Autumn means we’re all rewatching Gilmore Girls. Not me. This Autumn I picked up Gilmore Girls for the first time (I watched 5 episodes last year but got bored and dropped it). After that fifth episode, I felt myself going down the rabbit hole. I started to actually have opinions on the show and a lot of them. The one I want to share with you in this piece is all about Dean Forrester. Don’t sigh yet, just hear me out. Dean’s character was rough to watch but he also stood out to me in juxtaposition to the other characters in this series.
When Dean was first introduced, he was approximately 16, around Rory’s age. We don’t know much about who he was before he met and fell in love with Rory but, judging by who he is after, it seems like he’s your typical high school boy. This is a stark contrast to Rory who absolutely is not the typical high school girl. Not only is she incredibly smart for her age, she comes from wealth regardless of whether she’d like to shed herself of it. Rory likes to separate herself from her privilege… until it can benefit her (see: Chilton, Yale, etc.).
Dean, however, is the perfect depiction of the working class. While Rory spends her time away from school with her nose in a book, Dean works in Doose’s market, a rite of passage for teenagers looking to enter the working world. Gilmore Girls is not the kind of show to look for if you want commentary and insight into the class divide but simultaneously, the dialogue is thought-provoking when it comes to wealth and privilege. Lorelai constantly mentions how hard she worked to get everything she has in life but we don’t get to bear witness to all this hard work she keeps referencing. Rory’s Chilton education funding came from Lorelai’s parents as did her funding for Yale before Rory’s father coincidentally came into millions of dollars worth of money which would cover the rest of her tuition. When Lorelai was looking to open the DragonFly Inn and was worried about the cost of the repairs, her father’s investment money (and Luke) came to save the day. So, one can only assume that her previous struggles were similarly bribed or bought off by her wealthy parents.
The same cannot be said for Dean. From the very first season, we see Dean working at a grocery store with an insufferable manager (something most of the audience can relate to). He doesn’t have plans to go to an Ivy League. Along with showing little to no interest in it, he most likely cannot afford to. After his (very early) marriage, he didn’t pursue higher education at all. As the sole provider in his relationship with Lindsay, Dean was working two jobs and picked up every extra shift he could get in order to afford a nice townhouse for himself and his wife. Even after the divorce, when Dean and Rory attempt to rekindle their old relationship, it seems that they are too socioeconomically incongruent to stay together, epitomized by Rory’s awkward attitude at having to have a date in the breakroom at Doose’s Market because Dean cannot seem to find spare time.
Class divide aside, Dean was only a kid when he was first introduced. As I previously mentioned, Rory was smart for her age, often acting in loco parentis during Lorelai’s periods of irresponsibility. Her portrayal of the sweet, innocent child that every parent dreams of makes even her bratty moments seem cute and redeemable. On the other hand, Dean’s childishness and inconsideration get blown out of proportion. Next to Rory, all of the natural shortcomings of a teenage boy look hopelessly unforgivable.
In the Donna Reed episode, Dean showed desire for a traditional wife. Nothing about his opinion on the topic was surprising but rather than opening up a meaningful conversation about it, Rory and Lorelai proceed to ridicule him and housewives alike. When Dean felt upset at Rory for not saying ‘I love you’ back, the whole town threw him to the wolves. I don’t blame Rory for feeling overwhelmed by the statement, nobody should be pressured into saying those three words. But Dean’s response to that lack was equally understandable. He was a teenager whose moment of emotional vulnerability wasn’t reciprocated by the girl he loved. While Rory was emotionally mature enough in that moment to not say she loved him, Dean wasn’t, which is pretty realistic behaviour for a boy his age.
Jess’s introduction into the story further exacerbated all of Dean’s imperfections. Alongside being ridiculously attractive, he was also the mysterious bad-boy type who puts all the other love interests to shame. I am inclined to believe that it was at this point that the narrative began to go against Dean in every way possible. While I do acknowledge that Dean had his unpleasant moments, Jess’s introduction destroyed whatever was left of the sweet puppy love he and Rory once had. Suddenly, the thought of spending time with Rory seemed to exhaust him and his usual teenage jealousy was heightened to an appalling degree. But Dean had reason to be jealous. Before she cheated on Dean with Jess, Rory was most definitely making her way towards it little by little.
And this is where I would like to take a moment to discuss Rory. Rory Gilmore is the apple of the creator’s eye. She comes with infuriating moments of her own such as when she dropped out of Yale or when she participated with Dean in his act of infidelity. But none of these actions have impactful consequences. In a small town full of gossip mongers, Rory and Dean cheating on Lindsay should have made the both of them social pariahs. But other than a well-deserved scolding followed by a silent treatment from her mom, Rory’s life is more or less the same as it was before the deplorable act. The same can be said for the time she stole a boat with Logan and got herself arrested. Logan suffered the brunt of Lorelai’s chastisement and judgment for what Rory chose to do of her own volition. And although Rory was sentenced to several hours of community service, none of this affected her life in any meaningful way. For every one of Rory’s misjudgments, there is always someone to blame more than her and I think this is a result of failing to kill your darlings. The creator just loves Rory too much.
You’re probably wondering how I’m going to justify Dean cheating on Lindsey. I’m not. Personally, I believe cheating is an unforgivable sin. But here we are talking about a deeply flawed character and I think it’s worth exploring. Dean’s arrangement with Lindsey felt off from the moment he announced it. He was much too young to be married, barely having graduated from high school. But this relates to the desire he expressed in the earlier seasons about wanting a traditional life. Lindsey seemed to provide it. We don’t see or know much about Lindsey besides what Dean says about her and we’ve already established that he is not the most reliable of narrators. From what we do see, it seems as though Lindsay’s mother is heavily involved in the girl’s life, before and after the marriage.
What kind of mother allows her daughter, who is barely out of high school, to get married, to a boy she hasn’t dated for particularly long? Perhaps the kind that expects a traditional life for her daughter. After the marriage, Lindsay didn’t go to college nor try to get a job. She usually spent her time at home trying to make perfect dinners for her husband. Dean’s parents don’t seem to have been involved at all in the whole arrangement while Lindsay’s mother is, to an almost suspicious degree. Now none of this justifies Dean’s behaviour towards Lindsay but I do believe that some external pressures played a factor in the destruction of Dean’s marriage. Pensive Whiskers’ video essay called “Dissecting a Divisive Character on Gilmore Girls” delves deeper into Lindsay’s character and I encourage anyone interested in this aspect of the show to check it out on YouTube as well as her other brilliantly worded video essays about Gilmore Girls.
By no means do I think that Dean was a picture-perfect boyfriend. In fact, I am truly of the opinion that Dean and Rory were not compatible enough to make it past high school. What I find so interesting and kind of dark about the decline of Dean Forrester is that he is the only character in the entire show who seems to have to truly pay for his bad choices. While Dean has done some morally reprehensible things, his downfall just stayed with me even after his character was long gone.