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Gilmore Girls: Lorelai’s 12 Most Questionable Life Choices

Part of Lorelai Gilmore’s charm was how she lived by the seat of her pants. She followed her heart without much thought and sought to find joy in her life. Serious matters did not suit Lorelai because what’s the fun in being serious? As a single mother and an adult who ran a business, Lorelai had made plenty of mistakes over the years, but some of them were life-altering.

Lorelai’s mistakes typically affected her daughter, Rory, and her day-to-day life in a small town that loved gossip. As much as fans of Gilmore Girls adored Lorelai Gilmore, she’s made some pretty damning mistakes over seven seasons and a revival.


Updated On August 16th, 2022, by Lynn Gibbs: Lorelai Gilmore was an independent woman who deserved a lot of credit for raising a child by herself while also creating her own business. However, that didn’t mean she didn’t make some questionable life choices. Since she got pregnant at the young age of 16, Lorelai grew up with her daughter, which didn’t always make life easier for Rory. In many scenes, Rory had to act as the adult on behalf of her mother. Lorelai did mature as the series went on, and she made things better with those around her, but fans still can’t get over some of these questionable life choices.

Why Did She Marry Christopher On A Whim?

When Lorelai and Christopher dove into their relationship again, it was obvious that Christopher was more into the relationship than Lorelai was. Lorelai practically had to lie to herself that being with Christopher was the right choice.

RELATED: 10 Episodes That Prove Lorelai & Christopher Were Soulmates

When the couple went to Paris for the sake of Christopher’s daughter, he and Lorelai decided the next step in their relationship would be marriage. And that’s exactly what they did: they eloped in Paris while jet-lagged. It was a decision Lorelai didn’t think through, and it came back to bite her. Although Lorelai thought Christopher was her soulmate, they inevitably divorced.

Lorelai Should Have Gone To Her Parents When She Had A Termite Problem

Lorelai felt uncomfortable asking her parents for money because of their tense relationship, but when it came to Rory’s future, Lorelai had no problem asking for a helping hand. As always, whenever Lorelai borrowed money from her mom and dad she paid them back.

Knowing this sense of trust between them, it was questionable why she didn’t feel comfortable asking her parents for a loan to make some home repairs when she was told termites were destroying her home. When Richard and Emily found out about the termites, they offered money happily to help since Rory deserved a safe home. But Lorelai fought them tooth and nail until the end. She made life harder for herself by turning down help.

She Never Thought Of Rory When Dating Max

On Rory’s first day at Chilton, a handsome man asked Lorelai out on a date. Lorelai didn’t want to but she turned him down because she thought it would be inappropriate to date someone who had a child at Rory’s school.

Oddly enough, Lorelai didn’t think of that logic when she started dating Rory’s English teacher without asking or telling her. What’s worse was when they got engaged and called off the wedding without telling Rory why. Rory was pulled through the mud without Lorelai thinking about how it affected her at school.

She Slept With Christopher On The Night She And Luke Broke Up

There wasn’t anything more childish than when Lorelai ran straight to Christopher when she and Luke broke off their engagement. Luke needed more time to think about the ultimatum that Lorelai threw his way, but that wasn’t what she wanted to hear.

Instead of going home after the breakup, Lorelai ran to Christopher’s apartment and slept with him. Not only did Lorelai complicate her feelings between both men, but she made Christopher think he had a chance with her again. At the end of the day, nobody won from this decision, and it was one of the saddest things for Luke.

Did Lorelai Only Propose To Luke Because She Was Sad?

When Rory was arrested for stealing a yacht, she seemed unfazed after leaving the local jail. She was concerned about Logan and downplayed the entire situation, which horrified her mother.

After that awful night, Lorelai went straight to Luke’s where she did something no one expected: she proposed. It was clear that Lorelai was troubled and acting on an impulse. She adored Luke, but she proposed on a whim to be happy again. Luke saw through Lorelai’s gesture but agreed to marry her because he loved her. It was the start of their best character arc.

