As summer comes to an end and the “ber” months begin, the Gilmore Girls are defrosting. As we all know, Rory Gilmore has been through plenty of turbulent phases, from Chilton to Yale to getting together with her married ex-boyfriend. Her taste in men throughout the years has definitely well… changed. Although she was seen as loyal and innocent at Star’s Hollow High I think Yale, that unfortunate haircut, and her academic downfall really took it out of her. I mean she used to be so in love and loveable until she was forgetting to break up with men, and going after men who were in relationships.
- Teen Jess Mariano
Teen Jess has to be first on the podium. When Rory was falling apart, rather than telling her it was okay, Jess fought for her future. Importantly, he was not only a great boyfriend to Rory, but a wonderful friend. After Rory moved in with her grandparents, rather than shielding her from consequences, Jess showed his maturity in relationships by giving her a reality check about how stupid she was for dropping out of Yale. Although Jess was initially presented as some bad boy, I do believe this kept Rory on her toes — and in a way, in line. Loreali was right about the initial judging though, the smoking and drinking is not okay. From first glance, Jess was certainly not the best guy, however, he is smart, witty and quick-to-play when it comes to Rory’s comments. This is reasonably better compared to Dean, who was lost all the time. Jess, although an imperfect, complex character, he was perfect for Rory. He communicated well and called her out on things that went against his boundaries.
- Teen Dean Forester
As a teenager, Dean was a pretty decent boyfriend. I will admit, his opinions on Donna Reed were unfortunate, but overall he was a good boyfriend (taking into account he was just a teenager). First off, he built her a car, and a classic car at that. Dean was able to set their differences aside, by going to dances with her. For a boy who was very uncomfortable with those situations, showing up for Rory like that was amazing. Not many teenage boys would wear a suit with tails and gloves to escort a lady. Although Dean had been put through so much, he was nothing but kind and respectful to Rory and her mother. I will say, I didn’t appreciate that Rory felt the need to change for him and hide things from him in fear of fighting. It’s one thing to not like confrontation, but keeping secrets rather than communicating is just wrong. However, in the end, I am proud of them for reconciling as friends before she attended Yale as it was a mature thing to do — especially since they were a part of each other’s lives for so long.
- Adult Jess Mariano
As the ultimate Jess lover, obviously, adult Jess has to be high up on my podium. He grew up to be an amazingly smart and mature man that still cared for Rory so much. I appreciate that Rory went to Jess with her problems as she knew that he would understand her. I mean, Jess even said “I know you better than anyone.” Her later going to him proves that. Later, when Jess reappears, in the revival series Gilmore Girls: A Year in The Life, rather than being together, Rory and Jess were adults with mutual respect for one another. Rory was struggling in her life as a journalist and Jess was there for her to lean on. Even though lots of fans have mentioned the fact that they would love Rory and Jess to continue their relationship, Jess still considers Rory as “too good” for him, making it impossible for them to rekindle their love.
- College Logan Huntzberger
In college, Logan was a decent boyfriend. It’s often said that Logan is the boyfriend that Rory loved most. While he did bring out a good side to Rory,I have to say I didn’t appreciate some of the other qualities in Rory he brought out; she stole a boat when she was with him, and got arrested. I will never understand the hype around Logan because he truly did cause Rory to suffer. She went through numerous crises and Logan was no help whatsoever. I get that he is a businessman, but Rory was his partner and he should have been there for her.
- Post-College Paul
Paul, known only for his brief appearance, and often deemed the forgotten boyfriend of Rory Gilmore. Throughout the series, Rory would often mention the mental note of having to break up with Paul. This all happened while she was in an affair with Logan. Loreali made her opinions clear, and even called Rory out about her disloyal decisions. Honestly though there is nothing to say about Paul though due to him simply not being in the series very long. To put it into perspective, we don’t even know his last name.
- Post-College Logan Huntzberger
Tied for the last places are adults Logan and Dean. Maybe I’m just a hater,but I really do feel that Logan is awful. He was in a deeply-committed existing relationship when he reconnected with Rory — even if it was just with a fiance and not a wife, an affair like that is a major encroachment. The fact that he not only went out with Rory but ended up getting her pregnant is just not okay. He cheated. Then, he proceeded to ruin Rory’s life as well as his fiance’s.
- Adult Dean Forester
I can say with full confidence that Dean grew up to be a terrible man. After he and Rory broke up officially, Dean moved on to Lindsey. I strongly believe that if Rory had just backed off once she went to Yale, and not tried to be friends with Dean after their two year relationship, Lindsey would not have been cheated on. So in reality, this relationship soured because of both Dean and Rory. However, I will say I am proud of Rory for not going to the wedding and just standing by –especially after a drunk Dean confessed his love for her. Although Rory didn’t know about the drunk confession, the fact that she still went after a married man was upsetting. Again, Loreali made her opinions clear by emphasizing: “He’s not your Dean, he’s Lindsey’s Dean,” which only made Rory more upset and distraught, which was an ultimate point of embarrassment for her.
