Chuck Bass was one of the most controversial figures in 2007's teen drama Gossip Girl. Starting out as a sexual predator, the audience was not quick to forgive him. Even when he found redemption in his relationship with Blair Waldorf, he still made mistakes.

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Chuck was always a work in progress. Some of his decisions stemmed closer to assault than anyone was comfortable with. Eventually, Chuck did redeem himself in the final two seasons of the show. He matured as a person and finally became someone that was able to function in a loving relationship. But even so, some things are just unforgivable.

Assaulting Women

Chuck’s initial introduction into the glamorous world of Gossip Girl was as a villain. Though he was Nate Archibald’s best friend, Chuck was also the antagonist for the first episode and many after.

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Chuck first tried to force himself on Serena after she came back from boarding school. Serena fought him off and he went on to fight another day. This, unfortunately, came at the expense of Jenny Humphrey who he attacked later in the episode. Despite the strides he made to make amends, this was a point of his character that was never forgotten.

Slut-shaming Blair

Blair Waldorf walking while looking sad in Gossip Girl

When it came to an eye for an eye, Chuck always had a sense of justice. He fell hard for Blair but when he got his heart broken, he was unforgiving. Blair slept with Chuck but ultimately went back to her ex-boyfriend Nate.

Chuck never had his heart broken before and took it out on her. He blogged to Gossip Girl that Blair had slept with two people in the same week. Blair’s reputation was destroyed. And when Nate found out that Blair had slept with Chuck as well, he broke up with her.

Blind Loyalty To His Father

Chuck and Bart talking

Chuck endured harsh treatment from his father. But until the very last season, Chuck remained loyal to him. Throughout his life, Bart led Chuck to believe that his mother had died in childbirth. Bart slung hurtful words at his son. And although Chuck’s actions were his own, the damage Bart inflicted on him stayed with him for a long while.

At his father’s (first) funeral, Chuck abandoned Blair even though she was standing by his side. He accused Lily of being unfaithful the moments before Bart’s death. And even when Chuck thought that Bart was responsible for the death of an innocent woman, Chuck was complicit in attempting to cover it up.

Betraying His Best Friend

One of Chuck’s most redeeming qualities was his affection for his best friend Nate. Nate supported Chuck through many things, but Blair was something that they could not agree on. Chuck slept with Blair during the time that she was broken up with Nate.

Though not the most egregious offense, Nate presumed that Chuck did this for sport and not because he cared about her. From then on, Nate’s confidence in Chuck had been shaken and they never quite recovered.

Abandoning Blair In Europe

In the culmination of season one, it seemed that Chuck and Blair were going to make it work. Chuck more or less admitted some semblance of feelings for her and they planned to meet in Europe for the summer.

Blair made it there but Chuck never did. He let his father’s words haunt him. Chuck couldn’t handle the fact that he was maturing as a person and Blair was the symbol of that. Instead, he slept with his father’s interior decorator and never told Blair that he wasn’t coming.

Sleeping With Jenny Humphrey

Chuck committed many questionable acts concerning Jenny Humphrey. When they first met, he had no qualms of disrespecting her consent. Even after he tried to make amends for that, he offended again.

After he planned to meet Blair at the Empire State Building, he didn't wait for her when she arrived late. Jenny was also in a vulnerable place after ruining her friendship with everyone on the Upper East Side. Chuck and Jenny’s final encounter was consensual but filled with guilt and dishonesty. Especially when Chuck lied to Blair about his whereabouts after she came looking for him.

Taking Blair For Granted

Blair Chuck Gossip Girl

At Bart Bass’s funeral, Blair promised that she would stand by Chuck through anything. Once they entered into a relationship, he took that to mean that he could act as he wanted without repercussions. This became evident when once again Bart Bass’s ghost came back to haunt him.

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Chuck wanted his legacy to last so when his hotel was threatened, he did what he thought was necessary to make sure he kept it. This meant trading Blair for a night with his uncle. Even after Blair ended things with him, Chuck thought that it would be easy to get past it since she would always be there for him. It took a long time for him to realize his actions caused consequences.

Treatment Of Lily Van Der Woodsen

Lily van der Woodsen was the only female role model that Chuck ever had. Even before she was legally his stepmother, Chuck had a complicated relationship with her. Chuck viewed his only family as his father and his presumed-dead mother. There were times where Chuck accepted Lily’s maternal role, but many times he disrespected her.

Once his father died, Chuck blamed Lily for the accident, even though she was not the cause. It took a long time for them to heal from that event. And even so, their relationship remained consistent with its ups and downs.

His Temper

Nothing would set Chuck off more than losing Blair Waldorf. On many occasions, his emotions got the better of him. From slut-shaming her on Gossip Girl to being the cause of a fight at her Cotillion, Chuck would often act without thinking.

His worst offense was the moment Blair told him that she was marrying Prince Louis. Already drunk and trying to kiss her, the night got worse when he punched a window above her head. The glass cut her face and he was branded a monster for what he did.

Depending On His Romantic Partners To Fix Him

Chuck and Eva prepare to leave Paris for New York in Gossip Girl

Blair was not the first of Chuck’s girlfriends he leaned on too much. While Blair was his best match, he assumed that she would always be there no matter what he did. When he destroyed their relationship, he depended on his next romantic partners to provide meaning to his life.

With French girl Eva, he used her to feel better about himself. She was pure and selfless which he took to mean that she would make him the same. When that didn’t work out he depended on his next girlfriend Raina to help him in business. Chuck used his relationships as a crutch so he didn’t have to take responsibility for his actions.

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