She Dissed Her Mother In A National Magazine

In the episode ‘To Live and Let Diorama,’ a travel and leisure magazine did a feature interview on Lorelai and the success of the Dragonfly Inn. The fact that the inn was considered one of the best on the East Coast was a huge accomplishment.

RELATED: 10 Saddest Things About Emily Gilmore On Gilmore Girls

However, during the interview, Lorelai bad-mouthed her mother after the reporter asked if her family had any influence on the warmth of the inn. Lorelai said horrible things about Emily and never told the reporter they were off the record. This meant that the reporter added every horrible thing Lorelai said. This was one of the saddest moments for Emily, who was crushed when she read the article.

Lorelai Didn’t Always Make The Best Decisions As A Mother

Lorelai made some hard decisions at a young age when she got pregnant with Rory. By the time Rory was one-year-old, Lorelai ran away from home to raise her alone in Stars Hollow. She had no financial help and lived in the shed behind the Independence Inn. Luckily, the good people of Stars Hollow pitched in and practically raised Lorelai and Rory.

As hard as Lorelai worked at raising her daughter, she didn’t have many boundaries and complicated things from time to time. Rory was too involved with all of Lorelai’s boyfriends and Lorelai got upset whenever Rory did things without her. There was no doubt that Lorelai loved and adored her daughter, but she was ignorant of how her choices affected Rory.

Her Teenage Years Sound Like Logan’s

Lorelai never liked Logan when he started dating Rory. She hated how he and Rory started their relationship and didn’t like that his family’s lifestyle resembled her parents. Lorelai feared Logan would be just like her parent’s country club friends — and he was.

However, what she failed to forget was that her upbringing was similar to Logan’s. She snuck boys in and out of her bedroom window, she drank her parents’ alcohol, and she resented Richard and Emily. All those things are very on-brand with Logan Huntzberger. Lorelai should have recognized this and gone easier on him.

She Never Told Rory That She And Luke Were Engaged (Or That She And Christopher Were Married)

Lorelai had this habit of making huge life changes and not telling anyone about them. She knew she was going to be judged for her behavior, so she hid it from those she loved until she couldn’t anymore. However, nothing was worse than when Lorelai hid those decisions from Rory.

Lorelai never told Rory that she and Luke’s relationship timeline took them to an engagement. Likewise, she never told Rory that she and Christopher were married. Rory was constantly thrown off when her mother made massive life changes without consulting her.

Ghosting Max

Max Medina was a great partner to Lorelai, but she shouldn’t have accepted his proposal because it was unexpected and ultimately came from fear of losing their relationship.

RELATED: 5 Ways Max & Lorelai Were Good Together (& 5 They Never Made Sense)

The couple wasn’t together long enough and didn’t have serious conversations. He had no role in Rory’s life besides being her teacher and he and Lorelai couldn’t agree on where they would live. Alas, Lorelai strung him along and planned an entire wedding before calling it off without much of an explanation.

She Hid Her Friendship With Christopher From Luke

No matter who Lorelai dated, she had to be honest with them about her relationship with Christopher. Christopher was always going to be a big part of her life because of Rory. Hiding her relationship with him only made her look worse, even when her intentions were good.

She also did this with Luke. Luke eventually wasn’t sure if he could trust her because of her shady behavior. This came to light when Luke found out that Lorelai went to Christopher’s house to drink tequila together while they were dating. While it was a great episode for Christopher and Lorelai fans, it was suspicious and disrespectful to Luke.

She Should Have Taken Her Father’s Help With The Dragonfly Inn

Once Lorelai got the Dragonfly Inn off the ground, Richard thought it was best for her to expand her business. He introduced her to a few people that were able to take the Dragonfly Inn to the next level. She would have more connections, more business, and she’d be able to travel more.

Instead of jumping into Christopher’s arms after her breakup with Luke, she should have chosen this incredible experience that was given to her by her dad. Richard had some wise quotes and opportunities for Lorelai that were often ignored.

NEXT: 10 Of The Wisest Quotes From Richard Gilmore On Gilmore Girls

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