There are some relationships on Gilmore Girls that seem totally meant to be. Fans loved watching Rory and Logan meet at Yale, Luke and Lorelai were destined to find each other in Stars Hollow, and Emily and Richard had a wonderful marriage.

While fans were heavily invested in all of Rory and Lorelai’s romances, and the other characters had some interesting developments in their dating lives as well, some relationships didn’t seem like they would work out in the long run. Fans felt badly for these characters, but these breakups made perfect sense.

10 Lane And Dave

Lane met Dave in season 3 of Gilmore Girls and fell for him hard and fast when he joined the band she shared with Zack and Brian. She was thrilled to find out that he felt the same way and they began dating.

Even though these two characters were super sweet together, fans could tell that they would split up, since Mrs. Kim didn’t want Lane to date someone who she didn’t approve beforehand. The rigid rules that Lane lived her life by made her high school relationships tricky, and she broke up with Henry because it was too hard to see each other. When Dave slowly faded away, fans weren’t that surprised, although they missed this charming character.

9 Lorelai And Jason

Lorelai was genuinely excited about dating Jason, and even she was surprised by her feelings, since he worked with her dad and was part of that world.

Fans can see the pros and cons of Lorelai and Jason’s relationship, but it definitely seemed like they would only date for a brief period of time. There were many issues, from Jason not wanting to sleep in the same room as Lorelai to the fact that he sued Richard.

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8 Rory And Dean

Rory and Dean have a long history on Gilmore Girls. Rory shared how much she appreciated him in the revival, and fans felt the same way, knowing that Dean was a kind first partner for her to have.

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Fans were shocked when Dean broke up with Rory in season 1 and again in season 3. It was harsh when he expected her to say she loved him right away, and no one was certain if he would break up with her because of Jess. But when Rory and Dean broke up after dating again in season 4, it made perfect sense. Dean didn’t fit into Rory’s life and while he was still back in Stars Hollow, she was experiencing Yale, and they weren’t on the same page or at the same life stage.

7 Jamie And Paris

Paris and Jamie’s relationship was a shock to this smart and stubborn character. After meeting him while attending a Washington, D.C. summer program with Rory, Paris developed strong feelings.

Their break-up wasn’t a big surprise, as many high school relationships don’t make it until the first day of college. In this couple’s case, Paris didn’t make up her mind about Jamie until she began dating Asher and Rory convinced her to break up with Jamie in the season 4 episode ‘A Family Affair.’ This relationship was significant and showed Paris that someone could care about her, but it didn’t seem like it would last.

6 Paul And Rory

Paul was a surprising character in A Year In The Life. There were many reasons why he didn’t fit into Rory’s world: she seemed to literally forget about his existence, they rarely saw each other, and she was caught up in her affair with Logan.

When Paul and Rory went their separate ways, it felt like the right decision, one that Rory should have made much sooner. Fans didn’t love watching Paul onscreen and definitely wondered why Rory and Logan couldn’t be in a real relationship out in the open. A younger Rory would be confused by her behavior in these four episodes.

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5 Rachel And Luke

It was exciting to meet Rachel when she came back to Stars Hollow in season 1. Lorelai was immediately envious, and fans wanted to know more of her story as well. It turned out that the bohemian photographer was a world traveler who wanted to see if she was meant to be with Luke.

Fans knew that Rachel would leave town again for a few reasons. For one thing, she could tell that Lorelai and Luke were deeply in love. For another, she was a free spirit who didn’t want to live in the same place all the time, and she and Luke could never get past his homebody ways.

4 Sherry And Christopher

Sherry and Christopher began seeing each other in season 2, even becoming engaged and becoming parents to their daughter Georgia, known as Gigi.

Sherry was never a fan favorite character and didn’t fit into Rory and Lorelai’s world. She proved she was self-centered and flaky when she left for Paris, telling Christopher to take care of Gigi. When this romance fizzled out, it wasn’t a shock or something that viewers got upset about. Some people felt that Christopher should be with Lorelai, and many Gilmore Girls episodes focus on the couple. Those who prefer Luke knew that Chris could find someone else.

3 Lucy And Marty

It was nice to see Rory making new friends at Yale, as her high school life was populated with only Lane and Paris. What wasn’t so nice? When Lucy introduced Rory to her boyfriend Marty, who Rory was already good friends with. Marty lied and Rory didn’t tell the truth, either.

It was inevitable that Lucy would find out, and she and Marty didn’t last long after that. No one really thought that this couple would work out, especially since Marty had a huge, obvious crush on Rory, proving that he wasn’t with the right person.

2 Lorelai And Luke

Lorelai and Luke’s romance was both magical and rocky from the start. He saved the fake horoscope she gave him the day that they met, fans knew that they were meant to be together, and the whole town (mostly) supported them.

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Looking back on Lorelai and Luke’s entire relationship through each season, it wasn’t a big surprise that they broke up at the end of season 6. When Lorelai gave Luke an ultimatum asking him to marry her, it was clear that he would say no, as he wasn’t ready yet. Fans knew that Luke was consumed by spending time with his daughter April and he wasn’t giving Lorelai what she needed. Thankfully, this heartbreaking moment was left in the past and the couple got back together and then tied the knot in the revival.

1 Lorelai And Christopher

Lorelai and Christopher danced around each other for several seasons, and it made sense that they would try dating as adults, although viewers were confused when they got married in season 7.

Fans are torn about who Lorelai’s one true love is. Some feel that Christopher loved her more than anyone, and others love how Luke was always there for her. No matter what viewers think about this love story, it did made sense when Lorelai and Chris broke up before the series ended. She wanted to get back together with Luke, and he had to let her go.

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About The Author


Aya Tsintziras
(1737 Articles Published)

Aya Tsintziras is a freelance writer who writes about pop culture and TV. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. She loves coffee, reading, working out, and watching TV. She lives in Toronto with her husband.

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