‘Gilmore Girls’: 3 of the Show’s Most Heartbreaking Moments

Gilmore Girls wasn’t supposed to be more a comedy than a drama. Most of the time, the series was a feel-good show about a mother-daughter duo navigating life together on their own terms. The series, however, did take dramatic turns every so often. In fact, there were more than a few heartbreaking moments. Do you remember these three heart-wrenching moments from the show’s seven-season run that made viewers feel all sorts of feelings? 

Emily Gilmore’s raw emotion after Rory left is difficult to watch 

Emily Gilmore was an incredibly complex character, and her relationships with both Lorelai Gilmore and Rory Gilmore were equally complicated. While she initially came across as cold and stoic, Emily was rather emotionally fragile. She didn’t show that side of herself often, though. However, when she did, the emotions were palpable. Several incredibly heartbreaking moments involved Emily, but perhaps the rawest came in season 6. 

In season 6, Rory found it difficult to live with Richard Gilmore and Emily. In a moment of complete defiance, she moved out without telling anyone. Emily responded by considering the purchase of a plane. When Lorelai meets her at the hangar, her monologue is perhaps one of the most emotionally raw moments in the entire series. Her final words in the scene, “I lost her like I lost you. Feels remarkably similar to me.”, drove home the point that Emily never really got over Lorelai’s decision to leave Hartford. 

Lorelai obsessing over Paul Anka when he was sick broke viewers’ hearts

Lorelai and Rory might not have been pet people initially, but that all changed when Lorelai adopted Paul Anka during her rift with Rory. She made it her mission to ensure the dog was well cared for and had everything he could ever need. When he fell sick, Lorelai freaked out. That’s not particularly sad, but her tearful insistence that she was a “bad mom” certainly was. 

Reddit users point out that the scene feels so emotionally raw because of the rift between Rory and Lorelai. Lorelai equated being unable to figure out what was wrong with Paul Anka to her failing to help Rory stay on track and in school. In the end, it all worked out, though. Paul Anka got better, and Rory returned to school and reconciled with Lorelai. 

Lorelai congratulating Christopher Hayden on his new baby feels particularly raw 

In season 3, Christopher Hayden’s girlfriend, Sheri, gave birth to the couple’s first daughter. While there is nothing particularly sad about Gigi’s birth when you look at it in a bubble, the backstory makes Lorelai’s sweet congratulations feel especially heartbreaking. Lorelai’s far-off look also clarifies that she was absolutely heartbroken to see Chris move on but knows she was right to let him go. 

Just before Sheri announced her pregnancy, Lorelai and Chris were getting incredibly close. In fact, Chris was ready to call off the relationship and move on with Lorelai. The former flames even slept together. Chris then found out that Sheri was pregnant, and Lorelai told him to be with her so he could be a part of his child’s life. The stiff but genuine congratulations she offered in the episode, “Dear Richard and Emily”, revealed just how heartbroken she was.