rory, buys her a friggin’ Birkin bag (I’m sure some of you will put that in the pro column but COME ON! Does he know her at all?!), and just generally annoys me. Years into dating Rory, he refers to Luke as “Duke”. Luke, the man who is a surrogate father to Rory. Does Logan seriously not know his name by then?! He’s smarmy, cocky, and loses millions of his father’s dollars in a business deal gone wrong. Also, he refuses to keep seeing Rory if she won’t marry him at age twenty-two. Lame.
Over the years, other men appeared who might have been good for Rory. Marty, perhaps, or that T.A. subbing in for her grandfather after his heart attack. But Rory doesn’t really date – and as we see when she goes out with a boy from class, she is incredibly awkward and stilted when she tries. Frankly, I’m not satisfied with any of the options we’re given for Rory’s potential lifelong love interest. I’m in the middle of my 16th viewing of the entire series, and while Logan has grown on me and I can see where he might make a good husband, I still agree with Rory’s decision to turn him down. Who knows, maybe if the show had continued she would have had a career-and-life-and-world-politics-altering affair with Barack Obama, her boss at the end of the series. Until they finally make the Gilmore Girls reunion movie, a girl can only dream.