While Gilmore Girls and Gossip Girl are both young adult dramas, that’s where the similarities end. Rory and Lorelai live in quirky Stars Hollow whereas Serena and Blair’s Upper East Side world is full of wealth and privilege. There’s one thing that both series have in common, though, and that’s a less than perfect romance.
Rory and Logan’s relationship has many ups and downs and he doesn’t seem to be an ideal boyfriend for her, and Chuck steals Blair’s heart early on in the series, then stomps on quite a lot. Blair could be immature but she definitely deserved better than the treatment she received from Chuck. While these love stories ended differently, as Chuck and Blair got married and Rory and Logan had a secret affair, it’s interesting to pit Chuck and Logan against each other.
10 Logan: He Cheated On Rory Thinking They Were On A Break
Rory thought that she and Logan were taking a break and that of course they would come back to each other. Logan must have thought differently because he slept with a few women during this time apart.
This was awful for Rory to experience, especially since she believed in Logan and felt that he had so much potential. This makes Logan a worse boyfriend than Chuck because while Chuck did treat Blair horribly at times, he was head-over-heels for her whenever they were officially together.
9 Chuck: He Didn’t Want To Be With Blair After Bart’s Death
Chuck’s father Bart died in the second season of Gossip Girl, or at least that’s what everyone thought happened. It turned out that he had faked his passing.
Chuck didn’t know that, though, and he was in mourning. Blair wanted to be there for him and Chuck wasn’t interested. He bailed on her and went to Thailand, and she felt horrible. This made Chuck a worse boyfriend than Logan, because when Logan faced hard times, he behaved immaturely, but he didn’t made Rory feel like he wanted nothing to do with her.
8 Logan: He Didn’t Have Any Idea About The Future
When comparing Chuck and Logan, it definitely seems like Chuck had a better idea of how to be successful. He might have gone about things the wrong way, since he loved scheming and manipulating others, but he wanted to secure a bright future for himself. He had a built-in work ethic from being neglected by his father for so many years.
Logan, on the other hand, didn’t seem to have much of a plan for himself. He had no goals and unlike Rory, who dreamed of being a journalist and traveling the world, he had everything handed to him so he never thought much about what would come next.
7 Chuck: He Loved Playing Games
In the third season, Chuck and Blair pretended to like other people so they could make each other jealous. It was all part of a game they were playing, but it definitely seemed toxic.
Chuck loved playing games with Blair, which makes him a much worse boyfriend than Logan, who would never do that. From the moment it was clear that they liked each other, Logan was kind to Rory and treated her with respect, even though they did have some problems in their relationship. Chuck never seemed to take Blair’s love for him seriously.
6 Logan: He Showered Rory With Expensive Gifts, But Was Emotionally Immature
While Logan could say the right things, he seemed more interested in showering Rory with grand gestures and pricey gifts instead of actually talking about his feelings.
From a coffee cart (and barista) to a confusing gift of a rocket, Logan was always giving Rory a present, and while she seemed to love it, was that really healthy? Logan didn’t like to talk about his life or his emotions, and Rory deserved a partner who could open up more and have adult conversations.
5 Chuck: He Set Blair Up To Sleep With His Uncle
In the third season episode “Inglourious Bassterds,” Chuck wanted to own a hotel, and his Uncle Jack said that would be possible as long as he could sleep with Blair. This was a shocking moment to watch, and all these years later, it still doesn’t make much sense.
Of course, Blair was mad, but how could she possibly love Chuck after finding out what he did? This was a terrible and disturbing thing to do, and it’s much worse than any mistake that Logan made in his relationship with Rory.
4 Logan: He Was Engaged But Had An Affair With Rory
When fans saw Rory and Logan again in the Netflix revival A Year In The Life, Rory and Logan had an affair.
Rory was in a relationship with Paul, and Logan was engaged to Odette. While neither was in a happy situation so they felt that they were justified, this was a big mistake on Logan’s part. He should have broken up with his fiance and confessed his love to Rory, if that’s really how he felt, or left them both so he could be work on himself. Logan was often selfish and he didn’t think about the consequences of his actions, which made him a less than ideal boyfriend.
3 Chuck: He Hated When Blair Dated Other People But Wouldn’t Admit He Loved Her
While there are many reasons why fans ship Blair and Chuck, there’s no denying that he could have been much kinder to her throughout the show’s six seasons.
In season two, Chuck hated that Blair was dating Marcus, but he wouldn’t take a risk and say that he wanted to date her. He even acted like he was having trouble sleeping with other women because he was still thinking about her, which was creepy for Blair to hear about.
2 Logan: He Proposed When Rory Wasn’t Ready For Marriage
If Logan had considered his proposal to Rory more carefully, it seems like he would have realized that Rory wasn’t ready for marriage. She loved him, but she wanted to travel and work hard and set up her life. She wasn’t interested in settling down.
Logan didn’t seem to understand Rory or take her feelings into account. It was immature to act like if she didn’t marry him, they would have to break up, as he made this big decision about their future and Rory felt left out of the planning.
1 Chuck: He Vowed To Ruin Blair’s Life
It’s not exactly healthy behavior for someone to declare “war” on their ex-partner because they said they didn’t want to date them, but that’s what Chuck did at the beginning of season four of Gossip Girl. Blair had many other love interests but she kept going back to Chuck despite how awful he was.
Feeling rejected, Chuck said it was war and that he would ruin Blair’s life. He wanted to mess up her chances of being a businesswoman’s assistant and he didn’t care much he hurt her. This is abusive behavior and not something that Blair should have forgiven Chuck for.
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