20 Heartwrenching Gilmore Girls Moments that Brought Tears to Fans

Summary

Gilmore Girls

is a relatable show full of emotional moments that make fans cry, whether happy or sad.

The series offers complex characters and a cozy small-town setting that sets it apart from other shows.

The bond between Lorelai and Rory, the heart of the series, keeps viewers hooked. Gilmore Girls is the quintessential show about life and relationships, encompassing both laughter and tears, happiness and sadness, and lessons learned from mistakes. The imperfect characters and their relatable struggles make the show infuriatingly illogical yet heartwarmingly comforting. Ultimately, it is the mother-daughter bond between Lorelai and Rory Gilmore that makes this series irresistibly rewatchable.

20. Lorelai Cries Herself To Sleep

Gilmore Girls is one of those timeless shows that remains relevant throughout the decades. This series stands out from the rest with its fast-paced storytelling, charming depiction of a small American town, and its compelling and multi-dimensional characters that elicit a range of emotions from the audience. The Gilmores' lives are filled with poignant moments that allow viewers to deeply connect with the characters, some of which are bound to leave them in tears.

Season 5, Episode 14: "Say Something"

19. Mrs. Kim Kicks Lane Out Of The House

Luke and Lorelai's relationship on Gilmore Girls had its fair share of break-ups, but none were as devastating as their split in season 5. After the disastrous vow renewal involving Christopher and Luke, Luke desperately needs time and space to process everything. However, Lorelai resists giving him this much-needed distance. This ultimately leads to their catastrophic break-up, leaving Lorelai shattered and crying in her bed. Witnessing the strong and independent Lorelai crumble over a man, even if that man is Luke, is truly heart-wrenching.

Season 4, Episode 11: "In the Clamor And The Clangor"

Mrs. Kim and Lane's relationship as mother and daughter is far from ideal, primarily due to their starkly contrasting life philosophies. Lane, for her part, chooses to conceal her true identity from her mother, although this façade can only be sustained for a limited period. When Mrs. Kim eventually discovers Lane's clandestine music gigs and other activities, her anger is so intense that she unceremoniously evicts her own daughter from their home, even though Lane has nowhere else to turn to. This particular scene, even in the context of the show Gilmore Girls, is uncomfortably realistic, leaving viewers unsettled.

18. Dean Breaks Up With Rory For The First Time

Season 1, Episode 16: "Star-Crossed Lovers And Other Strangers"

Dean and Rory may appear to be the ideal couple outwardly, but their relationship in Gilmore Girls is plagued with problems right from the start. One major issue is that Dean is significantly more invested in the relationship than Rory. This becomes evident when he confesses his love for her after dating for three months, but Rory is unable to reciprocate. This heartbreaking moment leads Dean to temporarily end their relationship, and Lorelai helps Rory learn how to "wallow."

17. Emily Grieves Her Separation From Richard

Season 5, Episode 9: "Emily Says Hello"

Richard and Emily had a strong relationship for several years, but their resilience is put to the test when a particularly intense argument leads to their separation. Emily embarks on a journey of self-discovery as she learns to navigate life on her own. Taking a bold step forward, she decides to go on a date with another man. Known for her unwavering optimism, Gilmore Girls' matriarch always manages to keep her spirits high. However, upon returning home from her date, she finds herself overcome with sorrow, realizing that her relationship with Richard has truly come to an end. This heartbreaking moment brings tears to the eyes of the viewers.

16. The Gilmores Attend Richard's Funeral

Gilmore Girls: A Year In The Life Episode 1: "Winter"

Gilmore Girls' Edward Herrmann, who played the role of Richard on the show, passed away in 2014. In the follow-up series, Gilmore Girls: A Year in the Life, the first episode titled "Winter" pays tribute to his character's funeral. The impact of this moment is heightened by the knowledge that the loss is not merely fictional, and the exceptional performances by the cast are not solely the result of acting. The sequel delves into Emily's journey as she mourns the loss of her beloved husband, leaving audiences deeply moved.

