Rory had three different boyfriends over the course of Gilmore Girls, and which one was the best for her often divides the fandom. I’m very proud to be Team Jess and I am going to use the trusted Fuck Marry Kill structure to analyse Rory’s relationships with Dean, Jess and Logan…
Spoilers ahead for Gilmore Girls and Gilmore Girls: A Year in the Life
It’s quite abrupt, I know, but after careful consideration, I’ve decided that I have no choice but to kill Dean. Originally, I was going to fuck Dean because he seemed like the perfect boyfriend for Rory, especially to lose her virginity to, but he was far from it. I cannot bear the person Dean was, nor the person he turned into. Dean had his sweets moments, such as when he built Rory a car, but there are many things — both big and small — that stand out as red flags.
It’s understandable if Dean felt like Rory wasn’t making enough time for him, but he was always making her feel guilty for focusing on schoolwork, even though he knew this was really important to her because of her dreams of going to Harvard. He also made her feel bad for wanting to go to the school dance, acting like he was above it, and other events. You were never actually that cool, Dean, sorry!
Dean’s worst qualities were that he was jealous and controlling. He constantly fought (physically) with Tristan and Jess, who both had feelings for Rory, even going to the extent of sitting in on Rory and Tristan’s rehearsal for Romeo and Juliet for their English class. Dean didn’t even go to their school! He also struggled to let Rory spend time by herself or with other people. In one particular episode, Rory made plans to spend a rare evening alone doing laundry and ordering Indian food, but Paris eventually crashes her plans because she desperately wants help studying for their upcoming Chemistry quiz. Then Jess shows up with a care package from Luke’s. Dean also ignores Rory’s request to spend time by herself and shows up to surprise her, only to find himself angry and upset with Rory when he sees Paris and Jess there — but especially Jess. Luckily, Paris covers for Rory when she sees how Dean reacts. Obviously Dean was right to worry about Jess and Rory, but he didn’t trust Rory and wanted to control her every move. She was driven into Jess’s arms if you ask me!
In the episode where Dean builds Rory the car, he also says “I love you” for the first time. When Rory doesn’t respond right away, he heckles her for a response, and when she can’t say it back, he breaks up with her! Rory even begs him not to be angry with her, even though she’s done nothing wrong, which seems to be a common theme in their relationship. Although he’s a teenager, it’s highly immature for Dean to not allow Rory time to process her own feelings. He seems to get angry when things don’t go his way. When they get back together, Dean is clingier than ever, once going to the effort of leaving 4 messages with Lorelai and 10 voicemails during one evening. Yikes!
Dean eventually gets married to Lindsay, despite being far too young and still having feelings for Rory, and he winds up cheating on her with Rory (which also made Rory kinda suck, too). Not only this, but he emotionally abuses Lindsay out of guilt. After being with Rory, Dean comes home and barely speaks to Lindsay until she tells him his phone rang while he was out. He screams at her for answering it, creating some bullshit story about what if it was work and he missed picking up more shifts because they thought they called the wrong number. He tells Lindsay that he works for her and she quietly apologises like a textbook abuse victim. It’s heartbreaking to watch because Lindsay obviously doesn’t deserve to be treated like this. The series never even paints her as a bad girlfriend, but the entire opposite — she was always trying to please Dean, even going to the extent of learning how to cook his favourite food, even though she sucked at cooking!
While Jess and Logan aren’t perfect either, they evolved as they get older, whereas Dean devolved into the worst person ever. Sorry, Dean, but you’ve simply got to go.
I thought about killing Logan, I really did, but unfortunately I’m partial to a fuckboy, and Logan is the perfect person to fulfil this role. Logan may seem like the worst, but he actually has many good and bad qualities, despite coming across as nothing more than a privileged jerk most of the time — especially the first few times we meet him.
What makes Logan a good fuck? With Logan, you know what you’re getting right from the start. He’s a charming dickhead who always promises a good time. He often pushed Rory to step outside of her comfort zone and have new experiences, most of which she genuinely enjoyed — for example, when Logan reveals he’s part of Yale’s secret society (The Life and Death Brigade) and they go to an event where they jump off a big scaffolding with umbrellas, which Rory finds exhilarating. Even if Logan hurt me, which he definitely would, I’d have better stories to tell beyond the standard heartbreak than I would with the boring and controlling Dean.
Logan can still be incredibly immature. He was really rude to Jess when they went out for lunch after Jess announced that he had written a book. He also slept with his sister’s friends while he and Rory were “on a break,” which was a weird and excessive move. He even blamed them for being “worthless idiots” and said they just like to cause trouble. Dude, either own up to your mistakes or fuck off. Nobody likes a Ross!
