Gilmore Girls centered on our favorite mother/daughter duo as we saw Lorelai and Rory navigate through life's ups and downs. Additionally, they often had to navigate through prickly family situations with Lorelai's parents and Christopher, Rory's father.
The mother and daughter generated enough humor to get them through challenging times. Still, they (as well as other characters) had a fair share of heartbreak throughout the show's seven seasons and the A Year in the Life special. Their heartbreak became our heartbreak as we watched our loved characters face obstacles.
10 Dean Dumps Rory In Front of the Town
Dean was Rory's first boyfriend and love. While it's true that she had feelings for Jess at this time, Dean could have handled it better. Instead, Dean dumps Rory in Season 3 at the Dance-a-thon in front of the whole town, saying, "I'm tired. I'm over it."
Lorelai consoles a crying Rory and no longer cares to win the dancing contest. While we were ready for Rory to be with Jess and no longer with Dean, we still felt for Rory at this moment.
9 Taylor Not Getting Votes
It's true that Taylor was often irritating, and we liked when Jackson ran for town selectman instead. As irritating as Taylor was, we realized that he both really cared about the community of Stars Hollow and aligned part of his identity with being town selectman. So knowing that there was going to be a landslide where only one person (Taylor himself) was going to vote for him, we understood Lorelai's mercy. When she learned this, she encouraged more people to vote for him so it didn't look quite as bad. Then Taylor could lose with dignity.
8 Richard in the Hospital
In Season 1, Richard (Lorelai's dad), ended up in the hospital due to a heart attack. Lorelai panicked, and Luke drove her there, looking after her. Still shaken up, she puts off speaking to her father. Instead, she looks for coffee and insists that Rory keep him company. She realizes that she hasn't been alone with her dad much and isn't sure what to say to him. In addition, she realizes that she came close to losing her father. This thought is enough to get to her, and it takes her a while to breathe easily.
7 Lorelai Isn't Ready to Marry Max
Max, a teacher at Rory's high school, was a good match for Lorelai. He was smart, caring, loving, and got along with Rory. Additionally, Rory was looking forward to being his stepdaughter.
When Lorelai goes out for her bachelorette party, Emily, her mother, waxes poetically about how certain Emily was about marrying Richard. Lorelai realizes that she isn't nervous or anticipating her wedding. Actually, she seems to be dreading it. The one person she wants to call during the party isn't Max, but Christopher, her ex and Rory's father. Later, she breaks up with Max. It seems that Max and Lorelai may have moved to marriage too fast, and they could have worked out had they taken it more slowly. Still, it is a painful moment when Lorelai realizes that as much as she feels she should want to be married to him, she doesn't.
6 Christoper's Parents And The Aftermath
In Season 1, Emily and Richard include Christopher and Christopher's parents in the weekly dinner that they have with Lorelai and Rory. It is an attempt to be together like one big family, orchestrated by Emily and Richard. Rory is clearly nervous, self-conscious, and excited to meet her other grandparents. Richard begins by talking up Rory, about how good a student she is, and how proud they are of her. When Christopher's father begins to criticize Lorelai for ruining his son's life 16 years ago by getting pregnant, Lorelai wisely tells Rory to leave the room.
Christopher's father continues to insult Lorelai. Then he becomes even crueler by referring to Rory as "that baby," and "that girl," rather than calling her his granddaughter. The dinner ends with Richard standing up for the Gilmore name and defending Lorelai. From there, Lorelai and Rory have two very different experiences. Lorelai thanks Richard, and he "thanks" her by telling her how much of a disappointment she was to them when she got pregnant, dropped out of school, and moved away. Emily finds a sad Rory and tells her that Rory has never been a disappointment to any of them.
5 Lane And Mrs. Kim Fighting
In Season 7 Mrs. Kim and Lane fight about how to raise her twins once they are born. It seems a fight that could end their mother/daughter relationship as both are stubborn and insist on their sides. This part breaks our heart because while Mrs. Kim and Lane don't have the same type of mother/daughter relationship as Lorelai and Rory, they still love each other.
Luckily, Lorelai comes to the rescue, helping Mrs. Kim compromise and stay in her daughter's life. Lane also compromises and tells her mother how much she respects her. Our heartbreak moment ended in a heart melt moment. However, if it weren't for Lorelai, this wouldn't have happened.
4 Luke Excluding Lorelai From April
In Season 5, Luke learns that he has a preteen daughter, April, from a previous girlfriend. His previous girlfriend had kept the information from him. Luke seems to follow suit, keeping the information from Lorelai, whom he is dating. When Lorelai finds out, he doesn't want her to meet April. He fears that April will like Lorelai more than him. While that is also sad, we mostly feel for Lorelai in this situation. They're finally together, but Luke finds excuses to keep them apart and exclude her from important parts of his life.
3 Logan's Dad Judges Rory
All of her life, Rory has wanted to be a journalist. Goal-driven, Rory worked hard to get where she is. When Logan's dad, a prominent person in the field, offers her an internship, she jumps at it. Then he puts her down, saying that he knows when people have got it, and she doesn't. Later, when she becomes a success, he actually claims responsibility for it.
This is laughable because his statement led to her stealing a boat, being put in jail, dropping out of college, fighting with her mother, living with her grandparents, becoming part of the world her mother tried to save her from, and generally, being a shadow version of herself. Still, maybe that rejection did make her stronger in a sense, although it was hard for us to see Rory judged and rejected that severely.
2 Rory And Lorelai's Fight
While Rory and Lorelai have had fights and spats in the show, the fight after Rory left Yale goes down as the worst in their history. To make it worse, Richard doesn't follow through on being on the same team with Lorelai to get Rory back in Yale. Later, Richard regrets this, realizing that Lorelai was right all along.
Lorelai knows that Rory can do better and that leaving Yale is a mistake. She refuses to coddle Rory or let Rory live back at home. Mother and daughter don't talk for a long time. Whenever they do see each other, it is tense. When their fight was over, we were relieved, but it took more episodes than we would have liked.
1 Richard's Death
A Year in the Life begins with Lorelai, Rory, and Emily grieving Richard. They try to process and grieve in their own ways. Emily has a comically large portrait of Richard made. Lorelai spends the whole year trying to process things. Rory stares at Richard's desk, noticing the big absence of him. They all grieve, trying to make sense of their lives without Richard there. Add to this the fact that the actor Edward Herrman, who played Richard, really did die, makes our hearts break even more.
Gilmore Girls gave the heart feels and the heartbreaks, a journey worth taking in the end.