Gilmore Girls: 10 Most Painful Breakups, Ranked - Screen Rant

When it comes to a show about a single mother and her teenage daughter, you can bet that there will be a lot of relationships and breakups, and that's exactly how it was in the popular comedy-drama Gilmore Girls. The show often had audiences choosing sides, such as Team Jess or Team Dean, to indicate which characters they believed truly belonged together.

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Regardless of which team fans may find themselves on, everyone can agree that the breakups on Gilmore Girls weren't always pleasant. Some of them hurt so much that it felt as if viewers were going through a break-up themselves.

Updated on March 17, 2021 by Kristen Palamara: Gilmore Girls mostly focused on the Gilmore family and their interpersonal interactions within the family, especially Lorelai and Rory's relationship, as well Lorelai's tumultuousness with her parents. While there was a lot of family love and drama in the series, there was also a focus on romantic relationships throughout the series. Even though there were a lot of happily ever afters when Gilmore Girls ended, they didn't come without a ton of heartbreak along the way.

Paris And Asher

Paris has a short relationship with Professor Asher Fleming while she and Rory are attending Yale. While it's an ill-fated romance from the beginning as Asher is apparently known for having flings with students, it seems like they actually care for each other despite the age difference.

Asher has a health scare and decides that he should stop dating younger women, which is for the best as the relationships he had were inappropriate. But it's still the first serious romantic relationship Paris seems to enjoy on the show so it's difficult for fans to see her upset when they end things.

Luke And Nicole

Nicole is one of the first real relationships that Luke has in the series and it seems to be a serious one as the two get along quite well after Luke asks her out when she's working as Taylor's lawyer. The two have a passionate but hectic relationship.

They try to move in together, get married on a whim, and have to figure out how to amicably split up after they realize that their marriage was a mistake.

Rory And Paul

Paul only appears in the Netflix revival Gilmore Girls: A Year in the Life and is Rory's current boyfriend. He is the punchline throughout the four episodes as Rory continually forgets that he actually exists. It's meant to be a comedic part of the plot, but it comes off as a little mean and sad.

Rory finally remembers to break up with Paul as she's obviously not happy in the relationship and Paul was pretty clueless about her feelings.

Lorelai And Alex

Lorelai and Alex briefly date and seem to be a pretty decent pair in a happy relationship. Alex tries to push Lorelai out of her comfort zone and she seems to be excited about trying new hobbies like fishing.

The two don't last and the odd part of their relationship ended is that there isn't actually a break-up scene. While the audience i spared the pain of an emotional split, they are certainly left wondering.

Paris And Doyle

Paris and Doyle start dating at Yale after she and Asher split and the two are perfectly matched. They begin their romance with no strings but quickly fall into a serious relationship when they realize they make a great team.

They have a momentary break-up in the main series that doesn't last long, but it still hurts to see Paris in pain as she struggles to put her career first while also trying to commit to their relationship. They married and are split up during the Netflix revival.

Lane And Dave

When it comes to cute couples, Lane and Dave are definitely up there in the rankings. They first meet when Lane puts up a flyer looking for a band, and soon she joins Dave's group. From there, they develop feelings for each other, even though Lane's mom is very strict about boys and dating.

Dave is willing to jump through hoops to be able to date Lane, and that's why fans were so sad to see them drift apart when Dave moved to California to go to college.

Paris And Jamie

Paris first met Jamie, an older Princeton boy, when they went to Washington DC for a student government program. Jamie asks Paris out on a date, and she is clueless but extremely nervous! They form a relationship not too long after that and they eventually sleep together — which Paris tells the entire school during an emotional breakdown.

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Paris then begins seeing a professor named Asher when she goes to Yale, but Jamie is still her boyfriend. She later feels bad about leading the boy on and breaks up with him when he comes to visit her on his birthday.

Lorelai And Jason

Lorelai and Jason have known each other since they were kids, but they reconnect when Jason comes to Richard, requesting to be his business partner. Jason soon asks Lorelai out, although they don't tell her parents. As their relationship blooms, Jason wants to tell Richard and Emily, but Lorelai still wants to keep it all under wraps.

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Their secret comes out after Jason's father reveals it during dinner with the Gilmores, and soon after, Jason announces that he is suing Richard when their company dissolves. Lorelai breaks up with him, saying she can't date someone who is suing her family.

Rory And Jess

Jess has had his eye on Rory ever since he first came to town, although he has a funny way of showing it. He enjoys annoying Rory's first boyfriend Dean, but Rory is one of the only people in Stars Hollow whom Jess gets along with.

The two share a kiss while Rory is still with Dean, but the latter couple eventually breaks up, leading to Jess and Rory's relationship. They were only together for half a season, and then Jess leaves town when he fails his senior year of high school. He tries to win her over again a year later, saying he's more mature now, but she says no.

Lorelai And Max

Max is Rory's teacher at Chilton, and he very soon becomes Lorelai's boyfriend. They have a somewhat complicated relationship, with Lorelai going back and forth between not knowing if she wants to be with him and worrying about how it will affect Rory.

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Things move pretty fast between them, and Max proposes not too long after their relationship starts. They plan a whole wedding together, and then Lorelai backs out right before it's time to tie the knot.