One of the worst things about Logan, which isn’t actually his fault, is having to deal with his wealthy and judgemental family. While Rory is also from an affluent and highly regarded family, this didn’t prevent her from being subject to criticism. Mitchum crushed her dreams and other family members didn’t like how aspirational Rory was, preferring that Logan marry someone who can play housewife and host parties (much like her grandmother, Emily. Most of Logan’s troubled personality comes from growing up in this environment, where he must follow strict expectations set by his parents, whose love for him is conditional.
Unfortunately, Logan isn’t marriage material because he’s missing a few key qualities — such as providing appropriate emotional support (something his parents clearly never gave to him). He did try, but he’s mostly about grand gestures, such as buying Rory a Birkin bag and that one time he hired a barista with a coffee cart to follow Rory around campus all day. Logan is definitely capable of being more intimate and attentive, because there are times when he really came through for Rory, but ultimately he’s too distracted trying to escape his own problems. He has the capacity for improvement, and does have some positive character development in this regard, but it seems to go out of the window during the revival series.
In the revival, Logan does a Dean and cheats on his fiancée with Rory. (Season 1 Rory would hate herself if she found out she becomes “the other woman” twice in her future. I think it’d cause her to have a nervous breakdown for an extended period of time.) Logan is stuck in a job he hates because of the pressure to please his father, and an unhappy marriage because, like Dean, he cannot shake the feelings he has for Rory. The impact Rory had on these boys is just too much. Logan is still caught up in his fancy lifestyle and working, never bothering to stop for long enough to ask himself what he really wants out of life. Perhaps he’d be more appealing long-term if he had the courage to follow his heart and find a dream that’s worth upsetting his father over. He’s a smart guy and he should go after what he wants — fear of consequences never stopped him much before.
Just like Logan, Jess also had problems with his family due to lack of parental support. His troubled but kind mother and absent father made him feel alone and misunderstood in the world, which caused him to be argumentative with everyone around him, including Luke, his uncle, and Rory. I can’t say I’d be thrilled to be with a guy who was acting like a jackass, getting into fights, wasting his potential, and thinking everyone was out to get him — but the reason Jess is marriage material is because of how much he turned his life around.
There’s no question that Jess treated Rory terribly at times, with the worst thing he did being telling her he loved her and then leaving Stars Hollows without telling anyone — including Rory. It was such a shitty thing to do and it was heartbreaking watching Rory unfold in the aftermath of Jess’s teen angst. He was very bad at communication and always bailed when things got difficult. He even almost pressured Rory to have sex with him once. Gross! Jess also often tried to cause conflict between Rory and Dean when they were together, but who can blame him? Dean was like a ticking time bomb, so he was easy to annoy. Jess was also the black sheep in Stars Hollow, with everyone — including Lorelai — not liking him. This only reinforced his view that no one understood him and so he continued to act out, though surely it wouldn’t have killed him to respect the adults who were trying to help him.
Jess was smart, but he never really engaged with school so no one ever saw his true potential. When he got older, he wrote a book which was the biggest indicator that he had changed for the better — he finally committed and followed through with something he was passionate about, instead of remaining passive. When he met up with Rory and Logan, Logan kept making jabs at Jess regarding his book. While Jess made some back, he quickly removed himself from the situation by leaving and didn’t get into a fight with Logan. It’s a tremendous sign of growth that Jess knew it just wasn’t worth it. Dean, on the other hand, probably would’ve gone for Logan outside in the car park.
This was also when Jess called Rory out on her bullshit by telling her that she wasn’t being herself — she dropped out of Yale and was acting very bourgeoisie, just like the very type of people they used to make fun of. This was actually the wake up call Rory needed in order to encourage her to stop acting out and get back on the right path. It helped her to hear it from Jess because she knows that he really knows her and understands what she’s going through — but he also cared enough to still have her best interest at heart, even after all this time, and even though she’s with someone else. Jess always seemed disinterested in most things (apart from reading) while growing up, including Rory at times, though he could never fully hide his true feelings for her. He’s always been paying attention. In addition to this, Jess was the one who encouraged Rory to write “Gilmore Girls” in the revival.
Jess and Rory’s connection was always special and that’s down to their ever-present chemistry. They really did bring out the best in each other when they made jokes, challenged each other, bonded over books and debated important social topics. They both met their match from the opposite side of the tracks. Jess’s interests and his growth would make being married to him quite rewarding and you’d never run out of things to talk about. I also imagine that Jess retained some of his bad boy vibes, but not enough to make him deeply problematic anymore. It looks like Jess actually found a way to heal from his past and act more compassionately, not only to those around him, but to himself, which allowed him to finally take control and create a more meaningful life for himself.
Jess, you’re a real one. Please marry me.
Let me know who’d you FMK in the comments!