Summary

• Rory's infidelity in her relationships is a recurring theme throughout Gilmore Girls, but she never cheats on Jess, showing her deep love and respect for him.
• In Gilmore Girls, Rory always goes back to Jess because they share a strong emotional connection and love for each other.
• The reason Rory cheats with Logan instead of Jess in the revival could be that Jess is too mature to condone cheating, while Logan is more accepting of it.

Though Rory has three boyfriends throughout the run of Rory's boyfriends in Gilmore Girls.

Throughout the original story, each of Rory's boyfriends has positive traits that appeal to her. Dean is thoughtful, Jess is intellectually stimulating, and Logan is adventurous. In the Gilmore Girls revival, her boyfriend Paul has no personality, to the point that Rory forgets he even exists. Ultimately, even though she likes all her boyfriends, Rory loves one more than the rest, as shown by an easily overlooked detail from Gilmore Girls.

Rory Cheats On Every Boyfriend Except Jess

Throughout Gilmore Girls and A Year in the Life, Rory can't seem to remain faithful to her boyfriends. In the Gilmore Girls season 2 finale, she cheats on Dean at Sookie's wedding. When Logan goes to Costa Rica with the Life and Death Brigade, Rory kisses another man. Then, in the revival, she doesn't even her boyfriend exists, leading to her frequently having sex with someone else. However, even in their roughest moments, Rory never cheats on Jess, setting him apart from all of her other boyfriends.

All the same situations that lead to Rory cheating with other boyfriends exist in her relationship with Jess as well. Rory has negative experiences with Jess which could motivate her to cheat, and Dean is very clearly still in love with her, giving her someone to cheat with. However, Rory has too much love and respect for Jess to look for intimacy elsewhere. Instead, she chooses to express her emotions in other ways that won't hurt Jess.

Rory Can't Resist Going Back To Jess

One other important aspect of Rory's infidelity is the fact that she continually runs back to Jess. The first time Rory cheats, she has an emotional affair with Jess while dating Dean, leading to them kissing when he returns to Stars Hollow. After her fight with Logan in Gilmore Girls season 6, Rory goes back to Jess. It's no coincidence that Jess is the person to whom Rory always turns. They both share a deep love for each other, making it easy for Rory to have emotional and physical intimacy with him.

The most probable reason Rory cheats with Logan in the Gilmore Girls revival instead of Jess is that Jess is too mature to be okay with cheating. He gets upset when Rory involves him in cheating during Gilmore Girls season 6, telling her that he deserves better. On the other hand, Logan never has a problem with cheating on partners, making him the perfect option.