It's one thing to see teenagers behave in irresponsible and aggressive ways, it's another when their parents are no better themselves. No wonder Serena, Blair, Chuck, Dan, and the rest of the Gossip Girl squad sometimes lashed out and acted in self-destructive ways; their parents made for pretty bad role models.
The parents had some really interesting storylines along the way and most of them showcase just how bad they were at parenting. Rather than dealing with their children and their struggles themselves, they threw their money at them, while thinking they're doing them a favor by avoiding confrontation.
Eleanor Waldorf Bullied Her Daughter
Eleanor was arguably the best mother figure in Gossip Girl, but she was far from perfect. It's no wonder that Blair grew up to be a bully with no comparison - she learned a lot from her mother. Both Eleanor and Blair bullied Jenny, just because she was an easy target.
In the beginning, Eleanor and Blair were always snarky and mean towards one another. Blair was a teenager, but what was Eleanor's excuse?
CeCe Faked Being Ill
Serena's grandmother CeCe was even more manipulative than Lily. She lied about having lung cancer in order to guilt Lily into making Serena come to the Debutante Ball. This woman was well into her sixties, yet she meddled in Serena's love life as if she were a teenager herself.
CeCe also made quite an exit, stirring up drama from beyond her grave. When Lily found out that she left everything to Ivy, all hell broke loose.
Lily Was Ashamed Of Eric
Serena's younger brother wasn't as cool as her, and Lily was pretty openly ashamed of him. She wasn't too thrilled about the fact that he was gay. It was hard for him to come out, but she was only concerned about how such news reflected on her.
With a mother like Lily, it comes as no surprise that Eric struggled with mental health. Lily was ashamed of the fact that Eric was struggling rather than showing her care and support.
Howard Archibald Abandoned His Family
Nate's father Howard was also a disappointment. He struggled with substance abuse and Nate took it upon himself to try to help him. Not only did Howard abandon his family, but he also took the money that was in Nate's trust fund, and punched him before leaving for good.
In season 4, Howard lived with Nate. The roles of the child and parent were reversed once again. While Howard was out partying, Nate was worrying whether his father would take the responsibility for himself and go to a job interview.
Scott: The Forgotten Child
Back when Lily and Rufus were madly in love, Lily got pregnant. She decided to keep the baby, not tell Rufus, and pretend the child never happened.
As if Lily's denial wasn't bad enough, Rufus decided to go to Boston and meet his son as soon as he found out the truth. He never stopped to consider whether that would be in Scott's best interest.
Rufus Hooked Up With Ivy
Rufus had many qualities that arguably make him the best father figure in the entire show: he was emotionally available, kind, and concerned. However, he also shared a passionate moment or two with Ivy, Serena's cousin. Obsessing over Rhodes/Van Der Woodsen ladies runs in the Humphrey blood, so Rufus' attraction towards Ivy didn't come as a surprise.
He should have considered his son's emotions and refrain from regressing to a confused teenager himself - hooking up with Ivy was just plain weird! He was supposed to act like an adult, but just like most other parents in Gossip Girl, failed to do so.
Bart Bass Blamed Chuck For His Wife's Death
No sound person would ever blame a baby for the death of the mother in labor. If anything, that poor child would need extra love and care since he would never get to know his mother. Bart hated Chuck for killing his wife and was always stone-cold towards him.
No wonder he is one of the show's least-liked characters. Bart and Chuck thoroughly avoided each other. When they met, Bart would only express his disappointment.
... And Then Faked His Own Death
Even though Chuck didn't have a good relationship with his father, he was still his only family member. When he died, Chuck was devastated. He could no longer hope that one day, his father might come around or that he will prove him wrong.
But as if the trauma of losing Bart wasn't enough, it turned out that Bart was very much alive. Blair ran into him at some party - how could he hide such a thing from his own son?
Elizabeth Fisher Should Have Stayed Dead
Not only was Chuck unfairly blamed for his mother's death, but it also turned out that she wasn't even dead in the first place. What kind of a parent disappears off the face of the earth only to come back nearly two decades later? Elizabeth didn't do Chuck any favors by suddenly showing up in his life.
No wonder Chuck grew into a creepy predator; he looked for love in all the wrong places, which is why he is actually one of the saddest characters on the show.
Lily Always Assumed The Worst Of Serena
Lily Van Der Woodsen seems like a gentle and kind creature, but she actually did some truly unforgivable things. The worst one is probably what she did to Ben Donovan, Serena's favorite teacher. Rather than giving Serena the benefit of the doubt when trying to figure out whether the rumors about their supposed relationship are true, she forged her daughter's signature and thus sent Ben to prison for statutory rape.
It is Lily who should have gone to jail, together with most other Gossip Girl characters. Lily also had Serena committed to the Ostroff Center - that institution was more of a parent to both of her children than she ever was.