15. Christopher Leaves Lorelai & Rory Again

Season 2, Episode 22: "I Can't Get Started"

Christopher falls short of being a deserving Father of the Year, as he neglects his responsibilities towards Rory and fails as a supportive partner to Lorelai. Unfortunately, Lorelai gives him another chance, only to realize it was a terrible mistake, as Christopher reverts back to his old ways and abandons her at the first sign of trouble. This scene in Gilmore Girls showcases Christopher's cowardly behavior as he retreats to Sherry, his now-pregnant girlfriend, delivering a hurtful blow.

14. Lorelai Has Money Troubles

Season 4, Episode 14: "The Incredible Sinking Lorelais"

Gilmore Girls season 4, episode 14 showcases a series of poignant moments, one of which involves Lorelai seeking solace in Luke's embrace as tears stream down her face. In this particular episode, Lorelai discovers herself grappling with significant financial difficulties, leaving her with no choice but to turn to Luke for assistance. However, the act of asking a loved one for a substantial sum of $30,000 becomes an arduous and potentially humiliating task, leading Lorelai to a flood of tears. Nevertheless, Luke, being the compassionate gentleman he is, offers unwavering comfort to his dear friend, even amidst the already burgeoning romantic sentiments he harbors for her.

13. Rory Struggles With College

Season 4, Episode 14: "The Incredible Sinking Lorelais"

In the aforementioned episode of Gilmore Girls, Rory encounters a personal predicament. Being a perfectionist, she has become accustomed to excelling academically. Therefore, when she finds herself struggling to manage her course load at Yale, and even receives advice from a professor to drop a class, she becomes distraught. Thankfully, Rory unexpectedly crosses paths with her ex-boyfriend Dean, whom she has always relied on for assistance, and she unloads her troubles onto him. Naturally, Dean is there for Rory, creating a heartwarming moment reminiscent of their shared history.

12. Lorelai & Luke Have Their First Date

Season 5, Episode 3: "Written In The Stars"

Lorelai and Luke's relationship in Gilmore Girls is quite complicated, but they manage to make it work. However, their beginnings, particularly their very first date, are incredibly heartwarming. Fans have eagerly awaited for five seasons to see Lorelai and Luke together, and in season 5, their first date finally takes place. It's a delightful and charmingly awkward experience, but the conclusion is even more remarkable. When Luke wholeheartedly declares to Lorelai that he is "all in," viewers' hearts undoubtedly melt in response.

11. Richard Has A Heart Attack For The First Time

Season 1, Episode 10: "Forgiveness And Stuff"

Richard's health issues begin early on in Gilmore Girls season 1, with his first, and unfortunately not his last, heart attack. The entire family swiftly gathers at the hospital, anxiously standing by Richard's side. The storyline instills a sense of fear, as it is convincingly grounded. In that moment, Emily and Richard share a heartfelt conversation, which becomes all the more poignant when considering Richard's eventual passing in the revival show. He breaks his promise, and Emily does not end up "going first."

10. Emily Regrets Her Life Decisions

Season 4, Episode 15: "Scene In A Mall"

Emily has fulfilled her role as a devoted wife flawlessly, diligently meeting every expectation. However, this realization brings to light the stark fact that she has neglected to pursue other meaningful endeavors in her life. One poignant storyline in Gilmore Girls revolves around Richard's new business, serving as a poignant testament to the heartbreaking truth of Emily's own unfulfillment. Witnessing her gradual realization that even her own husband remains indifferent to her daily activities serves as a harsh reminder of the reality faced by countless women.

9. Richard & Emily Acknowledge Lorelai's Efforts

Season 7, Episode 22: "Bon Voyage"

The finale of Gilmore Girls stimulates a sense of nostalgia unlike any other episode in the series, delivering numerous moments of closure for the characters. Emily and Richard's relationship with their daughter has often been strained, characterized by their usually harsh treatment of her. However, upon arriving at the surprise party in Stars Hollow and witnessing the profound impact Lorelai has had on the lives of those around her, they are finally willing to acknowledge their daughter's accomplishments, fulfilling a lifelong desire for Lorelai.

8. Dean Breaks Up With Rory For The Second Time

Season 3, Episode 7: "They Shoot Gilmores, Don't They?"

