The Great Gilmore Boyfriend Debate

Anyone who’s watched the complete Gilmore Girls series has an opinion on this subject. It’s just a fact. Rory and her mother have a string of boyfriends over the seven seasons and debating about which was the best pairing is an ongoing issue, even though the show itself has been off-air for some time now. So in light of the impending cast reunion, I thought it was an appropriate time for me to throw in my two cents.

Lorelai had four steady love interests throughout the show: Max (Rory’s teacher from Chilton), Christopher (Rory’s father), Jason (Mr. Gilmore’s business partner) and Luke. But since Lorelai literally ran away from her wedding with Max and Jason turned out to be an absolute jerk, I’m only going to focus on the remaining two men.

Most people can fairly comfortably agree that Luke was a better pairing for Lorelai than Christopher. Christopher might have fathered Rory, and he and Lorelai might have been high school sweethearts once upon a time, but he grew up idealizing a relationship with Lorelai that just didn’t exist. He was subconsciously trying to make something work twenty years too late in a misguided attempt to fix a mistake he made at sixteen. He kept elbowing into her life, messing up relationships and making promises to the Gilmores that he couldn’t keep. And when he did finally seal the deal with Lorelai, their relationship failed because the reality couldn’t live up to the idea of what they were “supposed” to be. If there ever was one, Christopher missed his window.

Luke was there for Lorelai beginning in episode one. Their romantic relationship developed on a foundation of friendship and honesty; they respected each other. I’m not saying everything between them would always be perfect, their breakup and Lorelai’s subsequent marriage to Christopher certainly proves that they had issues as a couple, but Luke never tried to change Lorelai …he just fit himself into her world and loved her for who she was. At the end of the show they’re not technically together, but Luke organized a goodbye party for Rory. He loved Rory like his own daughter and was very clearly still in love with Lorelai at the end of the show. My suspicion is that they managed to work it out in the end.

Rory’s relationships are a bit more complicated than her mother’s. She had a bunch of love interests throughout the show, but for the most part she was a relationship girl, so I’m going to limit this discussion to the Big Three: Dean, Jess, and Logan.

As Lorelai described him, Dean was the best kind of first boyfriend. He was respectful, he was patient, he was polite, and everything that a girl could want at sixteen. In a sense, he was perfect. Which is the part that gets to me. In being her boyfriend, Dean seemed perfectly content to make a lot of his own life just revolve around Rory. Sure, he had school and a job, but basically he moved into town and got absorbed into his relationship. For someone supposedly from Chicago, he was kind of small minded that way. We never know him to have many friends other than Rory and one or two off mentioned guys, so he comes off as a very immature character overall. In short, while Dean was nice, he wasn’t good enough for Rory long term. He was always going to be there for her, the dependable and lovable guy, but he was never going to challenge her.

Jess, on the other hand, was nothing but challenge. Rory fell for his bad boy attitude the minute he handed her that scribbled in copy of Oliver Twist and we all knew it. The fact that she continued to see Dean for another half season was just part of the dramatic flair. Jess was smart, witty, and intriguing and every girl has to fall for that at least once in her life. Not for one minute did the audience doubt that he loved her, but man did that boy have issues to work out, too. For someone so intelligent, Jess was remarkably slow to get his life together. He left her days before graduation and none of us were surprised that he didn’t even call; he just bailed. However, two seasons later he reappears in one of the best displays of friendship on the show. When Rory’s life was in a shambles, when she’d dropped out of Yale and landed in a months long standoff with her mother, Jess was the one who showed up on her doorstep and was honest enough to slap some sense back into her. “This isn’t you,” he said to her. And out of all the people who’d questioned her about  her choices, his was the only voice that got through. He got his life together and then helped her back into hers. Though technically we only see Jess one more time after that, (when Rory goes to Philadelphia for his book release) I like to think that Jess and Rory remained friends.

And then there’s Logan, my admittedly least favorite of all the boyfriends. A lot of people really like him, but something about Logan always got under my skin. I never cheered Rory on as she pursued him, never liked the way she got dragged into the rich kid preppy side of Yale her grandparents were from, and hated the way he just let her stop doing things. He didn’t try and talk her out of it when she dropped out of Yale, he didn’t stand by her when his father crushed her dreams of being a journalist, and he continued to dominate their relationship with jealousy and subtle emotional manipulation the entire time that they were together. She stole a boat to impress him, fought with her mother about him, and the whole time he never got to know the Stars Hollow side of who she was. Rory fell for Logan and I can get why she did, he was smart and surprisingly thoughtful sometimes, but that relationship was never healthy and I’m glad that she said no when he proposed to her after her graduation from Yale. I don’t think she would have been herself with him and I don’t think, ultimately, that he would have been happy with her either.

In the end, I think Rory ended the show exactly where she was supposed to: twenty-two, single, and searching for a first job to start her career. For seven seasons, we saw ourselves reflected in her and her choices; it was only right that she finish the show the same way. She stood up for herself, was honest about what she wanted, and was true to her character. She wasn’t defined by a relationship.


Care to give your two cents? Let me know who you think Lorelai and Rory should have ended up with in the comments down below!


2 thoughts on “The Great Gilmore Boyfriend Debate

  1. Oh! You hit the nail on the head with all three.
    Lorelai is definitely difficult to be in a relationship with – she went a little kooky when the whole April plot line developed (hated it) and seemed pretty impulsive when it comes to love. That being said, I liked her and Luke together.
    Rory – hmm. Part of me wishes Jess would have come back in the end and at least reconnected with Rory before she left for the Obama trail. Even if nothing happened, they could have alluded to it happening! I loved when Jess called her out for dropping out of Yale. loved it.
    I could go on forever, sorry. GREAT POST!


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