Of Rory’s three major love interests in Gilmore Girls, it seemed like Logan would be the one to stick because the best Rory and Logan episodes demonstrate their relationship growth. They met as adults, he treated her reasonably well, despite the usual college-age misunderstandings, and he fit into her grandparents’ world in a way that neither Dean nor Jess ever could have. He was handsome, rich, intelligent, and capable – boat-stealing aside, they actually seemed like a solid couple for multiple seasons.
Of course, in the end, Rory ends up breaking things off – although not for good, as A Year In The Life proved that these two were still involved (albeit as an affair). But for fans who thought that Rory should have accepted Logan’s proposal, these are some of the biggest and best episodes of their relationship over the years.
“Written In The Stars”
Season 5, Episode 3
The episode is also Logan’s first appearance in the series.
“Written In The Stars” might not be the absolute best Rory and Logan episode, but it is an important one. That’s because it marks their very first meeting. The episode is also Logan’s first appearance in the series.
When the two cross paths at Yale for the first time, there’s undeniable chemistry between them even if Logan is doing his best to annoy her instead of outright flirt with her. Anyone watching the two interact for the first time can tell that Logan isn’t just going to be a recurring annoyance, but a regular fixture in Rory’s life.
It’s also made clear from his first appearance that he’s very different from Rory’s first love Dean. In broad strokes, Logan has more in common with Jess, Rory’s second boyfriend considering his ability to get under Rory’s skin so quickly, but it’s not until later in the season that the audience gets to know him better.
“You Jump, I Jump, Jack”
Season 5, Episode 7
Rory and Logan may have met, briefly, before this episode, but ‘You Jump, I Jump Jack’ is the episode where the two really start to get to know each other. And despite being a late addition to Gilmore Girls, fans quickly grow attached to Logan.
Rory is with Logan and the Life and Death Brigade for an article, and while she still sees Logan and his friends as unintelligent rich kids throwing their money around, she also starts to get a little bit interested in this life. It’s a glimpse at what hers could have been – or may still become. When Logan pushes her to jump off the tower with the rest of the group, it’s a moment of exhilaration for the rule-following Rory, and it’s easy to see this as the start of their relationship.
“The Party’s Over”
Season 5, Episode 8
This is a heartbreaking episode for fans of Rory and Dean, but a fantastic one for everyone else. In it, Rory and Dean are attempting to create a relationship again, and it just isn’t working. This is driven home to them both when Dean comes to pick her up from a party at her grandmother’s house, and finds her tipsy, in a gown and jewels, surrounded by rich young men in tuxes. It’s the last straw, and ends Rory and Dean for good, leaving her to turn to Logan for sympathy.
The latter is the part of the episode that will appeal to Logan fans. This episode makes it clear that Rory’s life has changed; she isn’t the same teenager who fell for Dean the moment she met him. This is also the episode that makes it clear that Rory and Logan have a connection since she actively seeks him out to sympathize with her.
“But Not As Cute As Pushkin”
Season 5, Episode 10
This episode sees Rory giving as good as she gets, when Logan and his friends prank her. They burst into one of her classrooms, with Logan declaring undying love, his friend coming in to ‘fight’ Logan for her hand, and then Finn showing up in a full Bobby uniform to ‘arrest’ them both. Rory is humiliated rather than amused, but enlists her grandfather to talk to Logan… and congratulate him on their engagement!
It’s a phenomenal moment for Rory and Richard, of course, but it’s also great for Rory and Logan. Not only is Logan clearly putting in an incredible amount of time and effort to get her attention, but Rory proves that she can beat him at his own pranking game. It’s one of the lighter episodes for their relationship and one that is truly fun for fans.
“Wedding Bell Blues”
Season 5, Episode 13
After the entire first half of season 5 building up to it, Rory and Logan finally get together (physically, at least) in this episode. Unfortunately, they give in to their attraction at the party for Richard and Emily’s renewal of their marriage vows.
