In season 1 of Gossip Girl, Chuck Bass was about seventeen years old. He was a troubled bad boy who resorted to unhealthy coping mechanisms to dull the pain left by his mother's death and his father's disapproval of him. Like a typical teenager, he acted in self-serving ways. He treated women as objects and sought attention by drinking and getting in trouble.
After his father's premature death, Chuck had no choice but to grow up. His father left him a fortune and rather than spending it all carelessly, Chuck started building his own empire. While some of his destructive patterns persisted until the very end, he also surprised the audience by acting wise beyond his years.
10 Teenager: When He Assaulted Jenny
When Chuck Bass is introduced in the first episode of Gossip Girl, he acts like a complete brat. He was essentially a predator; first, he made inappropriate comments to Serena and later on pursued and assaulted the naive 14-year-old newcomer, Jenny Humphrey.
Teenagers want validation and attention from their peers, but needless to say, not all of them are predators in the making. Chuck, on the other hand, took what he wanted without considering other people's personal boundaries. He managed his emotions by resorting to self-destructive behaviors, such as drinking and sleeping around.
9 Wise: When He Bought The Empire Hotel
With his father gone, Chuck had to grow up fast. He was just a teenager when he became a stockholder in his father's company, Bass Industries. In "The Lost Boy", he decided to sell his shares to buy The Empire Hotel.
Season 3 Chuck was a great partner to Blair. He was serious about work, honest, responsible, and wanted to bring her up when she was feeling down.
8 Teenager: When He Acted Out At His Father's Funeral
Bart Bass died in season 2. Even though the two didn't get along (or precisely because of that), Chuck spiraled out of control afterward. Even responsible adults regress to childlike states in the face of death and Chuck was no different.
He rejected Blair's help and talked back to everybody who reached out. The tantrum didn't last long because he had bigger fish to fry. Jack wanted to take over the business, so Chuck had to team up with Lily and fight for the right to his father's legacy.
7 Wise: When He Accepted His Mother Into His Life
Chuck's parents made some of the worst parenting choices in the entire series. For his entire life, Chuck believed that his mother died at childbirth and blamed himself for her death, but when she unexpectedly came back into his life in season 3, he welcomed her with grace.
This is Gossip Girl, though, so it turned out that Chuck made a mistake by trusting her and letting her back into his life. She only came back because she wanted money. Before long, she disappeared again.
6 Teenager: Every Time He Tipped Off Gossip Girl
Chuck tipped off Gossip Girl several times in the show, even though the cyberbully was the group's biggest enemy. He tarnished Blair's reputation by telling the world that she slept both with him and Nate. And that's not even the worst thing he ever did to her.
All teenagers have to learn how to manage intense emotions, which is definitely not an easy task. Chuck Bass was particularly emotionally unstable - he was aggressive towards Blair and verbally abusive to most people in his life.
5 Wise: When He Went To See A Therapist
In "The Fasting and the Furious", Chuck did what was long overdue: he started therapy. He hoped that professional help might assist him in finally letting go of Blair who was in a relationship with Louis.
Being a responsible adult certainly doesn't pay off on the Upper East Side, though. It turned out that Louis bribed Chuck's therapist, hoping that therapy would somehow push Chuck's buttons and make him angry enough to push Blair away for good.
4 Teenager: When He Got Drunk & Crashed Blair's Ball
When Blair found happiness with Louis, Chuck couldn't live with himself. He crashed Blair's ball, got drunk, and told Blair's future mother-in-law that they belong together.
Chuck made enough of a scene to get thrown out of the party, so he went back to his beloved Empire to sulk. Later that night, Blair came and told him that Louis proposed to her. It's hard to say who was more immature in that episode; but Chuck getting drunk and embarrassing himself, later mistreating Blair, takes the cake.
3 Wise: When He Gave Blair & Louis His Blessing
Chuck and Blair had a nonsensical relationship, filled with manipulation, aggression, and reckless passion. In "The Wrong Goodbye", Blair almost broke up with Louis to be with Chuck, but he advised her against it. He even admitted to feeling guilty about the whole situation, which is something that season 1 Chuck would never say.
He told Blair that he will always love her and let her go. It was the mature thing to do since their relationship was so unhealthy. It wasn't long until Blair and Chuck ended up together again, though.
2 Teenager: When He Moved In With The Van Der Woodsens
After Lily and Bart got together, Chuck and Serena became step-siblings. While Chuck was nice enough to Eric, he was driving Serena crazy.
Leaving aside the fact that these teenagers were privileged enough to all have their own bathrooms, Chuck was invading Serena's personal space by smoking weed in her bathroom. Serena had enough issues with substance abuse as it was, so it was really inconsiderate of Chuck to provoke her like that.
1 Wise: When He Outsmarted Bart
One of the show's most hated storylines was Bart Bass coming back from the dead and attempting to kill his one and only son in a staged plane crash. Bart was a master manipulator who pulled off faking his own death, but Chuck was even smarter than him.
Chuck was only in his early twenties at that time, but he played mind games better than all the parents combined. It's not necessarily a sign of maturity, but it's definitely the type of wisdom that comes in handy in Gossip Girl.
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February 26, 2021 at 11:00AM
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Gossip Girl: 5 Times Chuck Acted Like A Typical Teenager (& 5 He Was Wise Beyond His Years) - Screen Rant
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