“You’ve never seen Gilmore Girls?!” That was the incredulous reply from a friend last year when her Stars Hollow reference sailed over my head. Honestly, I avoided watching the show since it came out because I thought the fast-paced, witty banter I’d heard so much about was going to annoy the crap out of me. But at the end of 2022, with the urging of said friend, I decided to finally give in to the call of that cozy, small Connecticut town and its quirky inhabitants.
Despite my initial skepticism, I’ve become a passionate Gilmore Girls fan in my own right, indulging in the fantastical escapism and soapy storylines. Because despite showrunner Amy Sherman-Palladino’s opinion on the matter, a big part of what kept me, and many other fans watching, was the love lives of both Rory and Lorelai. Would Luke and Lorelai ever get together, or would something (or someone) always get in the way? And who would Rory ultimately choose: Dean, Jess, or Logan?
That last question seems to be one that many a fan continues to actively debate despite the ending of the show and the events of Gilmore Girls: A Year in the Life. While I was staunchly Team Dean from the beginning, I didn’t realize how polarizing that choice was. As I’ve delved deeper into the fandom, I’ve run into plenty of Team Logans and a fair share of Team Jesses. But Team Deans are few and far between.
Why don’t more people like Dean, though? The choice seemed like an obvious one to me. But clearly, there’s not a consensus among fans. So I decided to take one for the team and defend Rory’s first love (How very Dean of me). As a first-time watcher, I’m going all in for Team Dean and examining why he was the best of Rory’s boyfriends.
Dean’s Emotional Stability Set Him Apart
The relationships you have with other people and yourself play a major part in your romantic partnerships. And one of the things that stood out to me about Dean was his relationships. His relationships with his family, and himself, were much healthier than Jess’ or Logan’s. While I probably wouldn’t have noticed this had I originally watched Gilmore Girls as a teenager, as a thirty-something married woman, it definitely has weight now.
Dean has both parents in his life. And they’re still together and live under the same roof. He has stability at home unlike Jess who didn’t have his father around. And Logan who has a strained relationship with his parents. Dean is also close with his little sister, Clara. And you can tell she idolizes him. Because Dean has sisters, he’s also more in touch with his feelings and able to communicate them than say, Jess (who acts defensive or runs away), or even Logan (who parties away his feelings). Having a perfect relationship with your family is by no means a dealbreaker. But in this case, Dean’s allows him to be a better partner to Rory.
Dean’s emotional stability is a selling point because it allows Rory to feel safe enough to open up and explore her own feelings. When Dean and Rory first broke up, it was because Rory didn’t say “I love you” back right away. Rory didn’t know what to say in the moment because those feelings were new to her. She was emotionally immature. And in some ways, in denial about how she felt.
I’m a Rory stan for sure. But the girl definitely struggled with her insecurities throughout the show. Can you blame her, though? Lorelai wasn’t exactly a prime role model for healthy relationships. Rory witnessed all of Lorelai’s stops and starts with her beaus, especially Christopher. And she knew that even though Christopher and Lorelai loved each other, there was no commitment (at least initially) on Christopher’s end. That’s not exactly a reassuring example of the meaning of those three little words.
He Would Do Anything to Make Her Happy, Even Go to a Cheesy School Dance
Dean put Rory’s fears to rest by consistently showing her just how loving and committed he was. Even from the very beginning of their relationship, he was perfectly willing to hang out with Rory and her mom and watch old movies if that meant he could spend time with her. In fact, he was the only one of Rory’s boyfriends that Lorelai had a solid relationship with. Seeing as Lorelai and Rory were best friends as well as mother and daughter, Dean scored major brownie points in this area. Lorelai even went so far as to call him “the perfect boyfriend” at one point.
Despite his reluctance to do so sometimes, he was also always willing to compromise and do things for Rory just to make her happy. He found a date for Lane so that he and Rory could go on a double date together with her. He went to a Chilton school dance even though he, like many guys his age, would not want to be caught dead at one. And he even suffered through the dreaded Friday night dinners because it meant a lot to Rory that her grandparents meet him.
The fact that Dean makes an effort to not only be nice (unlike Jess) but actually have a relationship with the important people in Rory’s life shows emotional maturity. And just how much he cares for her and wants to be with her. He always put Rory first (even when she couldn’t always reciprocate). And managed to integrate into her life in Stars Hollow the most.
Dean Showed He Could Be a Good Provider
Dean was also always attentive to Rory’s needs and did everything that he could to give those things to her. Despite him not having as many resources as say, Logan (i.e. a trust fund and Daddy’s money). Going back to that three-month anniversary episode, Dean reveals he was building Rory a car. Not only is that incredibly thoughtful and generous, but it also shows that Dean is good with his hands if you know what I mean (hint hint, wink wink). All jokes aside, while Logan was a provider in the monetary sense of the word, Dean showed he was a provider in the practical sense of the word, much like Luke was for Lorelei.
Dean and Rory Had a Deep Emotional Connection
Although many anti-Dean fans like to harp on him for then becoming super clingy in Season 2, he acted that way because he and Rory were spending less time together. And he didn’t want to lose her. Dean also saw both Tristan and Jess as threats to what he had with Rory. He started calling her more and showing up at Chilton to make sure he was still top of mind. In the end, he was afraid that Rory might like one of them more than him. And as it turned out, that’s exactly what happened.
But even after they both seemed to move on, Dean and Rory’s emotional connection continued as they confided in and supported one another through life’s ups and downs. The stability of that connection, despite everything they were going through separately, ultimately laid the foundation for their sexual relationship to bloom. Rory felt safe enough with Dean—especially after Jess’ emotional volatility—to give him both her heart and her body. Although it would have obviously been better if they hadn’t hurt Lindsay in the process, they certainly weren’t the first people to have an affair or go back to their ex.
While they eventually realized they were on different trajectories and their lives no longer fit together, Rory and Dean continued to encourage and look out for each other. Making sure the other person never lost sight of who they were or what was truly important to them. For Rory that was Yale and her journalism career. And for Dean that was finishing college, getting married, and starting a family. They both just wanted each other to be happy. And in the end, isn’t that what love is?
While he may not have been as mysterious or adventurous as Jess or Logan, Dean was a dedicated and loving boyfriend to Rory. The emotional maturity that developed during their relationship was an important guidepost for Rory to compare her future relationships. And Dean’s kindness, dependability, and support made him an ideal partner. And at some point in her adult life, Rory realized this too.
First loves don’t usually last. But the impact they have on us is life-long. And in the words of Rory Gilmore, Dean was “…the greatest boyfriend alive…” and he “…taught me what safe feels like.”