Of course, it all goes horribly wrong as they are caught in the act, rumpled and embarrassed, there’s a lot of extra drama, yelling, and general chaos… and Logan tells Rory that he doesn’t want a serious relationship, which comes as something of a blow to her at first. But all that aside, it’s amazing to see them finally admit how they feel about each other, at least on a basic level.
For fans who love the more dramatic and soap aspects of Gilmore Girls, this episode is certainly a crowd-pleaser. It also kicks off Lorelai’s disapproval of Logan, though she does try to be civil to him for Rory’s sake in the future.
“Say Something”
Season 5, Episode 14
Rory isn’t entirely sure how to pursue Logan.
In season 5 of Gilmore Girls, Rory and Logan’s relationship is brand new. Since they start off as two people with chemistry who simply hook up now and then, Rory isn’t entirely sure how to pursue Logan. She is used to being the person who is pursued, since both Dean and Jess made their feelings for her very clear in high school. This episode sees Rory trying to figure out how to get Logan to be more interested in spending time with her, which is why it’s so fun.
Rory is invited over to Logan’s, but when she gets there, he and his friends are busy playing poker, which means she doesn’t get the time alone with him she wants. Despite his friends not being particularly likable, Rory still sticks out the entire game night with them and falls asleep on the couch. It’s an episode that shows how committed she is to getting to know Logan and figuring out where they’re going, even if they’re still “just having fun” at this point in the series.
“Jews And Chinese Food”
Season 5, Episode 15
This is the episode in which Rory and Logan become more than just flirtatious friends. Rory starts spending time with her friend Marty again, primarily watching movies and eating junk food, but when Marty tells her that he has feelings for her, she has to admit that she has feelings for Logan. For Rory, hooking up with Logan has become more serious.
Logan interrupts one of their hangouts, which is what prompts the admission from both of them. Eventually, Logan admits that he wants more from Rory as well, and he does it by climbing through her window to pay her a visit. In other circumstances that might have been creepy, but Rory had been waiting for Logan to admit the same, setting these two on their path to a relationship that would last throughout the rest of the series.
“Pulp Friction”
Season 5, Episode 17
Despite how well they work together later on, the start of Rory and Logan’s relationship is incredibly rocky, as they try (and fail) to ‘keep it casual’. Despite how strong their feelings are for one another, they repeatedly try to make their relationship one that isn’t particularly serious. That includes not being in an exclusive relationship. Of course, this all goes horribly wrong when they end up at a Tarantino-themed party with different dates.
Unsurprisingly, jealousy comes up, and Logan starts to realize that actually, he might not want to be so casual after all. Rory already knows that she doesn’t want to be casual, but she’s been trying to maintain a casual relationship, believing it’s what Loga wants. It’s a complicated episode, as the audience wants to root for Rory and Logan, but also can’t help feeling bad about how they ignore their respective dates… but in the end, this is a big one for the pair.
“But I’m A Gilmore”
Season 5, Episode 19
Most of the time, Rory doesn’t really seem like someone raised with money – because she wasn’t. Lorelai spent most of Rory’s life keeping her away from the wealthy lifestyle of Richard and Emily. It’s only recently that she has become a part of Richard and Emily Gilmore’s uber-rich world because of the agreement that her grandparents would pay for her schooling.
This episode does show, however, that she still knew, in the back of her mind, that she came from money… because she is shocked when it seems like Logan’s family thinks she doesn’t come from enough! What makes this episode special is that it shows the two of them in a real relationship – and Logan taking her home, and defending her, shows just how important Rory has become to him.
“A House is Not A Home”
Season 5, Episode 22
The end of season 5 starts a rift between Lorelai and Rory that isn’t particularly fun for the audience. Lorelai doesn’t like that Rory goes to Richard and Emily for help, and Rory doesn’t like that Lorelai can’t understand why she needs help. They can’t see eye-to-eye and it leads to Lorelai holding a grudge and Rory floundering for a bit. Before that happens though, Rory has to get arrested for stealing a boat, which is where this episode picks up.
