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Gilmore Girls was mostly about the family dynamics of the Gilmore clan, as well as the quirky town of Stars Hollow and all of its eccentric residents. The show is beloved for being light, comforting, and funny. The town of Stars Hollow and its residents are considered ideal by fans. Still, there appears to be a dark underbelly, just like Paris Geller once predicted. Upon closer inspection, we were shocked to find out how many times the show’s main characters turned up on the wrong side of the law. 

Rory Gilmore stole a boat in season 5 

One of the most notable instances of an arrest on Gilmore Girls occurred when Rory Gilmore found herself in hot water during her time at Yale. In Season 5, Rory, troubled by Mitchum Huntzberger’s assessment of her journalistic talents, talks Logan Huntzberger into stealing a boat with her. 

Logan and Rory dressed in costume for a Life and Death Brigade event in 'Gilmore GIrls: A Year in the Life.' A second 'Gilmore Girls' revival has not yet been announced
Logan Huntzberger and Rory Gilmore | Saeed Adyani/Netflix

The duo were caught and taken to a local lockup, where Lorelai later rescued her. She was sentenced to community service. Logan appeared to get away with the crime without consequences. Rory’s stunt led to her decision to drop out of Yale and an episodes-long rift between Rory and Lorelai. 

Luke Danes was arrested for assaulting a car in season 4 

While Rory’s run-in with the law had the most far-reaching effects of any Stars Hollow lockup, it wasn’t the first. Luke Danes found himself on the wrong side of the law, too. When the diner owner realized he was wearing another man’s socks, he headed to the apartment he was supposed to share with his sort-of wife, Nicole Leahy, to see what was going on. His suspicions were confirmed. Nicole was cheating on him. He opted to assault the car of Nicole’s date as retaliation. 

Scott Patterson as Luke Danes in the "Summer" episode of 'Gilmore Girls: A Year in the Life'
Luke Danes in ‘Gilmore Girls: A Year in the Life’ } Netflix

Things probably wouldn’t have gone further than that if a nosey neighbor hadn’t called the police. Litchfield police picked up Luke and took him to jail for his actions. He was released the same evening after Lorelai paid his bail. The odd run-in was never mentioned again. 

Emily Gilmore was also arrested 

While it was shocking to see Rory Gilmore walk out of a jail cell, it was even more surprising to see Emily Gilmore do the same just a couple of seasons later. The Gilmore family matriarch was arrested for drunk driving in season 7 of Gilmore Girls

Richard and Emily Gilmore stand together at a Yale football game in 'Gilmore Girls'
Richard and Emily Gilmore | Netflix/Gilmore Girls
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Originally pulled over for talking on a cell phone while operating her vehicle, Emily was asked to take a breathalyzer test. She haughtily refused and was taken to the police station. She had to be picked up by Lorelai Gilmore later the same evening. Her run-in with the law was mentioned sparingly afterward. Still, fans of the series never learned if she was convicted of anything.