Best Boyfriends – Gilmore Girls Edition

So I’ve decided to take the best boyfriends/girlfriends on some of my favorite shows. Mostly, I plan on it being an ensemble cast where I talk about the character they ended up with and whether that was a right decision or not. Hopefully it’ll play out better than it currently sounds. But with one of my favorite shows Gilmore Girls, it was hard to highlight the whole cast. There’s a lot of great characters and I feel like the majority end up with the people you thought all along. I was always most interested in the boyfriends of Rory Gilmore. She had three serious relationships with three very attractive males. The order I’ve listed them is just chronologically, but I will discuss which she should’ve ended up with.

Dean Forrester

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Dean was Rory’s first boyfriend on the show. He was the kid with nice hair who had just moved from Chicago to the school Rory left shortly after the series began. Dean watched Rory read day after day and they eventually ended up getting closer. They shared their first kiss in the market where he worked. Dean was a sweet character but he eventually annoyed me. He was loyal to Rory but they were extremely on and off throughout the series. Stuff always got in the way of their relationship, as it often does but this was serious unforgivable stuff. Not to mention, Rory lost her virginity to Dean while he was still married. I’d say by the time that went down on the show, it was obvious it was time for Dean to get lost. He was a character that should’ve only been around until season 3. That’s the storyline he should be remembered for, not the way he ended up which was as the guy that cheated on his wife with his ex girlfriend.

Jess Mariano

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Jess is definitely the one out of the three that I would’ve went for. The guy has great taste in books plus he can keep up with Rory’s constant pop culture references which isn’t an easy task. Sure, he’s a bad boy. But he’s the one of the bunch who ended up in a fairly stable position and Rory messed him over. He left her many times when he should’ve told her how he really felt. Rory ultimately needed a guy that would be there for her – which sadly, wasn’t in Jess’s nature. I think this was a beautiful relationship while it lasted and it’s one that Rory needed to experience. He broke her heart by bailing and she truly loved him.

Logan Huntzberger

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Logan is a character that annoyed me a lot in the beginning. However, I do think he really cared about Rory. He couldn’t help what family he belongs to, but he could’ve been more grateful. Instead he was a spoiled white boy who never really had to work at anything and we never really saw him work hard for anything while he was on the show. It was a rather safe choice for her since he came from a nice family and her grandparents worshiped him simply due to his last name. Logan really grew up as his relationship with Rory became more serious. It was wrong of him to blindside her by popping the question at her Yale graduation party her grandparents threw. All in all, he was a fun and different character that was a good match for Rory.

Who Rory ended up with: No one. At the end of the series, Rory turns down Logan’s proposal in order to focus on her career instead of moving away to be with him. It was a fitting decision for her, she was always meant to be a career woman first.

Who she should’ve ended up with: Well, Rory and Logan should’ve ended things long before the proposal. I think she should’ve chose Jess the second she went to visit his bookstore and saw how well he was doing. He had his life in order and Rory should’ve ended up with him somehow. I get why she didn’t end up with him but I still think he was the all around best of the boyfriends.

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