With Gilmore Girls being a family drama, there were as many sad episodes as there were optimistic ones. Lorelai Gilmore has a tumultuous family background, which was a major source of tension and sadness throughout the series. Since Rory was a beloved member of the Gilmore family, he was divided between two worlds: his grandparents’ and his mother’s. But it wasn’t all family matters that gave this show sad episodes.

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Relationship problems also affected most of the characters. From young love to divorces, the people of Stars Hollow were heartbroken multiple times. After seven seasons of falling in love with the show’s characters, it’s easy to get as excited as they are when they go through something traumatic.

10 “In the Clamor and the Clangor” (S4, E11)

Gilmore Girls - In The Clamor And The Clangor

In “In The Clamor and the Clangor” from season 4, Ms. Kim finally discovered Lane’s big secret: her identity. Lane has kept her true passions a secret from her mother since she was six years old. She knew her mother wouldn’t approve of her.

When Ms. Kim discovered everything Lane was hiding, Lane was relieved that the secret had come out. However, Ms. Kim was distraught and kicked her daughter out of the house. This was a huge turning point in Lane and Ms. Kim’s relationship and it was heartbreaking to see their hearts break.

9 “Say something” (S5, E14)

GILMORE GIRLS - Say something

“Say Something” was one of Lorelai’s most emotional episodes. His parents just renewed their vows in the previous episode and it ended with Luke dating alone. In this episode, Luke told Lorelai that he needed some time to think about what he wanted, but after she bothered him, he admitted that it wasn’t going to work. Christopher, Emily, and Richard were always going to be in his life, and that was a life he couldn’t be a part of.

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Watching Lorelai cry herself to sleep and leaving a heartbreaking voicemail for Luke was too much for the viewers.

8 “I can’t start” (S2, E22)

Chris and Lorelai at Sookies Wedding - Gilmore Girls

“I can’t start” he began with such a promise. Christopher came to town to see Rory take off the cast and things seemed different between him and Lorelai. Christopher and Sherry broke up and he was looking for a second chance with Lorelai. Rory was excited for both of her parents to give their relationship a second try, but as soon as they started, they ended.

At Sookie’s wedding, Christopher discovered that Sherry was pregnant with his son. Just like years ago, he left Lorelai and Rory once again to start a different life. It wasn’t just Lorelai who felt betrayed; Rory did too.

7 “The Incredible Sinking Lorelais” (S4, E14)

GILMORE GIRLS - The Incredible Sinking Lorelais

“The Incredible Sinking Lorelais” was a difficult episode for both Lorelai and Rory. It was great to show the parallels between mother and daughter. For Lorelai, the inn was nowhere near completion and she ran into money problems.

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The only person she could turn to was Luke. But asking her friend for $ 30,000 was a lot of money, and she broke down in tears when he asked. Likewise, Rory was struggling with the load of his course and couldn’t keep his head straight. After meeting Dean, Rory collapsed into his arms from stress. It was moving to see them fall apart at the same time without the other knowing.

6 “Sorry and stuff” (S1, E10)

sorry and stuff - gilmore girls - christmas

In “Sorry and Stuff,” Richard suffered a serious heart attack and landed in the hospital. The impact of her poor health was too much for Emily to handle and she began to misbehave in the hospital. Understandably, he wanted Richard to be treated like a king.

When Richard was awake, Emily and Richard had an emotional conversation. “I did not aim for your death. And it will not happen. Not tonight, not for long. In fact, I demand to go first. Is that clear? “Emily told Richard with tears in her eyes. Adorably, Richard knew how difficult this was for Emily and said,” Yes, Emily. You can go first. “

5 “A house is not a home” (S5, E22)

gilmore girls - a house is not a home

Nobody likes the fall of Lorelai and Rory and it is in “A house is not a home” when it happens. In the episode, Rory takes her final exam before summer break after being recently arrested for stealing a yacht. That’s when he realizes that he wants to quit school. After telling her mother, Lorelai went straight to Richard and Emily for support; Rory needed to finish college.

The Gilmores supported Lorelai 100%, but as soon as Rory reached out to talk to them, they switched sides. At the end of the episode, Lorelai found out that it was three against one and that Rory would now be living with the Gilmores. It was incredibly painful.

4 “Richard in Stars Hollow” (S2, E12)

In “Richard In Stars Hollow”, Richard had just retired and was learning to be a man who did not work. It was hard for him to relax and do nothing. Emily was the first to point out how annoying she found him when he was around all the time, so she sent him to Stars Hollow for the day.

Sadly, even Lorelai and Rory found it to be an arduous task. At the end of the episode, Richard told Emily that he knew exactly what she, Lorelai, and Rory were doing. He didn’t realize that no one wanted him around until he had time to be around. Seeing her sadness was heartbreaking for viewers.

3 “The party’s over” (S5, E8)

rory and emily gilmore

Fans of #TeamDean were thrilled when Dean and Rory got back together after their divorce from Lindsay. But their sweet relationship fell apart on “The Party’s Over.”

When Emily found out that Rory was dating her high school sweetheart again, she stepped in and threw a Yale alumni party where she only invited eligible kids Rory’s age who were attending Yale. With Logan there, Rory drank too much champagne and ended up making a scene when he left the house to see Dean. Seeing Rory with a trail of men behind her, Dean knew that he and Rory were no longer together. He broke up with her and left crying.

two “Christopher’s Return” (S1, E15)

GILMORE GIRLS - Christopher's Return

Christopher returns to Hartford with his parents in “Christopher’s Return.” He and his parents dine with Rory, Lorelai, and their parents as a way to re-blend as a family. Sadly, the night turned sour when Christopher’s parents went after Lorelai for ruining their son’s life (did they forget that it takes two to tango?) Richard had no choice but to defend Lorelai and represent Gilmore’s name. . He expelled the Haydens.

Later, Lorelai went to her father’s office to thank him for supporting her, but things turned dark. Richard protected the family, not Lorelai. He was still mad at her for taking Rory and running so many years ago. Then he knew that Lorelai never really needed him, which saddened him until that day.

1 “Scene in a mall” (S4, E15)

Gilmore Girls - scene in a mall

“Scene In A Mall” is one of Emily Gilmore’s saddest moments. With Richard busy with his new business, Emily felt like she was unable to do anything. The only thing she was known for was buying and spending money. It was heartbreaking to see Emily realize that she had nothing to show for and that her own husband didn’t even care what she did all day. At the end of the episode, Richard is unaware of the apple decorations Emily bought and the expression on her face says it all. It felt unworthy and irrelevant.

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