It’s that time of year again where everyone is finishing their annual rewatch of Gilmore Girls, and that raises the controversial question of who is best for Rory Gilmore.

             Let’s start this comparison by going through Rory’s time with each of these boys. Rory (Alexis Bledel) met Dean (Jared Padalecki) on her last day of her conventional high school before leaving to private school. Dean is a generic first high school love. They dated for two years and on paper Dean was a great boyfriend with little red flags that raised some concern. Dean would say things like how he thinks it would be better to have a wife that stays home and cooks and cleans for her husband, Dean also shows a lot of signs of anger issues.

             Rory meets Jess (Milo Ventimiglia) after he moves to her small down with his moms hope of him getting on a better path in life. He is considered to be a bad boy with a soft spot for Rory. Dean ends up leaving Rory once he realizes her feeling towards Jess. Jess had a hard life, and he was not on track to graduate high school, him and Rory dated for a few months, and he wanted to be good for her but could never fully get his act together. After falling in love with Rory he left to go find his dad leaving Rory, so she decided to move on.

             Last there is Logan. Logan is a rich boy who Rory meets at Yale who teaches her to live life to the fullest. He was never considered to be a relationship guy and only liked casual flings, but that all changes when he gets to know Rory. Rory has a lot of problems with Logans family as they do not think she is good enough to uphold their family name. They date for the majority of Rory’s time at Yale. They were deeply in love but their lives were going in different ways which led Rory to reject his proposal.

             Now lets get into the comparison. Personally, I haven’t met anyone who is team Dean, with his anger issues, and an incident in season 5 where he cheats on his wife with Rory. It is mostly between Jess and Logan.

             Jess is a very good example of right person wrong time, as he was going through huge life adjustments and couldn’t fully get it together at that time. He loved Rory so much and would’ve done anything for her, and she eventually was an amazing influence on him. He knew he needed to leave and meet his dad so it didn’t work out, but would it if they had met later, or he didn’t leave?

             Logan (Matt Czuchry) and Rory’s relationship wasn’t always the healthiest but their love for each other won over every time. He changed for her and would’ve done anything to make Rory happy. When their lives started to go in different directions he didn’t want to end things so he proposed, but she wasn’t ready to give up on her career and her dreams so she turned him down.

             With all of these facts everyone has a different opinion on who is best for Rory but normally it isn’t Dean and if you ask me its for good reason. I find myself going between Jess and Logan all the time, but I always fall back on Jess.

             When Jess was in the picture the show was in its peak years, and I think Jess had a lot to do with that. His love and loyalty to Rory gives him the win from me. His character development in the 3 seasons he was involved was amazing and the majority of that was because of his love for Rory and his willingness to do whatever is best for her. Therefore the best boyfriend of Rory Gilmore is Jess Mariano.