A Look At Rory Gilmore's Boyfriends | The Odyssey Online
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A Look At Rory Gilmore's Boyfriends

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A Look At Rory Gilmore's Boyfriends

This past Saturday, Stars Hollow was once more. From Lauren Graham and Alexis Bledel (who played infamous mother-daughter duo Lorelai and Rory, respectively) to Keiko Agena and Todd Lowe (who played rock star couple Lane and Zack, respectively). Actors who played parts big and small in the show convened at the Austin Television Festival this past Saturday to participate in a panel about the show "Gilmore Girls." There were many questions posed, such as, “Where would the residents be now?” And “Will there be a movie?” (we’re all waiting, Amy). But one that has long been debated also came up: “Who was Rory’s best boyfriend?” None of them were perfect. Far from it. But I also can’t say which one was better than the others. This calls for a deep analytical look into each relationship.

Dean: The First Love.

First season Dean was pretty gosh darn adorable. He immediately took notice of Rory and her weird bookish ways and decided she was the one for him. It was obviously puppy love: their nervous interactions, their hesitation, the baking soda theft. And who didn't absolutely want to shake Rory when she didn’t say “I love you” back? It was heartbreaking. But then again, the way Dean handled it was pretty immature. He just pouted, was angsty, and broke up with her. Not cool. But with an “I love you, you idiot,” they were immediately puppy-dog eyes for each other again.

They went through a lot of firsts together. I feel for Dean when Rory started having feelings for Jess. He was just trying to be a nice boyfriend, but Rory was completely over it. But fast-forward to the Lindsay years, and Dean becomes a complete d-bag. I’m sorry, but if you knew you still had feelings for Rory, YOU SHOULDN’T HAVE MARRIED SOMEONE ELSE. And I don’t care if it was her first time and it was super romantic, you should not have slept with her. Cheating is cheating, buddy.

But overall, you could really tell that he cared about Rory and just wanted to be with her. Sure, he yelled at her and blamed her for everything that went wrong in his life. And yeah, it was extremely awkward when they tried dating again after his divorce. But he cared.

Jess: The Sensitive Bad Boy.

At first introduction, Jess is the stereotypical bad boy out of water. He moves from New York to the strange small town of Stars Hollow and immediately hates everything and is filled with angst. But then he meets Rory, who piques his interest immediately.

Let’s all remember that Rory was still dating Dean at the time, and while Jess may have been interested in Rory, the way he went about trying to get her was definitely bordering on excessive. He was confrontational to Dean, he hid Rory’s bracelet, and, correct me if I’m wrong, he invaded her room on multiple occasions. I get that you were interested, but damn boy, you need to simmer down.

But he wasn’t just all leather jacket and attitude. He devoured books at the same level as, if not more than, Rory. Whenever they were together, you could tell that they had a connection on multiple levels. He truly looked out for her when it mattered most.

However, Jess ran away from his problems, and that ultimately led to their separation. His cocky, know-it-all attitude finally got the best of him, he didn’t pass his exams, and he couldn’t take Rory to prom. He was just was so misunderstood. He tried to deal with things by semi-trying to rape her at a party and leaving her without saying goodbye. THIS IS NOT HOW YOU DEAL WITH THINGS.

He did come back briefly when Rory was dealing with Logan/Lorelai/yacht problems. And he matured! He wrote a book! He made Rory realize that her life sucked! This is a Jess I can get behind.

Logan: The Lovable Douchebag.

Everyone loves to hate on Logan. He is, after all, an entitled rich party boy with a family of diamond-encrusted blonde vultures (except his sister, the only decent one.) But people tend to skip over all of the growth that he (and she) made in their relationship.

When we first get introduced to Logan, he’s the typical East Coast preppy snob, riding by on Daddy’s coattails. Rory is not interested, thank the Lord. But one fateful umbrella jump later, she is smitten. However, there is an “are we, should we” situation happening that eventually leaves Rory crying on the bathroom floor. Don’t worry, they almost hook up at her grandparents’ vow renewal, so it’s all good again.

Their relationship is pretty much a bunch of ups and downs. At times it’s really, really great and Logan is acting like a proper boyfriend and overall, like a human being. He helped her drop her guard and explore her adventurous side. Although dropping out of Yale and joining the DAR was not the best solution for Rory, he knew that he needed to support her when she felt no one else did (after all, it was his father who ruined everything). Yet, as soon as things got bad, he goes back to being petty and childish (Cliff diving in South America, my friends, is not how you solve problems).

At the end of the season, their relationship is at a high. Rory is about to graduate college, Logan is trying to make a name for himself, and it’s all smooth-sailing. But then he proposes. At her graduation party. In front of everyone. I’m sorry, but he’s known Rory for many years now? How could he think this is a good idea, putting her on the spot like that? And he would also know that Rory would want to work and travel first before settling down. Which goes to show that Logan still had some growing up left to do, so it’s good that he and Rory never ended up together.

So who was the best boyfriend? I think it was put best by Scott Patterson (who played Luke Danes) during the panel: “None of them are good enough. Maybe one day.” And as was also pointed out, each of them came into her life when she needed them. As for the long-term, they all still had a long way to go. So who’s the one man she needs now? Simple: Obama. It is through following his campaign that she would become a successful reporter and eventually lead her to cover stories in Iraq and Afghanistan, fulfilling her life's dream. Thanks, Obama.

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This article has not been reviewed by Odyssey HQ and solely reflects the ideas and opinions of the creator.
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