Top 10 Saddest Gilmore Girls Moments
#10: Christopher Leaves... Again “I Can’t Get Started”
For fans of the couple, Lorelai and Christopher’s teary split in Season 7 is a hard pill to swallow. But the Season 2 finale takes the cake for the pair’s saddest moment. When Rory’s dad abruptly returns to Stars Hollow, there’s room for him and Lorelai to rekindle their age-old romance. But his recent partner Sherry’s surprise pregnancy forces him to call it quits by the end of the episode. After seeing him and Lorelai contemplate a true reunion, it’s horrible to see her get dumped — and at a wedding, no less. He’s certainly in a tough position. But the departure painfully mirrors his absence during Rory’s childhood. To make matters worse, Lorelai must immediately bury her feelings to participate in Sookie’s nuptials.
#9: Rory’s Wallowing “The Breakup, Part 2”
Top 10 Rory Gilmore Moments That Make Us Yell at Our TVs
Rory’s been embroiled in relationship drama from the first season of “Gilmore Girls”. Early on in the series, her painful split from Dean was the talk of the town. Unfortunately, her attempt at a quick recovery goes south after she surprisingly shares a kiss with Tristan at a Chilton party. In the final scene, Rory is found truly feeling the weight of her loss at home. It’s a hard saga to watch because she and Dean seemed to be a rock-solid couple. The show’s depiction of teen heartache is all too relatable. Thankfully, Rory happens to have one of TV’s coolest moms to comfort her through the wallowing.
#8: Emily & Richard's Separation “Say Goodbye to Daisy Miller”
Top 10 Most Savage Emily Gilmore Moments
Season 5 opens with an emotional storyline that we didn’t see coming. In the premiere, Emily and Richard are bickering non-stop and decide to split up. Seeing the elder Gilmores duke it out so fiercely and even move into separate quarters is a new and alarming development. With both parties reluctant to reconcile, an end to the feud is nowhere in sight… until a lost dog stumbles into their lives. The road to their vow renewal is rocky to say the least. We even watched Emily break down after a date with another man. After a sad separation, we were glad to see the old-fashioned couple end up stronger than ever.
#7: Rory & Dean's Second Breakup “They Shoot Gilmores, Don’t They?”
Top 10 Times Rory Was the WORST on Gilmore Girls
One of Rory’s major plotlines in Season 3 finds her at the center of a tempestuous love triangle. While dating Dean, she often clashes with bad-boy Jess. But there’s something about their connection that her boyfriend Dean doesn’t like. After Jess makes a scene at Stars Hollow’s dance marathon, Rory clearly can’t stop thinking about him. Unfortunately, her preoccupation is a bit too suspiciou and she gets dumped in the middle of the dance floor. Seeing Rory cradled in her mother’s arms is definitely an eye-watering sight. But perhaps the saddest part is the fact that Dean put up with a one-way relationship for far too long.
#6: Lorelai Sings Karaoke “Lorelai? Lorelai?”
Top 10 Unforgettable Luke & Lorelai Moments
Luke and Lorelai go through more than their fair share of ups and downs on “Gilmore Girls.” Even after they’ve finally gotten past their messy break-up at the tail end of Season 7, their future is still uncertain. Since they encountered so many obstacles to getting married while hurting each other in the process, it’s hard to say whether they’ll give it another shot. But Lorelai’s intentions become heart-wrenchingly clear after she invites Luke to a karaoke bar. While in the midst of singing Dolly Parton’s “I Will Always Love You,” Lorelai’s tone of motherly pride morphs into obvious romantic longing for her ex. Aside from being beautifully done, the tear jerking scene is chock-full of bittersweet nostalgia for the past.
#5: Rory & Lorelai's Estrangement “A House is Not a Home”
What If Rory Had Stayed With Jess?
At the end of Season 5, Rory embarks on several decisions that lead to that devastating rift between her and her mother. After getting into trouble with the law, she decides to drop out of Yale and turns to Richard and Emily for support. A betrayed Lorelai shockingly cuts off contact with her daughter. There are few moments in the show as heartbreaking as the mother and child sharing a glance through the Gilmores’ guest house window. As much as we wanted them to, they made no move towards reconciliation. Seeing the show’s central duo go from best friends to barely speaking is a truly devastating turn that we didn’t see coming.
#4: Mrs. Kim Kicks Lane Out “In the Clamor and the Clangor”
While Lane Kim and her mother have a great deal of conflicts, things truly come to a head in this fourth-season episode. As Lane’s commitments to her band begin to outweigh her daughterly obedience, she makes the ill-advised decision to sneak out. Mrs. Kim is understandably scared and clearly hurt when she finds out both Lorelai and Luke were informed before her. This incident leads her to discover Lane’s stash of rock and roll paraphernalia. Lane sees this as an opportunity to start fresh on a more honest footing, but unfortunately Mrs. Kim is not on board with her suggestions. It’s truly devastating to see the teen’s hopes for an improved relationship be dashed with just a few words.
#3: Richard's Death “Winter”
The first installment in the show’s revival “A Year in the Life” finds the characters going through one of their most harrowing experiences. Richard’s passing weighs heavily on all three Gilmore girls and has led to some serious tension between Lorelai and Emily. After watching a flashback, we understand why. Lorelei flubbed a tribute to her dad after his funeral and her mother still hasn’t forgiven her for it. For her part, Emily is listless in the wake of being widowed. The episode shows how hard honoring a loved one who has gone too soon can be. Outside of the show, Richard’s actor Edward Herrmann passed away in 2014. Knowing that this episode is dedicated to him made “Winter” all the more heart-wrenching.
#2: "Yes Emily, You May Go First" “Forgiveness and Stuff”
Top 10 Gilmore Girls Moments
One of the scariest moments for the Gilmore family happens in the show’s tenth episode. After Richard collapses from a heart attack off-screen, Lorelai meets her mom at the hospital. Emily is definitely on edge the entire time. After finally getting a moment with her husband, she wants to talk bedsheets while his mind is on more serious matters. Eventually, with tears in her eyes, Emily makes him promise that he’ll outlive her. We were relieved to see Richard okay after the health scare. However, this was still one of the couple’s most bittersweet moments. Before we unveil our top pick, here are a few honorable mentions. Rory & Jess’s Breakup, “Those Are Strings, Pinocchio” His Inability to Speak Up Makes It Clear Why Their Break-Up Should Be Permanent Lorelai’s Financial Troubles, “The Incredible Shrinking Lorelais” She Has an Emotional Breakdown While Asking Luke For Help Rory Misses Lorelai's Graduation, “Lorelai’s Graduation Day” The Younger Gilmore’s Ill-Fated Decision to Skip Town Makes Her Mom Very Upset Rory’s Graduation Speech, “Those Are Strings, Pinocchio” It’s Bittersweet Knowing Our Favorite High-Schooler Will Soon Fly the Coop Paris’s “C-SPAN” Breakdown, “The Big One” It’s Hard to Watch This Perfectionist Publicly Succumb to the Pressures of College Applications
#1: Lorelai's Post-Breakup Phone Call to Luke “Say Something”
Although Lorelai endures several break-ups over the course of the series, her Season 5 split with Luke is truly devastating. After Emily plants doubts in Luke’s mind at her own vow renewal, the latter says he needs time to think about the relationship. He eventually decides to call it quits. This turn leaves Lorelai as a bedridden wreck. At one point, she shows astonishing vulnerability when she leaves him a rambling voicemail about the movie “The Way We Were”. Since the young mom is typically full of peppy energy, it’s hard to see her so deeply despondent. The only silver lining is that this separation is relatively short-lived.
