‘Gilmore Girls’: Is Rory Gilmore a Serial Cheater?

Rory Gilmore was presented as an all-around good girl. She did well in school, was said to be honest to a fault, and didn’t engage in any rebellious behavior in her teen years. In fact, her mother, Lorelai Gilmore, insisted she was the perfect kid. Rory may have been smart, but she wasn’t exactly as honest as Lorelai often claimed. In fact, Rory cheated on almost everyone she ever dated, form her very first relationship to the relationship fans were introduced to in the Netflix revival of the series.

Rory cheated on Dean with Jess

Rory’s flirtation with Jess Mariano wouldn’t have been a huge deal if she hadn’t been so transparent about it in front of her then-boyfriend, Dean Forrester. Flirting may not be cheating, but it eventually turns into that. Not only did Jess and Rory kiss while she’s still with Dean, but the pair spent several weeks trying to make each other jealous while they are with other people.

When they finally got together, thanks to Dean breaking up with Rory in front of the entire town, she still couldn’t seem to understand why Dean was upset. Eventually, Rory admitted that she still had feelings for Dean. Instead of just letting those feelings lie, she ended up sleeping with Dean while he is still married to Lindsay.

Rory cheated on Logan with Jess, too

Rory was pretty persistent in her pursuit of Logan Huntzberger, and when they finally get their relationship figured out, she seems happy, at least momentarily. She later finds out that, during a break, Logan slept with several members of his sister’s bridal party. While Rory claimed she forgave him, she most assuredly did not.

Rory headed down to Philadelphia to meet up with Jess, and the pair kiss. Some fans insist that her brief encounter with Jess wasn’t cheating, but she traveled out of state with the expressed intent to hook up with him. If that’s not cheating, what is?

Rory cheated on Paul with Logan  

When fans remeet Rory, she is in a relationship with Paul. The two had apparently been seeing each other for two entire years. It’s unclear how they ever got together in the first place, but Rory clearly wasn’t into him. That didn’t stop her from stringing him along, though. While in a relationship with Paul, Rory regularly met up with Logan for a little bit of romance.

The duo was sleeping together for almost the entirety of A Year in the Life while both of them were in relationships. Logan, engaged to Odette, doesn’t seem to mind the setup. Rory doesn’t seem to troubled by it either. There are a couple of people who may have had an issue with the random hookups, though. One can assume that both Paul and Odette would have taken issue with it.