‘Gilmore Girls’: 3 of Lorelai Gilmore’s Cringiest Moments

Gilmore Girls ran from 2000 to 2007, and even though the well-known television series is no longer on the air, the fan base somehow continues to grow. The WB show’s heartwarming character dynamics and quippy dialogue were just some of the reasons so many viewers fell in love with Stars Hollow and Gilmore Girls

'Gilmore Girls' actors Lauren Graham as Lorelai Gilmore and Alexis Bledel as Rory Gilmore in a scene from 'Gilmore Girls: A Year in the Life'
Lauren Graham as Lorelai Gilmore and Alexis Bledel as Rory Gilmore | Saeed Adyani/Netflix

Although many of the show’s fans look at Gilmore Girls as untouchable television gold, there were a few less-than-desirable moments audiences could have done without. Take a look back at what fans say were three of Lorelai Gilmore’s “cringiest” moments. 

The ‘fella’ fail

Though she was cute and caffeinated, being smooth wasn’t necessarily Lorelai Gilmore‘s trademark feature. This definitely was put on blast in an infamous and awkward season two scene. When Lorelai accepted Max Medina’s marriage proposal, it was far from smooth sailing.

In “Red Light on the Wedding Night,” this became abundantly apparent after Max started asking questions about Rory’s curfew and, in relation, his role in Rory’s life. In classic Lorelai fashion, seemingly brushing the topic under the rug, she stated, “Max, Rory’s done. She’s brought up; she’s Rory. You don’t need a role.”

Upset at her response, when Max continued to probe the subject on his role in their life, Lorelai responded, “Well, you’re my fella. You’re my guy, you’re my old man.” Somehow the yikes moment got even worse when she admitted that she hadn’t given their future together much thought but would “start now.”

In a Reddit thread, fans of Gilmore Girls expressed just how much they couldn’t stand this moment. As one user put it, “Lorelai was going to marry him but hadn’t actually factored him into her life in any real way. It definitely was a moment where it was just like … you’re clearly not ready for a real adult relationship.” Well, it is likely that no one was surprised when it didn’t work out.

The questionable rebound date 

Season two of Gilmore Girls might not have been Lorelai’s best. Shortly after recovering from calling the wedding off with Max, Lorelai decided to jump back into the dating scene. Viewers eagerly and cautiously watched as the flirtatious dynamic continued to develop between Lorelai and Paul.

As Screen Rant highlighted, Paul and Lorelai met through night classes for business school. Even though Lorelai knew Paul was a bit on the younger side, she decided to give him a chance. However, that all changed when Lorelai got a glimpse of Paul’s parents and just how young he really was.

Knowing the age difference would be too much, Lorelai backed off, but Stars Hollow didn’t let her get away with dating so much younger. Paul’s time on Gilmore Girls ended in “Run Away, Little Boy,” and the season two episode’s title really said it all. 

The unforgettable fight

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‘Gilmore Girls’: 4 of Rory Gilmore’s Cringiest Moments

Though far and in between, throughout the span of Gilmore Girls, there were some tough times between Lorelai and Rory. The mother-daughter duo that was often more like BFFs were at odds during season six, and things went to the next level in “Always a Godmother, Never a God.” 

During a spout of not speaking, Sookie was hopeful the two would make up when they were forced to come together for Sookie’s children’s baptism. Unfortunately, the beloved chef couldn’t have been more wrong. 

When Lorelai and Rory get into it, instead of trying to bite their tongues until after the ceremony, Lorelai rudely interrupts the baptism. Making matters worse, when Lorelai was scolded for her poorly timed and placed argument, she actually told Rory to take the babies outside with them to continue the fight.

Though Lorelai and Rory were both in the wrong here, Lorelai was the one who couldn’t let go of her frustrations while she was supposed to be acting as godmother.