dissecting a divisive character: dean forester
ever since i properly watched gilmore girls for the first time in 2023, i’ve been plagued with opinions on it i’m unable to share with anyone in my proximity. taking them online meant realizing some of them were rather unpopular — especially my take on dean forester, historically a divisive character in the gilmore girls fandom. for me, he was a character that seemed to underscore a lot of the issues i had with the show and its consistently poor writing.
dean was approximately 16 when he was first introduced, around rory’s age. we’re not told much about who he was before he met rory but from his time on the show, we can safely assume he’s a typical teenage boy — in stark contrast to rory, who is absolutely not the typical high school girl. not only is she incredibly smart for her age. she comes from wealth, regardless of whether or not she’d like to shed herself of it. rory places quite a distance between herself and her privilege… at least until it directly benefits her, such her admission to chilton or her being able to attend yale.
dean, however, perfectly represents the working class of stars hollow. while rory spends her time out of school with her nose in a book, dean works long hours at doose’s market, a minimum wage rite of passage for the average teenager looking to make some money. gilmore girls is certainly not the right show if you’re seeking commentary and insight into the class divide. on the other hand, the dialogue raises questions surrounding the wealth and privilege of the titular gilmore girls. lorelai constantly mentions how hard she worked to get everything she has in life. she’s said to have worked her way to the role of executive manager at the independence inn but we don’t get to bear witness to this “work” the show keeps referencing. rory’s chilton education funding came from lorelai’s parents (in exchange for the gilmore girls joining lorelai’s parents for dinner once a week). 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’s generosity) came to save the day. so, one can only assume that her previous struggles were similarly bought off by her wealthy parents and her friends who are always more than willing to come to her aid.
the same cannot be said for dean. from the very first season, we see dean working at a grocery store, under an insufferable manager — a very realistic environment that most of us watching the show can probably relate to. unlike rory, he doesn’t plan to go to an ivy league school. aside from his lack of interest in it, he most likely cannot afford to. after his (very early) marriage, he doesn’t pursue higher education at all. as the sole provider in his relationship with lindsay, dean worked 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, dean and rory’s attempt to rekindle their old relationship reminds us of their socioeconomic incongruence. a paradigmatic example of this is rory’s awkward attitude about having a date in the break room at doose’s market because dean cannot seem to find spare time between his shifts.
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 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 responding in like to his love confession, the whole town threw him to the wolves. i can’t in good conscious blame rory for feeling overwhelmed by his confession; 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 lie and 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. on top of being ridiculously attractive, he was also the mysterious bad-boy type who puts all the other love interests to shame. i’ll admit to jess’s compatibility with rory and the well-written complexities of his character. but i’m also inclined to be believe that it was 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 love he and rory once shared. 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 every reason to be jealous. remember that before dean and rory eventually reached their tumultuous breaking point, jess wedged himself between the two at any given opportunity. in the picnic basket episode, he bought rory’s basket knowing she was intending to share it with dean. perhaps he just really liked her, but he also liked the thought of upsetting dean. at one point in the beginning of jess’s character, he (jess) and an unnamed boy from the high school got into a fight which dean tried to break up. when dean got in between the two boys, jess took his chance to swing a fist at dean. dean didn’t retaliate, of course — but wouldn’t knowing your girlfriend’s new friend hates you for no reason unsettle you in the slightest? jess is a trouble maker, we all know that. but dean never hated jess until jess began to overstep his boundaries, both with dean and rory. it was all too predictable when rory eventually cheated on dean with jess and suddenly, dean’s jealousy fell into place. did he handle it well? not at all. did he handle it the way a teenage boy would? precisely.
i’d 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 dropping out of yale or participating with dean in his infidelity. but none of this 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 mother, rory’s life is more or less the same as it was before the deplorable act. in fact, when confronted by lindsay and her mother, the show portrayed lindsay’s mother as a crazy woman driven by rage, trying to humiliate an innocent rory, standing silently beside lorelai, while lorelai finds the whole thing incredulous.
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 judgement for what rory chose to do of her own volition. and though 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 mistakes, there is always someone to blame more than her, seemingly a result of railing to kill your darlings. the creator of the show just loves rory too much.
now, i’ll never go as far as to justify dean’s behaviour when he cheated on lindsay. but here we are talking about a deeply flawed relationship from its inception and i think it’s worth exploring. dean’s arrangement with lindsay felt off from the moment it was announced. he was much too young to be married, barely having graduated high school. but it goes back to the desire he expressed in the earlier seasons about wanting a traditional life. lindsay seemed to provide it. we don’t know much about lindsay besides what dean says about her and we’ve already established that he is not the most reliable narrator. 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 a mother allows her daughter, who has just graduated 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 cook perfect dinners for her husband. dean’s parents don’t seem to be involved at all in the whole arrangement while lindsay’s mother is, to an almost suspicious degree. now none of this justifies dean’s treatment of lindsay but i do believe that some external pressures played a factor in the destruction of dean’s marriage. pensive whisker’s video essay called “dissected 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’m 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 forester is that he seems to be the only character in the entire show who truly has to 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.