Logan also takes a very adult step forward in the relationship with Rory…
Rory, Logan, and a few friends are arrested. Lorelai is not thrilled, but she tries her best to understand where Rory is coming from and how she ended up in trouble. The reason this is such a good episode for Rory and Logan though is because Logan genuinely tries to help Rory with the consequences of her actions. Logan calls the Gilmore house to tell Rory and Lorelai that his father’s lawyer is going to take care of everything, but Lorelai is too proud to accept that and dismisses him. Logan tries to do the right thing and use his money and connections to help Rory, but Lorelai will have none of it.
Logan also takes a very adult step forward in the relationship with Rory when he realizes that Rory is acting out because she’s so angry and hurt by his father telling her she won’t make it as a journalist. Logan encourages her to ignore his father. He also reminds her that for a relationship to work, they need to talk about things, like when his father upsets her. It’s a refreshingly mature approach from Logan who has been relatively immature up to this point.
“Welcome To The Dollhouse”
Season 6, Episode 6
“Welcome To The Dollhouse” is an episode that parallels a much earlier episode of the series for Rory and her relationship. Early in the series, Dean told Rory he loved her, and she wasn’t ready to say it back just yet. Here, she’s the one to tell Logan she loves him just as Richard begins pressing Logan for more information about the future of Logan’s relationship with his granddaughter. Logan, like Rory before him, isn’t ready to say the L word just yet.
It’s a conflict for them that allows the two to have real discussions about their relationship as the show moves forward and moves away from the pranking and shenanigans of their early courtship, allowing Rory to slowly shift into having a real adult relationship despite the obstacles still to come.
“Just Like Gwen And Gavin”
Season 6, Episode 12
Logan and Rory’s relationship comes apart and back together again a few times in the show. After Logan loses Rory, this is the episode in which he pulls out all the stops to get her back.
He does the typical things a wealthy fictional character can do like sending lavish gifts and flowers and repeatedly trying to get in contact with Rory, but the two things that endear him to fans in this Rory and Logan episode are commissioning a coffee cart to follow her around all day and going to Lorelai for help.
Logan admits to Lorelai of all people what a grave mistake he’s made, and Lorelai ends up writing a letter to her daughter (whose contents aren’t revealed in the episode but has been on display for fan conventions before) on Logan’s behalf. It’s a surprising decision on Lorelai’s part since she’s not particularly fond of Logan.
“Friday Night’s Alright For Fighting”
Season 6, Episode 13
By this point, Rory and Logan have had their ups and downs, but this is a big one, as the couple are getting back together with a big date… or they would be, but Paris has terrorized the university newspaper staff enough that the entirety of the Yale Daily News staff has walked out.
Rory, determined to fix things, ends up staying at the paper to try and get everyone back on board, and get the issue out on time – and Logan comes in to help. This is actually a big deal, as Logan is seen doing something entirely to help Rory. This is him putting his own plans aside to actually be useful to her in what she wants, and that’s something that Logan does well – and is amazing to see here.
“You’ve Been Gilmored”
Season 6, Episode 14
Logan and Rory are firmly back together at this point in the series, and when Paris kicks Rory out of the apartment for ousting her from the paper, they decide it’s time to move in together in this Rory and Logan episode. Really, Logan offers up moving in as a solution to Rory being kicked out since she already uses half of his dresser. He also gets his friends to move all of Rory’s belongings for her. Logan is incredibly thoughtful and motivated on short notice.
This may seem incredibly fast, but it actually makes a lot of sense – and starts a new page for Rory and Logan, where they feel like a couple that could be in it for the long term. Rory introduces Logan to her father here, too, just continuing to cement the seriousness of their relationship.
Lorelai doesn’t offer a lot of push-back on Rory moving in with Logan, which surprises Rory, but it shouldn’t. Though Lorelai doesn’t like Logan, she does want Rory to be happy.
