Christopher left her.She called off her wedding to Max.Luke broke up with her.
From Season 5, Episode 14: "Say Something"
"Luke. He's gone. He hates me, I blew it."
Jess left town.Logan cheated on her.Dean broke up with her.
From Season 3, Episode 7: "They Shoot Gilmores, Don't They?"
"There's nothing standing in your way now, because I am out."
Lorelai graduated from business school.Rory graduated from Chilton.Rory graduated from Yale.
From Season 2, Episode 21: "Lorelai's Graduation Day"
"I hope Raul's getting enough pictures of Lorelai."
From Season 1, Episode 11: "Paris Is Burning"
"I really, really like you Max Medina."
From Season 5, Episode 18: "To Live and Let Diorama"
"Why doesn't he like me?"
Rory got arrested for stealing a boat.She is overwhelmed with financial trouble.Her father had a heart attack.
From Season 4, Episode 14: "The Incredible Sinking Lorelais"
"This has been my dream forever, and I have it, and it's here and I'm failing."
Her mother-in-law passed away.She had a falling out with Rory.She found out Lorelai is engaged and didn't tell her.
From Season 6, Episode 9: "The Prodigal Daughter Returns"
"I lost her like I lost you."
Her dog, Paul Anka, ate too much chocolate and is very sick.She regrets sleeping with Christopher after a fight with Luke.Rory's leaving in the morning for her new job on the campaign trail with Senator Barack Obama.
From Season 7, Episode 22: "Bon Voyage"
"Mom, you've given me everything I need."
She is finally ready to mourn her first breakup.Her grandparents hate her boyfriend.She got her first F on a paper.
From Season 1, Episode 17: "The Breakup, Part II"
"I'm ready to wallow now."
Christopher's girlfriend just had his baby.Her father is in the hospital.Rory was in a car accident.
From Season 1, Episode 10: "Forgiveness and Stuff"
"Here's where the guy is supposed to give the girl his handkerchief. But I don't have one."
She got in trouble for stealing a boat.She got in trouble sleeping with her married ex-boyfriend.She got in trouble for lying to her friend Lucy.
From Season 7, Episode 10: "Merry Fisticuffs"
It's all Marty's fault, really.
She and Richard are separating.Richard had a heart attack.Richard is having an affair.
From Season 7, Episode 13: "I'd Rather Be In Philadelphia"
"I could lose him, Lorelai. He's my whole life, and there's nothing I can do."