Analyzing Rory Gilmore’s Relationships A deep dive into Gilmore Girls Relationships and what they taught us

By Nicole Scotton Staff Writer

Throughout the CW’s hit series, Gilmore Girls, Rory Gilmore is notoriously known for her complicated and questionable relationships. This comedy-drama attracts teenage girls all over the world, leaving them looking up to the loveable mother-daughter duo Rory and Loralei Gilmore, despite the pair possessing toxic relationships with their partners throughout the duration of the show. The series taught myself and many other viewers a variety of key lessons in regards to romantic relationships during one’s youth. Within the series, Rory has serious relationships with three guys through her high school and college career, including Dean, Jess and Logan.

Rory’s first boyfriend is Dean Forester, a handsome tall boy that she met in school who has much in common with her. In the beginning, Dean seems to be the perfect first boyfriend for Rory. Dean appears to always treat Rory right and it is clear that he truly loves her which many fans adore about him. However, no relationship is perfect, and this one proved itself to essentially be far from it. Dean broke up with Rory for the first time on their anniversary, right after Rory did not respond when Dean told her that he loved her. This sets the message that if one person says “I love you” then the other must say it back. Rory’s relationship with Dean taught me that I should not feel pressured to say “I love you back” to somebody when I am not ready to, despite what is portrayed on this show. If that person breaks up with me for this reason then that just reveals that they were not perfect after all. Not feeling ready to take the step of reciprocating those words does not mean the relationship must come to an end, but it taught me that if that person makes you feel guilty for it or attempts to pressure you into saying it back then maybe it should come to an end after all. Love takes time and should never be rushed or forced. Ultimately, Rory and Dean find their way back to each other and give things another shot. Once again, things appear to be going well until Rory finds herself falling for a new boy in town: Jess Mariano.

Rory’s undeniable feelings for Jess breaks Dean and Rory up yet again, and she ends up going out with this new boy in Stars Hollow. Jess is your stereotypical “bad boy,” always skipping school, driving fast and getting into fights, which is the complete opposite of her previous boyfriend. Despite Rory and Jess sharing many superficial differences, in reality they withhold numerous common values and morals. Rory’s mother, Loralei, strongly disapproves of Jess during their rocky relationship after he and Rory got into a car accident with Jess behind the wheel. However, Rory always ignored her mother’s advice and followed her own heart despite the teens reputation. While it is important to follow your heart and to put yourself first, listening to others advice can also be very beneficial. Sometimes in relationships one can become so blinded to all of the toxicity in their partner that it is hard for them to even notice it. And although many fans strongly support their short-lived relationship, their bond proves itself nonetheless toxic. Jess ends up leaving Rory without a trace for a long peri- od of time, thus ending their relationship. This relationship taught me that when in a relationship, it is okay to develop feelings for another person and move on. However, I believe that if this happens, then you must break up with your current partner and not do what Rory did. Jess’ immaturity also plays a major role in the pair’s downfall. The teenager constantly skipped school and did not take responsibilities and life in general very seriously, which is far different from Rory. Jess also was a broken character who I feel Rory did not take the time to truly understand. Jess and Rory’s dynamic proved it to be essential to fully understand your partner. After a long period of time passes, Rory finds herself back into Dean’s embrace for a third time. However, there is a larger problem at hand this time, and that is his wife, Lindsay. Dean married Lindsay shortly after his and Rory’s relationship came to a halting stop. It becomes evident to viewers that Dean did not truly love Lindsay the way he loved Rory. Instead of executing the decency of calling off the marriage and pursuing Rory instead, the two see each other behind an unsuspecting Lindsay’s back. Dean even goes as far as to take Rory’s virginity while he was still married to Lindsay. Yikes. This era for Dean and Rory is certainly the most toxic in my opinion. This part of the show re-emphasised the im- portance of loyalty in relationships. If Dean truly did love Rory, he should have and would have ended things with Lindsay immediately. Failing to do so proves that Dean was simply unloyal and a bad person overall. The show taught me with this final appearance of Dean that it is okay to walk away from an old boyfriend, even if he was your first love. Rory felt emotionally connected to Dean and therefore was blinded to all of the wrong she and him were doing.

During college, Rory meets Logan Huntzberger, who is everything who she thought she did not want in a boyfriend– wealthy, a little stuck up and coming from a family of great influence and power. Rory does not want to fall for Logan at first, but her feelings eventually overtake her and the two begin dating. This in itself was a lesson for me as it taught me to be more open-minded about relationships. Somebody does not need to be exactly what you think you want in a person, it is beneficial to try new things and to take risks because you might surprise yourself. Although this relationship was my personal favorite out of all of her other ones, it still proved itself unhealthy multiple times. For example, Rory and Logan got into a considerable fight and did not talk for a while. Instead of talking to Rory, Logan went and got with many girls, essentially cheating on Rory. However, Logan thought the two had broken up at this point but never communicated it. This brought the realization that communication in a relationship is very important. Logan was Rory’s last serious committed relationship that we see in the series.

Each of Rory Gilmore’s relationships taught her fans countless lessons regarding the ups and downs of romantic relationships. Although nearly all of the characters’ relationships ultimately proved themselves destructive, this just goes to show that it may take many relationships throughout your life to find the perfect partner for you. It is important to not look back at toxic relationships and to not regret them entirely, but to instead take an optimistic approach and to reflect what has been learned from them.