“A Vineyard Valentine”
Season 6, Episode 15
For Rory and Logan fans, this might be one of the best episodes of the series, although many find it weak overall as a Gilmore Girls general episode. In this hour, they head to Martha’s Vineyard with Lorelai and Luke, and fans get to see just how good Rory and Logan can be together – and how charming and considerate Logan can be to Luke. He shares his Valentine gifts so that Luke has something for Lorelai, he and Rory are sweet and charmingly domestic, and everything is wonderful… until Logan’s father shows up, of course.
For a lot of the show, Logan’s father is the real obstacle in their relationship. Every time it seems like they make strides to have a more mature relationship, he ruins things for them. Sometimes, that’s because he gets Logan to act out, and other times, he gets Rory to. Mitch, not Logan, is the toxic part of their relationship.
“Super Cool Party People”
Season 6, Ep 20
This time around, it’s Rory who shows how much she cares for Logan in this episode, despite his tendency to take ridiculous risks. At this point, the two have been together for a while, but Logan is struggling with his father’s expectations, and he gets seriously injured in a Life and Death Brigade stunt that Rory argued with him about doing.
Despite the argument, she rushes to his side when he’s in the hospital – and far more importantly, calls his father and lays into him about not being there. Rory has previously had a difficult relationship with Mitchum, and was definitely intimidated by him – but here, she proves that her care for Logan is more than enough to overcome that.
It’s another episode that demonstrates if Rory and Logan could simply leave his father behind, there wouldn’t have been nearly as much conflict in their relationship.
“Partings”
Season 6, Episode 22
Logan shows his vulnerable side again in this episode, when Rory throws him a British-themed going away party before he heads to London for his new job. It’s a great episode just to see Rory really putting her own disappointment aside to support her partner, and to try and make sure that he feels positive (or at the very least, not upset) about leaving.
But more than that, it’s a great Rory and Logan episode for their final moments together, as Rory says she wants to go to the airport with him, and he tells her that if she did, he wouldn’t be able to go. The situation as a whole shows how they are able to support each other and understand what the other needs. Even though they don’t want to go their separate ways, they do because they value one another’s careers as well.
“The Great Stink”
Season 7, Episode 5
At this point in Gilmore Girls, Logan has already moved away for work but comes back to town to acquire a new company. When he does, he takes Rory out, and she gets the chance to mingle with his new coworkers – only to find that she doesn’t really fit into that world. It’s an eye-opening experience for Rory.
Rory also gets jealous of one of his attractive female coworkers getting to spend so much time with him. It seems like an episode that could lead to a big roadblock for them, but instead, the two only reaffirm that they’re in love with one another by the end of the hour, making it seem like Rory and Logan really are the endgame couple for her. They’ve both finally learned to be mature about their feelings and what they expect out of a relationship.
“Introducing Lorelai Planetarium”
Season 7, Episode 8
Some fans of Rory and Logan might hate this episode simply because there is quite a bit of arguing between the two – and Rory ultimately decides to move out of Logan’s apartment – but it’s a great episode to show how much they’ve grown in their relationship.
After Rory pens a scathing article about the wealthy, Logan voices how upset he is. He isn’t necessarily upset about the content of the article, but that Rory is the one who wrote it. He points out, repeatedly, that Rory is one of the very people she apparently reviles. She is a young woman from generational wealth who attended a prep school and goes to Yale. Rory doesn’t realize just how mean and hypocritical she’s being until it’s pointed out to her by Logan and two other friends.
The important part, however, is that Logan and Rory are able to talk about it. They are honest with one another and make some mature decisions about where their relationship is going (or where it isn’t) right now.
“I’d Rather Be In Philadelphia”
Season 7, Episode 13
It’s easy to think of Logan as someone who is spoiled, rich, and arrogant – but it’s episodes like this one that show just how kind and considerate he can really be, despite how the show initially paints him. Logan is always willing to go the extra mile for someone he cares about, even though he seems like he never takes anything seriously when it comes to his own life.
When Richard has a heart attack, Logan drops everything to be with Rory, and to help her, Emily, and Lorelai deal with the emergency. This is the kind of episode that Logan fans love because it proves there is so much more to him than anyone first thought. He doesn’t shy away from the scary moments for Rory, but is willing to go through them with her.
