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Chuck Bass is definitely an interesting character. I really like his character development over the second season; him falling in love with Blair really turned things around. I also love the idea that him and Blair "could never work" because it's just a game to them. Both of them have urged the other to say "I love you" many times, but they just seem to never find the right opportunity.
Chuck had made a deal with Blair that he'd sleep with her if she said it, which I found rather symbolic. Even though Blair hadn't told Chuck himself yet, she told Emma, she girl she babysat, that sex was meant to be with someone you love. Blair and Chuck always treated their relationship as a game because apparently, "they'd be nothing without it."
The impact of lust on his life is genuinely insane but to be fair, Bart was exactly like that. Chuck has ruined a lot of his life because of the pleasure he gets from partying and sex. I can think of two examples: one where he leaves Blair waiting in Europe while he sleeps with another girl and two, when he goes out partying the day before his late father's business would go into his hands. His desires not only ruined his romantic life but his professional life as well.
Chucks character improved way more after Bart married Lily. He treated Eric like his actual little brother. In fact, something Eric said really stood out to me. When Georgina outed Eric at their family dinner, he reveals to Serena that Chuck was one of the few people he first came out to. He said, "He wouldn't judge me," and I suppose that's because of the many, many questionable things he has done and still does.
When Serena was confessing the truth about Pete Fairman, she talked about how she thought her friends would judge her. I found this funny, because one of Chucks reasonings as to why he wouldn't was, "I'm Chuck Bass." It does add up since he has the reputation of being quite the "womanizer."
One other thing that I found quite interesting is that after Barts death, he didn't want Lily as family because "he doesn't have a family." He did end up letting Lily adopt him, and maybe it was just so Jack wouldn't be his guardian, but I like to believe otherwise. He also punched Jack when he tried groping Lily at the opera, which definitely is not just because he hates Jack. He sees Lily as family, even if he doesn't always show it.
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I know I'm about a decade late to be writing about Gossip Girl, but I can't help it. I just started watching it, and I just have to do a character analysis based on what I've watched so far.
P. S. I've only watched until S2 E18
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