Poll
‘Gilmore Girls’: Who Is Rory’s Best Boyfriend? (POLL)
Our annual fall rewatch of Gilmore Girls is about to hit completely different because October marks the show’s 25th anniversary.
While there was only one man who fans hoped to see Lorelai Gilmore (Lauren Graham) with at the end of Gilmore Girls (Seriously, was anyone actually Team Christopher?), her daughter Rory (Alexis Bledel) had not one but three worthy love interests, sparking one of the greatest debates in TV romance history: Who is Rory’s best boyfriend?
First, we have Dean (Jared Padalecki), Rory’s OG boyfriend, who stuck around during Seasons 1 and 2 and returned for the dark days, a.k.a. his and Rory’s “My Dean” affair during Seasons 4 and 5. While we don’t applaud the adultery, there is something to be said for first loves, even if they are meant to end. As Rory tells Dean during Gilmore Girls: A Year in the Life, “You were the greatest boyfriend alive… While I wish we would have met when I was older and more mature, I know that if I hadn’t had you with me when I did, I wouldn’t be the person I am today.” Thanks to Dean, we’ll never look at cornstarch the same way.
Rory’s second boyfriend, Jess (Milo Ventimiglia), came into the picture during Season 2, when he moved in with his uncle, Luke (Scott Patterson). While Jess was the bad boy to Rory’s bookish rule follower, the two found that they had a lot in common, ultimately both becoming writers during A Year in the Life. Many believe that Chilton Rory was too good for Jess during their early seasons together, and Jess became too good for Yale Rory when he returned in Season 6. However, it’s clear during every stage that Jess understands her like no other. After all, who else would know Rory well enough to hit her with the iconic gut-punch of a line, “Why did you drop out of Yale?”
While Rory’s Dean/Jess love triangle ruled her Stars Hollow days, Logan (Matt Czuchry) entered the scene once she hit Yale. Coming off a tad rich and arrogant, Logan represented the life that Rory would have had if she had grown up with her elite grandparents in her life. Introducing Rory to the Life and Death Brigade, Logan showed Rory how to take the leap (pun intended) out of her comfort zone. During A Year in the Life, it is revealed that Rory and Logan are still together-ish, hooking up even though he is engaged to another woman. Again with the adultery, Rory?!
With three major love interests to choose from, all with their own merits and drawbacks, it’s clear why fans are still debating who Rory’s best boyfriend was over two decades later. Vote below to settle Gilmore Girls‘ greatest debate once and for all, and be sure to sound off in the comment section about your favorite!
Gilmore Girls, Streaming Now, All Seasons, Netflix
Gilmore Girls: A Year in the Life, Streaming Now, Netflix
