Gilmore Girls: All 3 of Rory’s boyfriends ranked from worst to best

Rory Gilmore had three great loves in Gilmore Girls, but which boyfriend was the best and which was the worst? Let's rank Dean, Jess, and Logan.
1 of 4

If there's one aspect of Gilmore Girls that earns the most spirited debate among fans, it's the ranking of Rory Gilmore's three most important love interests. Across the seven regular seasons of the hit series, Rory had three boyfriends: Dean, Jess, and Logan. To quote Ariana Grande, one taught her love, one taught her patience, and one taught her pain. Can you guess who fits into each category?

Rory's first boyfriend --- her first love --- was Dean Forrester, played by Jared Padalecki. The teens meet in the pilot episode, and thus begins a years-long love affair (and I do mean "affair" in every sense of the word). In the midst of her relationship with Dean, Rory develops an attraction to Luke's bad-boy nephew Jess Mariano (Milo Ventimiglia), who arrives in town with a sour attitude and intimidating good looks. Listen, Jess had everyone shaking in their boots.

The Dean vs. Jess debacle was quite the doozy, but another man entered the ring when Rory went off to college at Yale. She started dating the mysterious trust-fund rebel Logan Huntzberger, brought to life with a swoon and a devilish grin by Matt Czuchry. To say Rory and Logan's relationship was tumultuous would be an understatement, especially considering the events of Gilmore Girls: A Year in the Life.

Each of Rory's boyfriends have their pros and each of them have their very obvious cons --- and we know how much Rory loves to make a pros and cons list. Allow me to make a version of Rory's classic pro/con list by diving into all three of Rory's Very Important Boyfriends and ranking them from worst to best. While the ranking might not be reinventing the wheel, we're going to get into the nitty gritty of Dean, Jess, and Logan and share some hot takes on the relationships. So, first up: Who's the worst?