While Gilmore Girls is widely considered to be a hilarious and sweet show, there are definitely a lot of heartbreaking moments. From couples who split up when they should stay together to Rory’s growing pains, many episodes feature at least one tragic scene that makes fans feel emotional.
From the biggest moments in Rory and Dean’s relationship to the struggles that Emily and Richard go through, there are many parts of Gilmore Girls that are super sad. Fans are sharing the most tragic episodes on Reddit.
“Rory’s Birthday Parties” (S1, E6)
The season 1 Gilmore Girls episode “Rory’s Birthday Parties” breaks fans’ hearts whenever they think about it. While Rory has a wonderful time at the party that Lorelai throws at their home, complete with a new laptop and a cake with her face on it, Emily and Lorelai share an upsetting moment.
Reddit user Weasley9 mentioned that it’s really sad when Emily realizes that Lorelai broke her leg and never told her and tells Richard that she doesn’t know Lorelai at all. The fan wrote, “The way Kelly Bishop delivers that line always devastates me.”
“They Shoot Gilmores, Don’t They?” (S3, E7)
Rory and Dean’s second split might be even worse than the first one, as Rory isn’t totally innocent. Dean realizes that Rory has incredibly strong feelings for Jess and he feels embarrassed.
Reddit user sheherselfandher thinks that this season 3 episode is heartbreaking because “the way Dean broke up with her on that dance floor was hard to watch.” It’s true that even though Dean is in the right here, Rory feels so guilty for the way that she has handled the situation that it’s hard not to feel badly for her.
“A House Is Not A Home” (S5, E22)
For all Gilmore Girls fans, the end of season 5 is a difficult one. Rory not only changes her future by leaving Yale, but she decides to start relying on her grandparents instead of her mom, and Lorelai is left devastated and confused.
For Reddit user chrisched, this is the saddest episode. The fan wrote that this seemed so tragic because of “The ULTIMATE betrayal when Lorelai finds out what Emily and Richard did (Rory dropping out and moving into the pool house).”
“Forgiveness And Stuff” (S1, E10)
The saddest parts of Richard’s Gilmore Girls arc include when he has heart problems in season 1. Every major character is scared during this storyline as they begin to picture a world without Richard.
While Rory is scared since she’s so young and this is the first time that a family member has been sick, Emily breaks fans’ hearts in this episode as she doesn’t want to live without her soulmate. Reddit user loruk1984 thinks that this is a sad episode because of “Emily at the hospital demanding she go first.”
“Bon Voyage” (S7, E22)
Reddit user Twina801 called the season 7 finale “the best tear jerker!” When compared to other episodes, this one is bittersweet, as Rory gets ready to leave home for good and begin her journalism career, and Lorelai has to say goodbye to her best friend and find a way to move forward.
For many viewers, one of the saddest parts of this episode comes when Richard tells Lorelai that she’s amazing because she has connected with so many people in Stars Hollow and they all want to celebrate Rory. It feels like Lorelai has missed out on so much time with her parents.
“Winter” (A Year In The Life, E1)
Gilmore Girls: A Year In The Life has confusing moments, but Richard’s passing and funeral remind viewers of the sad yet inevitable passage of time.
For Reddit user crittab, “Winter” is a super sad episode because the main characters are grieving the loss of Richard. The fan wrote, “Seeing how his death affected everyone is hard to watch.” It’s also difficult to see that Lorelai and Emily are still in a bad place and that they haven’t figured out how to mend their relationship.
“Scene In A Mall” (S4, E15)
In “Scene In A Mall,” Lorelai and Rory run into Emily at the mall and end up having a chaotic if fun time. It’s humorous watching Emily in this setting, but this season 4 episode also shows the cracks in Emily and Richard’s marriage.
Reddit user fikafikafika mentioned the sad moment in this episode when Emily asks Richard if he likes the apples that she bought and he is dismissive. The fan wrote, “The look on her face just breaks my heart.”
“The Break-Up, Part 2” (S1, E17)
Many Gilmore Girls fans remember watching Dean break up with Rory for the first time and seeing Rory try to cope with the emotions. She has never experienced anything like this before and it’s particularly upsetting that she keeps seeing Dean around Stars Hollow.
One Redditor considers this a really sad episode, writing, “when Rory says ‘I’m ready to wallow now,’ that gets me every time.” Several viewers definitely feel the same way, and Lorelai showing Rory to embrace her sadness is one of the most classic moments.
“Emily Says Hello” (S5, E9)
While Emily insults people on Gilmore Girls on a regular basis, viewers can connect with the times when she shows emotions. She has many layers and she might not want people to see her in a vulnerable position, but she does feel insecure sometimes, particularly about her marriage.
Reddit user sheherselfandher wrote that it’s “super painful when Emily comes home and cries alone” because she goes on a date and realizes that she and Richard were really separated.
“Say Something” (S5, E14)
Reddit user Stranger_2000 mentioned the season 5 episode when Luke and Lorelai break up and wrote, “I feel Lorelai’s pain and I can feel every time my heart has been ripped out…”
The fan mentioned that although this couple does reunite, the breakup still stings. There’s something particularly heartbreaking about how little hope Lorelai has for the future of her relationship with Luke as he was once “all in” but now, it seems like he’s slipping away.