The break-up between Dean and Rory for the second time is the most difficult and one of the most heartbreaking scenes in Gilmore Girls. Their relationship has been deteriorating due to Jess, and Dean's intense jealousy towards him. As tensions reach a boiling point during the dance marathon, Dean finally reaches his breaking point. He unleashes his anger and publicly ends his relationship with Rory, which can be seen as quite a jerk move.

7. Richard & Emily Switch Sides

Season 5, Episode 22: "A House Is Not A Home"

Lorelai's biggest issue with her parents revolves around their lack of support for her. This is most evident when Richard and Emily side with Rory. In season 5 of Gilmore Girls, Rory finds herself on a risky path that ultimately leads her to drop out of college. Naturally, Lorelai disagrees with this decision and seeks help from Emily and Richard. Initially, the elder Gilmores align with Lorelai's perspective. However, when Rory shows up, everything changes, leaving Lorelai feeling isolated and betrayed once again by the very same people.

6. Rory Moves In With Richard & Emily

Season 5, Episode 22: "A House Is Not A Home"

After their explosive argument, Rory decides to move out and temporarily stays in her grandparents' pool house. As she unpacks her belongings, Lorelai watches her through the window, creating an emotional scene that tugs at the heartstrings of Gilmore Girls fans. It represents the heart-wrenching fracture in their mother-daughter relationship. Although they eventually reconcile, this particular moment never fails to give viewers goosebumps whenever they revisit it.

5. Lorelai & Luke Break Up Again

Season 7, Episode 1: "The Long Morrow"

In the realm of tormenting its audience, Gilmore Girls takes pleasure in the will-they-won't-they saga of Luke and Lorelai. However, there exists an episode that shatters any hope of their reunion. The moment of heartbreak occurs when Luke pays a visit and delivers a heartfelt proclamation of his readiness for commitment, only to be met with Lorelai's confession of sleeping with Christopher. The devastating blow is intensified by Luke's final gaze at Lorelai before he retreats, leaving a lasting impact every single time.

4. Lorelai Finds Out About Rory & Dean

Season 4, Episode 22: "Raincoats And Recipes"

The storyline in Gilmore Girls featuring Rory and a married Dean is often considered the most controversial in the show. It marks a significant moment where Rory crosses a line and never looks back. Despite Dean's marriage to Lindsay, Rory sleeps with him without remorse. Lorelai, her mother, confronts her daughter, trying to make her understand that this behavior is unacceptable. However, Rory fails to acknowledge her fault, leaving viewers with a sense of something breaking inside.

3. Richard Feels Lonely

Season 2, Episode 12: "Richard In Stars Hollow"

Richard's transition into retirement proves challenging, both for himself and those around him. When Emily reaches her breaking point at home, she urges Richard to visit Stars Hollow and spend quality time with Lorelai and Rory. However, even they struggle to handle his presence. As Richard painfully sits in his chair, he realizes that nobody truly wants his company – a heart-wrenching moment in Gilmore Girls.

2. Lorelai Graduates From Business School

Season 2, Episode 21: "Lorelai's Graduation Day"

Although Lorelai's graduation ceremony is already a heartfelt moment, it would have been even more special if Rory had been there. However, Gilmore Girls allows Richard and Emily to truly shine during this event. The meaningful looks they exchange with Lorelai, who is on stage, convey more than words ever could. They are overflowing with pride for the person their daughter has become, and Lorelai is immensely happy to have her parents witnessing this significant milestone in her professional journey. This particular moment radiates pure wholesomeness.

1. Dean Breaks Up With Rory For The Third Time

Season 5, Episode 8: "The Party's Over"

Rory and Dean's affair leads to their third attempt at a relationship, which proves to be just as unsuccessful as before. Dean is overwhelmed with work, Rory is absorbed in her studies, and both Lorelai and the elder Gilmores strongly disapprove of their romance. It appears that nothing goes right for them. Eventually, during Dean's visit to pick up Rory from her grandparents' house, he acknowledges that their lives are heading in different directions and ends their relationship for good. This moment in Gilmore Girls is hardly surprising, yet it remains disheartening to witness the final chapter of Rory and Dean's relationship.