When fans discuss Gilmore Girls, Rory’s dating history on the show usually comes up. Oftentimes, fans debate which boyfriend of Rory’s was better (or worse) and compare Dean, Jess, and Logan. While fans have discussed the faults of Rory’s boyfriends at length, what about Rory?
A look at Rory and Dean’s relationship in ‘Gilmore Girls’
Out of her three main love interests, Rory definitely treats Dean the worst. Part of this could be attributed to age, as Dean is Rory’s first boyfriend and she meets him when she is a sophomore in high school. It is also worth noting that most Gilmore Girls fans agree that Dean is Rory’s worst boyfriend.
From the start, it is pretty clear that Dean is more into Rory than she is him. When she is unable to say “I love you” after a few months of dating, he yells at her and breaks up with her. The two get back together at the end of Season 1 of Gilmore Girls, but in Season 2 Rory meets Jess.
Drawn to Jess, Rory and Dean begin to drift apart, which causes Dean to try and cling to Rory more. Even when Rory kisses Jess at the end of Season 2, she does not break up with Dean.
RELATED: ‘Gilmore Girls’: Who Was Really To Blame For Rory and Dean’s Affair?
“She doesn’t break up with Dean when she’s no longer into the relationship. She kisses Jess while with Dean, never tells Dean about it, and doesn’t break up with him after it happens even though she should. She’s not honest with her feelings in this relationship and even though it could be chalked up to inexperience, it’s still really unfair to Dean,” one Reddit user wrote.
After their breakup in Season 2, Rory and Dean reconnect in Season 4 when Dean is married. The two have an affair and Dean cheats on his wife, Lindsay. In this situation, both Dean and Rory are in the wrong.
Rory and Jess are fan-favorites
In Season 2 of Gilmore Girls, Rory’s feelings for Jess become too big to ignore and Dean breaks up with her. She starts dating Jess, and unfortunately, their mutual pining does not become a healthy relationship.
Communication wise, Jess is easily the worst of Rory’s boyfriends, and most of Jess’ shining moments occur long after he and Rory break up. As soon as they begin dating, he stops making as much of an effort in the relationship. Meanwhile, Rory begins to hang out with Dean without telling Jess, and she expects Jess to act the same way Dean did.
“I still think Rory unintentionally hurts Jess by comparing him to Dean and expecting him to act and treat her like Dean did. I also think she jumps to conclusions about Jess a lot, which hurts him because it shows mistrust… I just think there are things Rory does in this relationship that sort of lead into the reasons why Jess doesn’t open up to her (not that it’s an excuse, if he felt that way he should’ve ended things properly tbh) and has a tendency to shut down with her,” wrote one Reddit user.
Intentional or not, Rory gave Dean the benefit of the doubt over Jess multiple times, leading to mistrust and even more communication issues between her and Jess. Of course, Jess’ communication skills are so bad that he leaves Stars Hollow without officially breaking up with Rory.
Logan is Rory’s healthiest relationship in ‘Gilmore Girls’
Out of her main three love interests, Logan is the best at communicating, has similar interests, is intelligent, and he and Rory evolve together. However, the two still have their troubles, especially when it comes to communication.
In Season 6 of Gilmore Girls, Logan and Rory have a fight and stop speaking. Logan views the fight and silence as a breakup, while Rory does not. During this time, Logan sleeps with multiple of his sister’s friends. When Rory finds this out after they get back together, she is hurt and views this as cheating. Rory then seeks out Jess in an effort to cheat on Logan and the two kiss.
“Like, just because what Logan did was worse doesn’t mean Rory a free pass to go and kiss another man, no matter how guilty she may have felt about it after the fact or how quickly she ended it,” wrote a Reddit user.
Later on in the revival Gilmore Girls: A Year in the Life, Rory cheats on her boyfriend Paul multiple times with Logan while he cheats on his fiancée Odette. The bottom line is, no one in Gilmore Girls is perfect, not even Rory. Like any person, she has her flaws, especially when it comes to her relationships with flawed people.
Source: Read Full Article