10 Worst Things Gossip Girl Did To Serena Van Der Woodsen Ranked

Serena van der Woodsen was deemed the “it girl” of Gossip Girl but that doesn’t mean the show didn’t dish out numerous terrible things to her. Best known for being a free-spirit and hopeless romantic, Serena was intriguing both to viewers and the residents of the Upper East Side. Although certainly not a role model, Serena displayed a number of admirable qualities, including having incredibly thick skin and the ability to weather any storm with grace.

These qualities allowed Serena to be able to bounce back from all the horrendous things that happened to her on Gossip Girl. While she was born with a silver spoon in her mouth, she was also dealt a tough family life and a tendency to attract terrible partners as a result of them. All of the glitz and the glamour of her life was not able to make up for the trauma and scandal she faced during Gossip Girl‘s 7-season run.

10 Serena’s Cousin Was An Imposter

Season 4, Episode 18, “The Kids Stay In The Picture”

Serena’s cousin, Charlie, ended up not being who she said she was. Instead of actually being a member of the family, it turned out that she was an actress whom Serena’s aunt paid to impersonate her daughter and get access to her trust fund. It came as a huge surprise to Serena when the truth came out because she had taken “Charlie” under her wing and treated her like a sister. It also later was revealed that her real cousin was actually her half-sister, and her dad had an affair. Given that so many people betrayed Serena on Gossip Girl, it was very unfortunate that this situation left her questioning the integrity of her family as well.

9 Serena’s Best Friend Started Dating The Love Of Her Life

Season 5, Episode 16, “Cross Rhodes”

Serena dated numerous people on Gossip Girl, but her heart always belonged to Dan. That’s why it came as such a betrayal when Blair started dating him. Serena was forced to stand by and watch as her best friend and the love of her life got together and excluded her from their social circle. Neither Serena nor Blair was entirely innocent during the course of their friendship and they both did unspeakable things to one another, but this felt like crossing the line. Serena would never have dated Chuck because it would have broken Blair’s heart, so it was damaging to see Blair not display the same loyalty.

8 Serena’s Dad Left Her & Didn’t Want To See Her

Season 3, Episode 1, “Reversals Of Fortune”

Serena and her brother, Eric, really got the short end of the stick when it comes to parents. Their dad left them when they were little, and their mother was constantly choosing the men in her life over her children. To add insult to injury, when Serena decided to look for her father and finally found him, he turned her away. The parental neglect in her life gave her abandonment issues that permeated all of her relationships, making it a terrible thing for Gossip Girl to do to her.

7 Serena’s Boyfriend Left Her Alone After A Car Accident

Season 3, Episode 12, “The Debarted”

Serena’s entire relationship with Tripp van der Bilt, Nate’s cousin, was tragic and unhealthy. Tripp was married and Serena’s boss when the two started developing feelings for one another. When the pair decided to run away for the weekend and get away from the city, Tripp ends up leaving her in their cabin to talk to his wife. He and his wife ended up coming to the conclusion that Serena could be his mistress, and they would remain married to keep up public perception. This was heart-breaking to Serena and when she demanded he drive her home, they got into a bad car accident.

Instead of making sure Serena was okay, Tripp fled the scene to avoid any trouble. This meant that Serena was not only betrayed by Tripp wanting to remain married to his wife but also by being left when she was hurt. His wife was also blackmailing Serena and her mom the entire time, putting Serena in an incredibly difficult position.

6 Serena Found Out Her And Her Brother Shared A Sibling

Season 3, Episode 5, “Rufus Getting Married”

Given how much Serena loved Dan, the storyline involving their parents being romantically intertwined was simply gut-wrenching. It was bad enough when they found out their parents had dated before they met and when they later got married, but learning that they had a love child was just too much. The truth came out when the pair was in high school, leading to a lot of humiliation on top of Serena trying to navigate her own feelings about the situation and how it impacted her relationship with Dan. The entire plot line of the shared sibling felt unnecessarily cruel to Serena especially because it didn’t end up getting revisited.

5 Serena’s Mom Sent Her Innocent Teacher To Jail

Season 4, Episode 3, “The Undergraduates”

In one of the most shocking and appalling chapters of Gossip Girl, it was learned that Serena’s mom, Lily, sent an innocent man to jail. The man was Serena’s teacher, one that she felt extremely connected to and had a crush on. Lily took note of this fact and told the school that the two were in a relationship, a fact that was completely untrue, in order to prevent Serena from being suspended. Not only did Lily lie, but she forged Serena’s signature on the affidavit.

When the truth came out, Serena was furious as her favorite teacher had spent years in prison, and he spent that time thinking she was the reason why. The situation was incredibly difficult and complicated for her, as she ended up beginning a relationship with the teacher after he was released from prison, and she was forced to navigate protecting her mom from getting in serious trouble and her feelings for him. Other people caught wind of what had happened and even started blackmailing Lily, adding even more stress to Serena’s life.

4 Serena Was Blackmailed By Georgina

Season 1, Episode 15, “Desperately Seeking Serena”

Serena was plagued with guilt for years after a man died from a line of cocaine she offered to him, and Georgina decided to exploit that. She began blackmailing Serena and putting her in extremely uncomfortable positions, like sending porn to her family’s home and outing her little brother. Georgina even went so far as to roofie Serena’s drink, causing her to miss out on taking her SAT. The situation ended up taking a serious toll on Serena and Dan’s relationship, leading them to break up. Having Serena’s guilt used so maliciously was an awful thing to do to her and left her further traumatized by what had happened.

3 Serena’s Dad Gave Her Mom Fake Cancer

Season 3, Episode 19, “Dr. Estrangeloved”

One of the absolute worst things to happen to Serena on the show was when her father came back and gave her mother fake cancer to try to win her back. He wanted to diagnose her with an illness and then “cure” it to make her feel like he saved her life. Serena was left extremely worried about her mother and her health for no reason, as her father exploited her concern to get back into her life. After the truth was discovered, Serena gave him the opportunity to run away, so he wouldn’t get in trouble with the police, and he took it – leaving her fatherless once again.

2 Serena Was Drugged & Sent To Rehab

Season 4, Episode 10, “Gaslit”

As if the situation with Serena’s teacher, Ben, wasn’t bad enough, his sister, Juliet, decided she wanted revenge for it. Before Ben and Juliet knew that it was Lily who was responsible for the jail time, the two created a plan to make Serena pay. Juliet infiltrated Serena’s social circle, causing the people closest to her to turn against her. The plan escalated when Juliet decided to drug Serena and take staged pictures that made it look like she was on a bender.

This led to Serena’s mom involuntarily sending her to rehab, leaving Serena feeling confused and hurt. Serena had struggled with drugs in the past, so capitalizing on her vulnerabilities like this and making her believe she had a serious problem was unfair on so many levels. It made her question herself and all of the progress she had made thus far, making it one of the most horrible things to happen to her on the show.

1 Serena’s Entire Life Was Chronicled By Gossip Girl

Season 1 – Season 6

While all of the aforementioned things that Gossip Girl did to Serena were extremely problematic and terrible, the worst of the worst was having it all chronicled online. This allowed all of her peers to judge and weigh in on all of these difficult situations, making them even harder to deal with. The fact that Gossip Girl was Dan all along, someone she felt so loved by and comfortable with, made it all worse. Serena did not deserve to have her every move under a microscope and to spend her formative years being attacked online.