And Now, Let’s Argue About the Gilmore Girls Boyfriends

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Photo-Illustration: Maya Robinson and Photos by Getty Images/CW

This post originally ran on September 24, 2014. We are re-running it in advance of the new season of Gilmore Girls.

Margaret Lyons, Lindsey Weber, Danielle Henderson, Amanda Dobbins, and Joe Coscarelli debate maybe the most important of all Gilmore Girls questions: Which boyfriend was the best?

Amanda Dobbins: Hello, friends, and thank you for joining me to argue about fictional boyfriends from a show that aired ten years ago. At some point, I’d like to talk about all the major Gilmore Girls relationships — for both Rory and Lorelei — but let’s get right to the big question: Are you a Dean, a Jess, or a Logan?

Danielle Henderson: I’m team Jess.

Margaret Lyons: Jess. Always.

Joe Coscarelli: Anyone but Logan.

Lindsey Weber: Hi, guys. I’m a Dean. I know, I know.

DH: LINDSEY.

LW: Yes, I realized that this was going to be a problem for everyone, but someone’s gotta stand up for Dean! I’ve been thinking about why I like him so much, and a lot of it has to do with my own experiences. He’s Rory’s first boyfriend, he’s tall and handsome, and he makes her a car. A CAR.

DH: She lost her virginity to him WHILE HE WAS MARRIED. Forever nope.

LW: I know he’s a total cheater, but I don’t think he would’ve cheated on Rory if he stayed with her? (This is already going downhill for me, I realize.)

ML: LW, did your first boyfriend get married when you were 19? Also, Dean is a dumbass. Like, a nice first boyfriend by any standard, but what, Rory’s supposed to stay with him? What would they talk about? After high school, they have nothing in common.

JC: Rory giving Dean reading assignments was always heartwarming, though, and a nice corrective to the usual “high-school boyfriend teaching blank-slate girl how to have taste” thing. Speaking as a reformed one, all teen boys could use a bit more Jane Austen and a bit less Hunter S. Thompson in their lives.

LW: I think I like his puppy-dog nature, too. I like how he is way stupider than her. She could totally boss him around and make him do whatever.

JC: Dean is the ultimate floppy-haired high-school dope. The kind of guy who wears short-sleeve shirts over long-sleeve shirts and doesn’t see the problem. Never forget his bad bangs and scruff when he cheated on Lindsay with Rory.

LW: HE MADE HER A CAR. A CAR! Okay, sorry. I want a shitty high-school boyfriend with a car.

AD: Okay, let’s go back to Jess, though, since you all love him so much.

ML: Doesn’t everyone’s high school/high-school experience have a Jess? I feel like he’s the perfect kind of 16-year-old character in that he seems soooOOOOOooo cool when you’re 16 (well, younger) and like such a dirtbag bad idea as an adult. That said, I feel he is the only person who truly understands Rory, and she pushes him away because of that.

AD: Except ... he is the one who ditches her? Which makes him more appealing when you are 16 (or 30), of course, but he is not exactly a reliable, supportive presence.

ML: He’s not reliable at all. But when he comes back to her dorm room and he’s like, “I wasn’t ready before, but I’m ready now!” And he’s crying? I cry.

JC: There's a great moment after Dean storms out on Rory during the dance marathon (poor Lorelai) and clears the way for the inevitable slow-motion wreck that is the Jess period in which Luke is way more worried than anyone, which I think is telling. Lorelai tries to soothe him and says, "I think Rory’s 17 and it’s probably about time for a Jess.” Luke probably was a Jess, which is why he knows it can only end in heartbreak. But Lorelai — who had her own Dean but got a baby instead of a bad-boy exit ramp! — knows that's okay.

LW: He crashed her car :(

AD: If you like cars so much, why aren’t you TEAM LOGAN?

DH: I think Jess has the emotional heft Rory needs, but he can’t get out of his own way. He’s super sad, but not because of circumstance; he’s just sad because he’ll always find a way to sabotage himself. I think his showing up at the dorm, or when he convinced Rory to go back to Yale, was totally selfless and showed his capacity for growth. Which you kind of want in a partner, you know?

ML: Also, Rory and Jess have a shared history of not-great parental role models. And that’s something that could bring out the worst in each other, oooooor it’s something they could explore very effectively in couples therapy.

AD: Is it time for me to defend Logan yet? Because I am prepared to do that.

ML: The Good Wife has made me more sympathetic to Logan. But if you pick Logan as your favorite of Rory’s boyfriends, doesn’t that make you sad? He is kind of terrible for every moment he’s kind of nice. “Rich dudes need love, too”? Barf forever.

LW: Logan is bad. It’s pretty shocking how long Rory let that go on.

JC: The ultimate rich weenie.

DH: Logan is a one-night stand at best, and the nightmare of your life at his worst.

ML: My essential take on Logan is that I get why Rory dated him, but I don’t get why she dated him for so long.

