As fall is approaching, we’re confronted with old routines. We start to gravitate towards what’s comfortable; like hot drinks, bowls of soup and fuzzy blankets. This also spans to TV shows and movies. For some of us, this means an annual rewatching of Gilmore Girls. In honor of fall’s nearing arrival, we’re going to break down our favorite comfort show by psychoanalyzing the complex relationships of iconic characters!

It would be unnatural to start with anyone but our favorite mother-daughter duo! Although their relationship is problematic, and some may say unhealthy, we’re in agreement that Lorelai carries too much blame for Rory’s lack of morals, empathy, and overall likeability in later seasons. We think her trying to raise Rory as her friend instead of her daughter is very strange, and definitely contributed to her immaturity after she left for college, but we think Rory is coddled by all of Stars Hollow. They taught her she could do no wrong her entire childhood. Before Yale, Rory had never been confronted with discipline or realistic behavioral expectations. This isn’t just her mother’s doing, this is everyone’s: her grandparents’, her town’s and her boyfriends’. Admittedly, she’s gone through a few breakups and faced some adversity due to her mother’s financial situation, but that is really it. Not to mention that the financial difficulties she faced were all caused by her mother’s pridefulness.

Dean is arguably the worst of Rory’s boyfriends. Right off the bat, his character is unsettling as he stalked her when he was trying to win her over. At the beginning of their relationship, he was somewhat of a decent first love for Rory as he was kind to her family, makes her thoughtful gifts, and is attentive. However, this quickly digresses as his intellect and emotional maturity are not on par with Rory’s, often leaving him insecure. Dean was always very dismissive of Rory’s interests and selfishly never made an effort to do things she found engaging.

Another perturbing factor is Lorelai’s weird and almost obsessive fixation on him being the perfect man for Rory, which also seeks to exemplify one of the more unhealthy parts of their mother-daughter relationship. Lorelai constantly idolizes Dean, convincing Rory he is a ‘once in a lifetime’ opportunity when in reality he exemplifies a plethora of toxic characteristics. Additionally, whenever any other guy showed interest in Rory, Dean immediately grew unhealthily possessive and harbored animosity towards her despite it being out of her control. He eventually becomes really controlling of Rory and just all-around jealous. DON’T EVEN GET ME STARTED ON THE DONNA REED EPISODE. Possibly one of his most disgusting characteristics is his constant, underlying misogyny. It feels like Dean has this idea of a housewife being the pinnacle of success, like a trophy he has to work his whole life for. It’s very clear he sees Rory in this position from the moment he meets her.

Fans seem to love Jess, but he’s so annoying. He’s also only there for like two seasons so we don’t know why people care about him so much. The only thing we like about him is the fact that he breaks up Rory and Dean on their second round of dating. He’s pretentious, he’s rude and he’s absent in his relationship with Rory. Like the boy just up and runs away to Los Angeles days before her graduation without a word! However, Jess’ redemption arc begins in season 4 when he returns as a published writer. His maturity has grown exceedingly since the last time we saw his character and he can appreciate and see Rory’s good qualities. After he observes Rory’s life gone astray, he calls her out for not being true to herself. We feel like this is the turning point that Rory needs to wake up to her current failures and get back on track.

We have differing opinions on Logan Huntzburger. Some would say that he embodies everything Rory has grown into. Do we think he’s cocky, pretentious and an all-around stinky human? Yes. Do we think Rory is very similar? Yes. We think that those bad traits were Rory’s first impression of him and she refuses to admit that she’s just as bad as he is and that’s why she doesn’t marry him. The portion of the show that he’s in is very interesting to us.  It’s weird watching him better himself for Rory while she leans more into the “trust-fund baby, old money, sickeningly privileged” lifestyle. Logan goes from being a commitment-phobe who just wants a casual relationship with her to calling her his girlfriend to proposing to her in three years. We know this is the bare minimum, but it shows an immense amount of growth on his end.

Others would say, Logan’s the ultimate depiction of the toxic relationships we grapple with in our youth when we don’t have the skills to identify that his character is the epitome of a “red flag.” To start, Logan’s nickname for Rory, “Ace” is often perceived as a compliment to his charm and flirtatious beginning to his and Rory’s situationship. However, we find it to be patronizing to Rory as he almost exemplifies a position of power over her by belittling her like a child through his use of her nickname. His continual condescending tone towards Rory reveals the fragility of his ego as he often appears threatened by Rory’s intellect. We attribute Rory’s downfall to this man as he drags her into desiring a vain life of wealth and privilege despite it not being representative of who she is. Yes, Rory is responsible for her own actions, but they are indicative of her feelings of inadequacy in their relationship. 

Some could argue Logan pushed Rory to be more free and adventurous, but he really just crosses her boundaries and consistently pressures her in situations in which she feels uncomfortable. The more time she spends with Logan, the more her life deteriorates. Eventually, she turns into a person unrecognizable from the once sweet and ambitious Rory the show sold us on. She is not herself in their relationship. She drops out of Yale, moves in with her grandparents, steals a boat and is roped into a partying lifestyle. Additionally, Rory’s direct attempts to set boundaries in her relationship with Logan were often met with immature outbursts in which he profusely gaslit her into feeling unreasonable and controlling for wanting a monogamous relationship. We will say Logan isn’t entirely at fault for his undesirable qualities as his family is extremely neglectful and dysfunctional, with many of their values rooted in wealth and reputation, but he must be held accountable.

Lane deserves better! Time and time again we see her thrown aside by Rory, her alleged “best friend.” As soon as Rory gets a boyfriend, it seems that Lane is kicked to the curb despite her consistent support for Rory. Lane’s upbringing in a very strict home repressed her identity for years, but as she gains more ground with independence, her edgy and musical personality is set free. We respect her so much for never changing who she is to be what her mother views as acceptable. She’s resilient!

Paris Geller is a relentless force throughout Rory’s educational career. She always slays…seriously. She is an iconic depiction of a strong and motivated woman. Her borderline insanity when it comes to academic achievement is very telling of school being the only controllable factor in her life. Yes, her envy of Rory and deep insecurities can be overpowering, but she loves her at the end of the day and she always serves!

Emily Gilmore is the definition of a girlboss, but not in a cute way. We think she’s an awful person who doesn’t know how to express feelings of love, resulting in a tumultuous relationship with her daughter and granddaughter. She’s too invested in her image and her money.

Luke is a constant in Lorelai and Rory’s life, always showing up for them. We feel that Lorelai is undeserving of him because she took advantage of the fact that he was in love with her and constantly made him fix things, run errands, and do housework for her. She led him on for years and years, pretending to be oblivious to the fact that he loved her, while floating through other relationships on display for him to see. This might be a controversial opinion, but in later seasons we grow to dislike Luke after he finds out he has a kid. He becomes insanely self-centered and a terrible partner for Lorelai. We know we shouldn’t expect better from a show filmed in the early-2000s, but we also couldn’t move past the fact that Luke told the girls soccer team he was sponsoring to not be as aggressive when they play. When the little girl on the soccer team countered his statement with the point that the boys soccer team plays like that, he said, “Boys will be boys.” This scene definitely built some resentment towards his character for us.

There is a lot to unpack about each and everyone of these characters. Despite some being problematic and others adored, they will forever be held close as pieces of nostalgia in our annual fall magic!