‘Gilmore Girls’: Rory Gilmore’s Biggest Relationship Flaw Wasn’t Her Propensity to Cheat

Gilmore Girls fans have discussed the romantic life of Rory Gilmore for decades. Rory was indecisive and difficult with all of her partners, but many fans point out Rory’s propensity for cheating as her worst trait as a romantic partner. While cheating is problematic, it might not have been her biggest issue. Rory wasn’t a good partner for many reasons, but her biggest red flag might have been her sense of entitlement and possessiveness even after her relationships ended. 

Rory assumed all of her partners wouldn’t move on after her 

Rory’s breakups were always more dramatic than the actual romance. That was mostly her fault. She became incredibly possessive once the men in her life finally moved on, even if she pretty much forced the end of the relationship. 

Rory seemed confused when Lorelai Gilmore mentioned Dean Forrester would be moving on, even though she immediately hooked up with Jess Mariano following the breakup. Gilmore Girls fans can mostly forgive that. After all, Rory was still a teen when she and Dean broke up. She didn’t get better about it with age, though. Rory was the one who refused Logan Huntzberger’s marriage proposal. Still, she seemed confused when he ended their relationship and mostly moved on. 

Rory Gilmore seemed flummoxed when her boyfriends ended the relationships 

Rory never ended a relationship. She did, however, force the men in her life to end things. Dean was the one to call things off all three times that he and Rory broke up, but she pretty much forced two out of three of their breakups. The first time, she refused to say “I Love You,” leaving 16-year-old Dean feeling hurt. The second time they broke up, Rory made it so obvious that she wanted to be with Jess that Dean all but had to call it quits. Each time the relationship ended, Rory acted confused by Dean’s actions. 

When Logan opted to move on from Rory after she refused his proposal, she was perplexed. When Paul decided to break up with her via text message, she wasn’t hurt but certainly seemed confused that he ended things before she did. In short, Rory wasn’t great to any of her partners, especially toward the end of the relationship, yet she felt entitled to their love. It was certainly an odd character trait for someone who seemed well-rounded and emotionally intelligent.  

Rory felt entitled to the men she dated even after her relationship with them ended 

Rory Gilmore’s biggest romantic issue was the possessiveness she displayed long after her relationships ended. When Lorelai pointed out that Dean and Lindsay were married when he and Rory hooked up, Rory freaked out. She refused to acknowledge that she was wrong. Rory screamed that he was her boyfriend “first.” The notion that Dean somehow belonged to her because they dated before he met Lindsay was a troubling display. 

Later, when Logan angered Rory, she ran off to try to hook up with Jess. Once again, Rory assumed Jess still belonged to her, despite their long-dead relationship. As a full-fledged adult, she did the same. Rory appeared to believe she had ownership over Logan, despite his engagement to Odette because she, once again, dated him first.