There are as many sad Gilmore Girls episodes as there are upbeat ones since the series is a family drama. Lorelai Gilmore (Lauren Graham) has a tumultuous family background, which is a major source of tension and sadness throughout the series. With Rory (Alexis Bledel) being a beloved member of the Gilmore family, she became torn between two worlds: her grandparents’ and her mother’s. But it wasn’t all family matters that gave this show sad episodes.

Relationship woes also plagued most of the characters. From young love to divorces, the people of Stars Hollow had their hearts broken on multiple occasions. After seven seasons of falling in love with the show’s characters, it’s easy to get as emotional as they do whenever they go through something traumatic. The saddest Gilmore Girls episodes all feature some sort of heartbreak or goodbye.

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“They Shoot Gilmores, Don’t They?” (S3, E7)

This episode isn’t just one of the saddest episodes of Gilmore Girls; it’s also one of the most emotionally charged episodes of the show. Much of the episode takes place at a dance marathon for charity, and it’s when Dean and Rory break up for the second time. Even though their breakup doesn’t happen until the end of the episode, much of the lead-up is still hard to watch.

At the dance marathon, Rory spends most of her time trading barbs with Jess, which Dean is not oblivious too. At this point in the show, Rory and Jess have spent an entire season dancing around their feelings for one another, and Dean has grown more and more jealous of their connection. It’s sad to watch the love triangle play out in such an explosive way as Dean calls Rory out for her feelings for Jess in front of the entire town and then breaks up with her.

“Emily Says Hello” (S5, E9)

Emily Gilmore isn’t someone who lets her emotional guard down very often. She gets angry, and she gets snarky, but she doesn’t usually let anyone see her vulnerable. That’s why any time she gets particularly emotional in the series, fans are better able to connect with the character. “Emily Says Hello” is one of the saddest Gilmore Girls episodes for that very reason.

In the episode, Emily goes on her first date after being separated from Richard. The two have been together for somewhere around 40 years at that point and Emily, despite the problems in her marriage to Richard, finds it hard to connect with someone else. When she comes home to the house without Richard, she cries because it finally hits her that the two of them are truly separated, and it’s a heartbreaking scene for the show.

“Bon Voyage” (S7, E22)

The season 7 finale is also the series finale of Gilmore Girls until the revival series for Netflix. Saying goodbye to the series is part of what makes the episode such a sad one for Gilmore Girls fans. There are a lot of bright spots in the episode, really making it more bittersweet than strictly sad.

What makes the episode said is that Lorelai and Rory also have to say goodbye. Lorelai has had Rory by her side, or just a short drive away, for Rory’s entire life. It’s incredibly hard to see the two separate, but at least they’re separating willingly. It’s also sad when the realization hits that Lorelai’s parents have missed out on so much time with Lorelai and Rory as they see just how much Rory and Lorelai both have touched the citizens of Stars Hollow.

“The Break-Up, Part 2” (S1, E17)

Dean is Rory’s first boyfriend, and when a show runs for seven years, it’s pretty clear that one character probably isn’t going to have the same boyfriend for the entire run - especially if that character begins the show as a teenager. When Dean and Rory break up for the first time, Rory tries to keep herself busy and not think about it.

Unfortunately for Rory, she continues to see Dean all over Stars Hollow, which gradually causes her to crumble. By the end of the episode, she is “ready to wallow” and tells her mom how much she’s hurting. Her denial and eventual emotional outpouring is what makes “The Break-Up, Part 2” one of Gilmore Girls’ saddest episodes.

“Winter” (A Year In The Life, E1)

Gilmore Girls: A Year In The Life is a revival series set a few years after the events of Gilmore Girls. The series itself is hopeful, finally bringing Luke and Lorelai to the same page in their relationship and seeing Emily Gilmore figure out what she wants to do at this stage of her life. “Winter” is the saddest of the Gilmore Girls: AYITL episodes though as it details Richard Gilmore’s funeral.

Funerals, and really any loss of life, are rare in the Gilmore Girls series, though they are a natural part of life. “Winter” is so sad because it reminds the audience of that fact. Emily, Lorelai, and Rory are all grieving Richard in their own way. To top it off, Lorelai and Emily still can’t seem to find common ground even in their grief.

"In The Clamor And The Clangor" (S4, E11)

In season 4's "In The Clamor and the Clangor," Mrs. Kim finally found out about Lane's big secret: her identity. Lane has been keeping her true passions a secret from her mom since she was six years old. She knew her mother wouldn't approve of her.

When Mrs. Kim found everything Lane was hiding, Lane felt relieved that the secret was out. However, Mrs. Kim was distraught and kicked her daughter out of the house. This was a huge turning point in Lane and Mrs. Kim's relationship and it was distressing to see both of their hearts break.

