- The ending of the season five finale
- "The Prodigal Daughter Returns" where Lorelai and Rory finally reconcile. Especially when you consider that Rory's spent the whole episode getting her life back together (talking to her dean, moving out of her grandparents' house, parking herself at the Stamford Gazette until she's given a job) and doesn't call her mom and ask to come home until she's completely got herself back on track doubles as a Crowning Moment of Heartwarming
- I have to go That is all.
- In "Let Me Hear Your Balalaikas Ringing Out" when Lorelai breaks down about how she feels she fails as a mother because of Rory dropping out of Yale and moving in with her grandparents and their subsequent estrangement, while caring for a sick Paul Anka.
- Mom, you've given me everything I need
- The scene between Luke and Jess at the end of 'Teach Me Tonight'. Jess and Rory get into a car accident, leading to Rory breaking her arm and a massive fight between Lorelai and Luke. Luke finds Jess smoking on the bridge, where he sat with Rory during the basket festival, on the verge of tears and sits down beside him.
Jess: "I...I made sure she was ok."Luke: "I know you did."
- Rory's graduation speech
- Rory : Richard and Emily Gilmore are kind, decent unfailingly generous people. They are my twin pillars without whom I could not stand. But my ultimate inspiration comes from my best friend. The dazzling woman from whom I received my name and my life's blood; Lorelai Gilmore. My mother never gave me any idea that I couldn't do whatever I wanted to do or be whomever I wanted to be...As she guided me through these incredible 18 years, I don't think she ever realized that the person I most wanted to be was her. (tearfully) Thank you, Mom. You are my guide post for everything.
- The season three premiere where Lorelai finally breaks down about Christopher leaving her and Rory to go back to his pregnant girlfriend Sherry, because He doesn't want to abandon another child. Lorelai's confessing to Luke about how much Chris's abandonment stings, because he's finally gotten himself together, but it's for another woman and child, is just gut-wrenching.
- Lorelai apologizing to Emily for not telling her about her engagement to Max, explaining that she doesn't know how to tell her things because she's afraid that when something good happens to her, Emily will make her feel bad about it, and that when something bad happens, she's afraid Emily will make her feel worse.
- Rory showing Emily the converted tool shed that Lorelai used to live in before they bought their house, and Emily realizing that her daughter would have rather lived in squalor than with her own parents.
Emily (to Lorelai): You would have lived in the street, in the gutter, in a cardboard box, anywhere as long as you didn't have to be near us, isn't that true?!
- In a first season episode, Richard has a mild heart attack, and Emily, on the verge of tears, berates him for it (although he actually survives).
Richard: Emily, listen. If I die...Emily: No!Richard: Emily...Emily: Richard Gilmore, there may be many things happening in this hospital tonight, but your dying is not one of them.Richard: But—Emily: No! I did not sign on to your dying. And it is not going to happen. Not tonight, not for a very long time. In fact, I demand to go first. Do I make myself clear?Richard: Yes, Emily. You may go first.
- Made all the worse by Edward Herman's death.
- Lorelai finding out about Richard being hospitalized in the diner and the subsequent freak-out are heartbreaking, as is her conversation with Luke in the car about how she has no real happy special memories with her father, and finally her breakdown outside Richard's hospital room after he turns out to be fine.
- Rory and Jess's final goodbye in Season 6. After they kiss, Rory decides to stay faithful to Logan, and leaves. Jess's expression is heartbreaking.
Jess: I guess I'll call Matthew's poet, and have him explain love to me. Poets know all about it, right?Rory: They're supposed to. I'm so sorry I came here.Jess: Don't be. It's what it is...you...me.Rory: [Almost crying] Goodbye Jess. [She walks away]
- Hell, both their expressions are heartbreaking. After everything they went through, its a tragic ending.
- Even worse, remembering that Rory ran away after their first kiss as well.
- When Lorelai graduates from community college, Richard and Emily are obviously deeply moved and very proud. Their sheer joy and emotion is very touching. This scene is also Crowning Moment of Heartwarming. However, Rory's missing this moment seriously clouds the happy picture.
- Lane being told to move out of her house by her mom in the middle of season 4 after telling her that she wants to change the way she lives.
Mrs. Kim: Children do not make the rules. You may... move out and live like that somewhere else.
- Henry "breaking up" with Lane before their first date when he realizes that they can't have a normal relationship. They might have been able to have a chance together if Lane told her mother about Henry, but she realizes it too late to do anything about it.
- From the episode "Jews and Chinese Food", which takes place after Luke and Lorelai's breakup in season 5. During the elementary school production of Fiddler on the Roof, the song "Do You Love Me?" is performed while Luke and Lorelai stand next to each other without saying a single word. It's painfully clear that they want to speak to each other, but since they're fighting, they don't say anything.
- In the season 7 episode, "Farewell My Pet":
Lorelai: You're the man I want to want.Christopher: I know.
- The season 2 finale, Lorelai and Christopher have gotten together at long last, and moments after Lorelai tells an ecstatic Emily and Christopher assures Rory her parents will finally be together:
Christopher: Sherry's pregnant.
- Paris's breakdown after she didn't get into Harvard, especially for viewers who went through the same thing (or are currently in the college app process and fear the same thing happening to them).
- Logan leaving for London
- Rory finding out Logan has been seriously injured and subsequently hospitalised in another stunt.
- Word of God has confirmed that the new miniseries will deal with the death of Richard Gilmore (and its impact on the rest of the family), since Edward Herrmann died in 2014.
- Emily seeks out Mia at the inn. Emily was particularly upset about the fact that when Lorelai ran away, that Mia didn't send her home while Mia decided to take in Lorelai and give her a place to stay. Before she leaves, she asks Mia to not tell Lorelai about the encounter and send her photos of Young Lorelai with Baby Rory.
Tear Jerker / Gilmore Girls
Though It was billed as a light-hearted Dramedy, Gilmore Girls was not without its heartbreaking moments: