10 Saddest Things That Happened To Lorelai

Lorelai Gilmore is no saint. She has made plenty of mistakes over the course of her life and has hurt people greatly based on a quick decision that she didn’t think through. She tries to be a better person for her daughter, Rory, but sometimes the 16-year-old in Lorelai comes out instead of a mature, level-headed mom.

RELATED: Gilmore Girls: 10 Things From The Pilot That Would Never Fly Today

On the opposite of the spectrum, Lorelai isn’t always her best to others but she’s had some gut-wrenching things happen to her over the course of Gilmore Girls. From her time as a rebellious teenager to raising a daughter alone, Lorelai did not go through life scathe-free.

10 Her Toxic Relationship With Her Parents



Fans are torn on the dynamic between Lorelai and her parents. Emily and Richard have all the money in the world to put Lorelai on the right track for adulthood. But when Lorelai didn’t want to live by their rules, things became messy. From there on, their bond was broken. The only way Emily and Richard were able to see Lorelai was through bribing her with Friday night dinners for Rory’s tuition.

Every time Lorelai walked into Emily and Richard’s house, it was like a flashback in time for her. The family of three never seemed to put the past in the past. Richard and Emily were always disappointed in Lorelai, and Lorelai always felt like a bother.

9 Rory Missed Lorelai’s Graduation

Lorelais graduation day- gilmore girls

After getting pregnant at 16, Lorelai had to put off college indefinitely. But when she was finally able to dedicate time to her education, she was proud of herself and ready to graduate.

RELATED: Gilmore Girls: 10 Ways Rory Got Worse & Worse

It was a big moment for Lorelai and the only person she wanted at her ceremony was her daughter, Rory. But was Rory there? Nope! She was in wandering around New York with Jesse.

Luckily, Lorelai’s parents were in attendance, but it wasn’t the same.

8 Luke Hid His Daughter From Her

lorelai finds out about april - gilmore girls

Luke and Lorelai were never the greatest communicators early in their relationship. They hid things from each other because they were trying to save their relationship but they ended up hurting it instead.

After Luke reamed Lorelai out for hiding phone calls with Christopher, she promised to be more forthcoming. But when the tables were turned, Luke contradicted himself. He learned that he had a long-lost daughter and never told Lorelai. She had to find out herself and that basically broke their relationship.

7 She Can Never Rely On Christopher

richards hospital bed in gilmore girls

The crazy thing about Christopher is that he’s a mature man with a job and a deep love for both Lorelai and Rory, and yet he’s always absent. Any time he tries to make a comeback it’s always too little too late.

RELATED: Gilmore Girls: 10 Ways Christopher Got Worse And Worse

It’s safe to say that Lorelai never really needed Christopher but she wanted him there when they were together. When they decided to give their relationship a try later in life, Lorelai was all in. But as per usual, Christopher found out his ex was pregnant with his baby, so he left Lorelai to be with them. Lorelai was heartbroken. Later in the series when they were married, Christopher didn’t see Richard in the hospital until far too late. Lorelai needed him and he was nowhere to be seen.

6 She Couldn’t Think Of A Favorite Moment With Her Dad

gilmore gilrs - a year in the life - lorelai on the phone

Lorelai’s father, Richard, sadly passes away in A Year In The Life. As hard as it was for Lorelai, Emily was a puddle. Richard was all she had.

After the funeral, Emily asked a few of Richard’s close friends to share their favorite memory. Lorelai instantly tried to get out of the situation and made up a few meaningless tales at the top of her head. Emily was not impressed. It quickly dawned on Lorelai that she couldn’t think of one fond memory of her father. She eventually dug deep and found one while she was hiking but it was still incredibly emotional.

5 Bamboozled By Her Parents When Rory Left Yale

rory watching tv in the pool house on gilmore girls

It was earthshattering when Rory decided to be affected by Logan’s father and take a break from Yale. Lorelai was against this decision and ran to her parents for the first time in her life and begged them to be on her side. Richard and Emily didn’t understand where Rory was coming from and agreed to support their daughter.

But overnight, their little plan demolished. Richard and Emily ended up supporting Rory’s decision and turned their backs on Lorelai. She felt betrayed by not only her parents but by her closest confidant, Rory.

4 When She Thought She Was Failing

lorelai failing - gilmore girls

In the midst of not talking to Rory, struggling with work, and trying to be a happy person when she wasn’t, Lorelai eventually had her breakdown. When her dog Paul Anka got sick from eating too much chocolate, Lorelai bawled her eyes out because she couldn’t help him. Viewers knew that these tears and emotions were really for Rory, but Lorelai didn’t want to admit it. In another scene, she fell into Luke’s arms and said she was failing in a very upsetting scene.

3 She Was Told She “Ruined Everything”

emily vs lorelai when rory doesnt come home - gilmore girls

On the night of Rory’s first school dance, Emily spent the night at Lorelai’s because Lorelai needed some assistance due to her back spasms. Shockingly, Rory never came home. What’s worse is that Emily was there to see it all. Lorelai was pacing around the house calling Rory’s name while Emily told Lorelai she was a screw-up and that Rory was going to ruin her life, just as Lorelai did.

Lorelai was already panicked and the last thing she needed was to be told she was a disappointment by her own mother.

2 She Drove Herself To The Hospital

gilmore girls - lorelai in labor

When Lorelai became pregnant at 16 years old, her parents wanted her and Christopher to get married immediately. Christopher was willing to go along with it but Lorelai knew it wasn’t right. She was going to raise this baby by herself. Sadly, when Lorelai went into labor, both Christopher and her parents weren’t there. She ended up leaving a note and driving herself to the hospital.

Going into labor is terrifying for any woman but doing it alone at 16 must have been terrifying. It’s sad that Lorelai didn’t have close friends, adoring parents, or a supportive partner at that time.

1 Realizing Christopher Wasn’t For Her

Lorelai wanted her relationship with Christopher to pan out. They’ve known each other since they were kids and had a remarkable connection. But they were always better off as friends. When Christopher proposed in Paris, she knew things weren’t right but forced it anyway. It wasn’t until the two had their first fight as a married couple that Lorelai knew they weren’t going to work.

The realization that she messed up another relationship was big for Lorelai. It was upsetting that it took so long for her to realize the truth.

NEXT: Gilmore Girls: Lorelai’s Boyfriends, Ranked

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Updated: November 4, 2020 — 11:00 pm

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