"Say Something" (S5, E14)

"Say Something" was one of Lorelai's most emotional episodes. Her parents just had their vow renewal in the episode prior, and it ended in Luke walking out alone. In this episode, Luke told Lorelai he needed some time to think about what he wanted, but after she pestered him, he admitted it wasn't going to work. Christopher, Emily, and Richard were always going to be in her life, and that was a life he wasn't able to be a part of.

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Watching Lorelai cry herself to sleep and leave a heartbreaking voice message for Luke was too much for viewers to handle, and easily made this rank among the saddest Gilmore Girls episodes.

"I Can't Get Started" (S2, E22)

"I Can't Get Started" started out with such promise. Christopher came into town to watch Rory get her cast off 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 to have both of her parents give their relationship a second try but as soon as they started, they ended.

At Sookie's wedding, Christopher found out Sherry was pregnant with his child. Just like he did years ago, he left Lorelai and Rory yet again to start a different life. It wasn't just Lorelai who felt betrayed; Rory did too. It felt like Christopher became worse as Gilmore Girls continued and repeatedly let them down.

"The Incredible Sinking Lorelais" (S4, E14)

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

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 as she asked him. Likewise, Rory was struggling with her course load and wasn't able to keep her head on straight. After running into Dean, Rory crumbled in his arms from stress. It was tear-jerking seeing them fall apart at the same time without each other knowing.

"Forgiveness And Stuff" (S1, E10)

In "Forgiveness and Stuff," Richard suffered a serious heart attack and landed in the hospital. The shock of his failing health was too much for Emily to handle, and she started acting out at the hospital. Understandably, she wanted Richard to be treated like a king, but the not knowing if Richard would be okay took its toll and made for one of the saddest Gilmore Girls episodes.

When Richard was awake, Emily and Richard had an emotional heart-to-heart. “I did not sign on to your dying. And it is not going to happen. Not tonight, not for a very long time. In fact, I demand to go first. Do I make myself clear?” Emily told Richard with tears in her eyes. Adorably, Richard knew how hard this was for Emily and said, “Yes, Emily. You may go first.”

"A House Is Not A Home" (S5, E22)

No one likes the downfall of Lorelai and Rory, and it's in one of the saddest Gilmore Girls episodes, "A House Is Not A Home" when it happens. In the episode, Rory takes her final exam before summer break after recently being arrested for stealing a yacht. It's then that she realizes she wants to drop out. After telling her mother, Lorelai went straight to Richard and Emily for backup; Rory needed to finish college.

The Gilmores supported Lorelai 100% but as soon as Rory came over to talk to them about it, they switched sides. By 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.

"Richard In Stars Hollow" (S2, E12)

In "Richard In Stars Hollow," Richard had just retired and was learning how to be a non-working man. It was hard for him to relax and not do anything. Emily was the first one 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 him to be a chore. By 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 his sadness was harrowing for viewers.

"The Party's Over" (S5, E8)

#TeamDean fans were thrilled when Dean and Rory got back together after his divorce from Lindsay. But their sweet relationship came crashing down in "The Party's Over."

When Emily found out that Rory was dating her high school sweetheart again, she intervened and threw a Yale alumni party where she only invited eligible boys Rory's age who attended Yale. With Logan there, Rory had too much champagne and ended up making a scene when she left the house to see Dean. Watching Rory with a trail of men behind her, Dean knew he and Rory no longer belonged together. He broke up with her and left in tears, making for their third sad Gilmore Girls breakup.

"Christopher’s Return" (S1, E15)

Christopher comes back to Hartford with his parents in tow in "Christopher’s Return." He and his parents have dinner with Rory, Lorelai, and her parents as a way to mingle as a family again. Fans thought Christopher and Lorelai might actually work out. Sadly, the night went 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 stand up for Lorelai and represent the Gilmore name. He kicked the Haydens out.

Later, Lorelai went to her dad's office to thank him for supporting her, but things got dark. Richard protected the family — not Lorelai. He was still upset with her for taking Rory and running all those years ago. He knew then that Lorelai never really needed him, which saddened him to that day.

"Scene In A Mall" (S4, E15)

"Scene In A Mall" has one of the saddest Emily Gilmore moments, which is what makes it one of the saddest Gilmore Girls episodes ever. With Richard busy with his new business, Emily felt like she wasn't capable of doing anything. The only thing she was known for was shopping and spending money.

It was gut-wrenching to see Emily realize that she had nothing to show for it and that her own husband didn't even care what she did all day. At the end of the episode, Richard doesn't notice the apple decorations that Emily bought and the look on her face says it all. She felt unworthy and irrelevant. It's these small emotional moments that built into truly sad Gilmore Girls episodes.