AD: Because he’s ... charming and handsome and made her life significantly easier. Note that I did not say better — though honestly, all the shit that goes wrong in Rory’s life during that time is Rory’s fault. (Fine, or Logan’s dad’s fault.) I feel like Logan gets blamed for a lot residual crap from her grandparents and his parents and Lorelei and Yale and everyone else, but the truth of the matter is: He was mostly nice to her. He tried to help her. And he was cute.

ML: We get it, Amanda, you want to date rich dudes.

JC: I will put aside my general revulsion with Logan — never trust a blond man — to agree: He treated Rory amazingly well for a college boyfriend. But he never understood her as a human, he just liked the way their stats lined up. But there’s nothing worse than a grand romantic gesture that’s ultimately empty. Like proposing in front of her entire family the night before she graduates from college. Yuck.

LW: It was really, really sad, though, when Logan’s dad told Rory she couldn’t write? Logan’s family were assholes.

ML: I loved it when Mitchum was like, “GTFO.” He’s the first person ever not to roll out the red carpet for Rory. Tough tacos, lady. You don’t get to call in a favor and then be whiny when it wasn’t the favor you wanted.

LW: Who did Rory date the longest?

DH: Was it Logan? I think it was Logan.

JC: It is healthy for relationships to get gradually longer as you age! But it was way too long.

ML: Consensus question: Are any of these guys Rory’s OTP (One True Pairing)? Like, do we want her to wind up with one of them in the future?

JC: NO! And I think the writers were ultimately pretty clear about this, much to the show’s credit. Rory’s romances were never elevated to the same level as Lorelai’s because that’s just not realistic — the girl was 15 and then she was 22, and she was always smart and raised well enough to know there were no deadlines on love. (Corny alert.) 

Does that mean she and Jess didn't have an ill-advised Before Sunset–ish weekend when she was in L.A. for work? Or that Logan didn't get bored of whatever trophy wife he eventually found and send her an emo email asking to meet up? Definitely not. But it ends there, I think.

LW: I agree that Rory, unlike Lorelai, was not (maybe purposefully?) given a OTP in Gilmore Girls.

DH: Who said that her OTP was Paris? That seems right.

JC: Or Rory was Paris’s, but it was unrequited.

AD: I want to go back to LW’s point for a second, since it raises another question: Do we all agree that Luke was Lorelei’s OTP?

DH: No way. Their whole relationship felt forced and unnatural and uncomfortable. Like, just be friends, occasionally have sex, whatever. Don’t make this guy the love of your life, don’t make this loony lady the love of your life. It was too convenient.

LW: I’m glad we can all agree that Lorelai was a nutcase. But Luke was totally her OTP! For me, that was the center of the show. No matter how badly we all wanted her to choose Max. She didn’t want him. That idiot. (Lorelai, not Max. I love you, Max.)

ML: I’m sorry, they absolutely are OTPs. I don’t think either is really capable of healthy relationships, but ... they are the ultimate TV couple in so many ways to me.

JC: Luke and Lorelai forever. Only a curmudgeon like him could put up with a headcase like her. And for as stable as he was, Luke was never boring! Which can’t be said for the rest of her guys, who all had a little too much in common with her father.

AD: Can we at least agree that revenge-marrying Christopher is an unforgivable offense? Like, do not take her back after that. Sorry.

DH: TOTALLY.

ML: We should all be so lucky as to revenge-marry someone that hot.

AD: Who wants to date rich dudes now, Marg.

ML: Christopher is fake rich, though, just for plot contrivance so Rory would have another source of unlimited funds. (P.S.: GET A JOB, RORY.)

AD: This seems like a good moment to remember that Digger existed, and that he was funny.

ML: I loved Digger. I wish he had been a more present character for longer, even just as a friend or mentor. I want Chris Eigerman to be on more shows.

LW: Can we all agree that Jackson and Sookie are actually the best couple? Or Lane and Sebastian Bach? (JK.)

ML: Lane got the shaft. She got the worst possible end to her story — I am still super bitter about Lane. Nothing wrong with her dude per se, but ... the girl deserved more adventures. Paris and Doyle are my dream couple, and basically what I aspire to be.

LW: Remember when Lane dated Adam Brody? Dave.

ML: I was very sad when Dave Rogalsky “moved to California.”

JC: Dave, not Dean, is actually the ideal high-school boyfriend. Nerdy enough to be nonthreatening, but also unfailingly sweet and bad enough to lie to your mom. The proto–Seth Cohen, if you will.

AD: Okay, final question: Do Luke and Lorelai stay together? (The second time around.)

LW: In my dreams? Yes. They have to.

DH: Stars Hollow would never let them live it down if they split up again, so I think they do. Plus, I think they’d be better as curmudgeonly old people than they are curmudgeonly (middle-age?) people.

ML: Of course they do! Remember that time Lorelai has a dream where she’s pregnant with twins and Luke is her husband? I think that comes true, even though they are probably too selfish to raise more kids. Luke is all in! Come on!

JC: Lorelai sings him “I Will Always Love You,” remember? “Always.”