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Lorelai Gilmore and Rory Gilmore had no shortage of love interests. During Gilmore Girls, Lorelai had five significant romances, while her daughter dated three different men for a considerable amount of time. It might be an unpopular Gilmore Girls opinion, but both Lorelai and Rory were pretty terrible to the men in their lives.

Lorelai walked away from several men at the first sign of trouble

Lorelai Gilmore left no shortage of broken hearts in her wake. In season 1 of Gilmore Girls, Lorelai dated Max Medina, Rory’s English teacher. While Max was problematic in many ways, Lorelai was pretty cold to him, too. She even opted to end their engagement shortly before their wedding date. 

In season 4, Lorelai seriously dated Jason Stiles, her father’s business partner. Her intentions weren’t pure from the start, but eventually, she grew to like Jason. The relationship ended when Jason decided to sue Richard Gilmore. A lawsuit might be a good reason to end a relationship, but Lorelai never gave him a chance to explain the situation. Within weeks she had already moved on to Luke Danes. 

Lauren Graham as Lorelai GIlmore, Alexis Bledel as Rory Gilmore, and Scott Patterson as Luke Danes at Luke's Diner in 'Gilmore Girls' Luke and Lorelai's relationship is at the center of several 'Gilmore Girls' unpopular opinions
Lorelai Gilmore, Rory Gilmore, and Luke Danes | Saeed Adyani/Netflix

Gilmore Girls fans might have largely loved Luke and Lorelai together, but things weren’t perfect there either. Lorelai called off her engagement to Luke Danes, too. It might have been justified, but she slept with Christopher Hayden, Rory’s father, the same night and eventually married him. Christopher and Lorelai’s relationship ended when it was clear she was still into Luke. Both Christopher and Luke deserved better. That, in and of itself is an unpopular Gilmore Girls opinion, though.

Rory Gilmore cheated on both Dean and Logan 

Rory wasn’t nearly as calculated as her mother, but she still behaved poorly in most of her significant relationships. She cheated on her first boyfriend, Dean Forrester, with Jess Mariano when they shared a kiss. She went on to basically flaunt her interest in Jess in Dean’s face until he finally broke up with her. Long after Dean had moved on to his wife, Lindsay Lister, Rory remained in his life. Eventually, she started hooking up with Dean while he was still married. Rory wasn’t the only one to blame there. Still, she played a significant role in the demise of his marriage.

Jared Padalecki as Dean Forrester and Alexis Bledel as Rory Gilmore in Gilmore Girls: A Year in the Life
Dean Forester and Rory Gilmore in ‘Gilmore Girls: A Year in the Life’ | Neil Jacobs/Netflix

Rory had a significant interest in Logan Huntzberger, her college boyfriend, before her third attempt at a relationship with Dean ended, as well. Logan and Rory’s relationship wasn’t smooth sailing, though. During a break, Logan hooked up with multiple girls. Once Rory learned about it, she retaliated and cheated on him, too. This time, she headed down to Philadelphia with the intent to hook up with Jess to basically even the score.

Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in Gilmore Girls
Rory Gilmore and Logan Huntzberger | Saeed Adyani/Netflix
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‘Gilmore Girls’: Rory and Lorelai Gilmore Didn’t Really Casually Date and Neither Did Anyone in Stars Hollow

Rory was probably the most genuine and the nicest she has ever been to a partner when she was with Jess. Jess, however, wasn’t all that great to Rory. Eventually, he disappeared from Stars Hollow. Interestingly enough, Rory’s relationship with Jess was the shortest of her major romances. It might be an unpopular Gilmore Girls opinion, but it seems likely that she would have treated him poorly if he had given her the opportunity.