Rory Gilmore Boyfriend Battle

As my time writing these blogs comes to a near end, I think it’s only right that I discuss my very big thoughts on the men who have ventured into Rory Gilmore’s life. In the first season of the show Rory gets into her first relationship with a Stars Hollow boy named Dean Forester. He is the stereotypical heartthrob that you would expect in an early 2000s drama, but that never worked on me. Dean moves to Stars Hollow and begins school at Stars Hollow High during the time where Rory is transferring to Chilton prep school. He sneaks up one day while she is moving stuff out of her locker and says something stupid to try and catch her interest. Over the next few episodes, he just seems to always be there…One afternoon after their own school days Rory stumbles into the market that Dean works at and they start chatting. He offers her a can of pop, because he is from Chicago and they say pop there instead of soda, obviously. She accepts and as she goes to grab the can he leans in and kisses her right in the middle of the grocery aisle. Surprised by this, and holding corn starch, she says “thank you,” and runs out of the store without purchasing the corn starch. Unfortunately her and Dean date for quite some time, break up, date again, and then finally we are rid of him.

The next one in the mix is Jess Mariano. Jess is Luke’s (diner owner) nephew, whom his mother sent from New York for Luke to knock some sense into him as he had been acting out at school. Now Jess is known as the “bad boy” when categorizing Rory’s boyfriends. He smokes the cigarettes, he wears the leather jacket and puts gel in his hair, big whoop Jess defender until I die. A few days after his move to Stars Hollow, Lorelai invites him and Luke over to their house to welcome Jess to the town and introduce him to Rory. Now this does not go well, Lorelai tries to bond with Jess and he does not appreciate that and then everyone’s fighting and dinner is cancelled. That’s unimportant though, when Jess meets Rory he notices her bookshelves. Unknowingly he steals “Howl and Other Poems” by Allen Ginsburg off of her shelf only to return it to her that evening with some notes in the margins. It is probably beneficial to note that all this tom foolery was happening when Rory was still with Dean but again, unimportant. Jess did some questionable things and at the end of the day he and Rory were not meant to be together but I will still defend. Fun fact Jess becomes a writer in the series as well.

Now third, and final (endgame in my head) Logan Huntzburger. Rory and Logan meet during her sophomore year of college, they stumble into one another in the dorm hallway as Logan and his friends are in search of another girl, instead they find Rory. They have more of a slow burn romance, Rory was back with Dean when they met so their relationship strictly starts by them working together on the paper. However Rory’s grandparents get wind of this and insist that they must be together. Very soon after this, Rory and Dean have their final break up and Rory and Logan get together. Logan is from a very wealthy family which makes Lorelai nervous and she wasn’t always here for this relationship but she comes around. They stay together until Rory graduates college and he proposes to her…spoiler she says no. This is a very sensitive topic for me and every single time I watch this scene I magically think it’s going to change and it’s going to be a big happy ending, no. 

I could talk on this subject for days but the gist is, Dean = bad. Jess = misunderstood. Logan = the only correct answer. There are so many small things that happen between these three relationships that make everything I say here make a lot more sense but for now you’ll have to trust my opinions.