XOXO Gossip Girl: The Most Shocking Betrayals Between Dan and Serena

Summary

Dan and Serena's relationship on Gossip Girl was plagued by terrible behavior, with Dan slut-shaming Serena and secretly being the infamous Gossip Girl.

Throughout the series, Dan and Serena repeatedly reunited, exacerbating the pain and harm inflicted upon themselves and those in their vicinity. Serena consistently demonstrated her selfishness by neglecting to take Dan's viewpoint into account, often prioritizing her own desires and leaving him to bear the brunt of the repercussions stemming from her behaviour.

The romance between Dan Humphrey and Serena Van Der Woodsen on Gossip Girl was a captivating love story, filled with two flawed individuals who constantly hurt each other. Initially, they were sweet and fans were hopeful for an epic romance. However, they soon learned the harsh reality of why they were not meant to be together. Sadly, both of them became villains, saying and doing terrible things to one another. In Gossip Girl, characters often bring out the worst in themselves, and Dan and Serena perfectly exemplify this.

Although Gossip Girl has been reinvented for a new generation on Max, the new series still maintains a strong connection to the original. This is largely due to the presence of characters who were central to the CW series. While Serena and Dan may not be interacting with the new group of teenagers on the Upper East Side, their complicated relationship served as a crucial element in the foundation of the original show. Regardless of the numerous hardships they faced, Dan and Serena repeatedly found their way back to each other.

The Worst Things Dan Did To Serena In Gossip Girl

Right from the outset of the series, it became evident that Serena was a spirited young lady driven by her passions. She fearlessly delved into her emotions, regardless of their nature, and accepted responsibility for any errors she committed on her journey. Conversely, Dan insisted on reminding her to not forget what he perceived as her "missteps."

Dan Slut-Shamed Serena Numerous Times

Serena's previous partners were dismissed by Dan as errors, but the audience viewed them as an integral part of her past. As she navigated through life, Serena engaged in several short-lived relationships, each serving as a stepping stone towards self-discovery. Dan, assuming the persona of Gossip Girl, publicly condemned these romantic entanglements, whether it be at social gatherings, within the confines of their high school corridors, or even amongst their circle of friends. He consistently portrayed Serena's romantic history as problematic and something she should feel ashamed of.

In his role as Gossip Girl, Dan subjected Serena and her friends to years of continuous stalking, causing immense distress. Astonishingly, even in private, Dan would feign ignorance and react with feigned surprise while secretly indulging in the scandalous posts. It was not spared from Gossip Girl's relentless scrutiny either, Dan and Serena's relationship becoming a prime focus for the blog.

Dan Was Gossip Girl

However, the most surprising aspect is that Dan consistently evaded accountability for the aftermath caused by Gossip Girl. Each time he contributed to the website, he shrewdly shifted the blame onto someone else. Maintaining the continuity of Gossip Girl took precedence over his professed devotion to Serena, the woman he claimed to be his one true love.

Not only did Dan consistently criticize Serena's relationships throughout the series and hypocritically judge her romances with teachers, but he also publicly exposed her for buying a pregnancy test. Interestingly, the identity of the person who revealed this on Gossip Girl's blog remained unknown until later on.

Dan Outs Serena’s Purchase Of A Pregnancy Test

Serena's purchase of a pregnancy test coincided with the official start of her relationship with Dan in the first season. Rather than keeping this information to himself, Dan decided to use it for a Gossip Girl post. Feigning surprise, he read the post in front of his father and sister, creating a widespread rumor mill about Serena throughout the school. However, Dan's actions didn't just harm Serena, but also himself, as he was her boyfriend at the time. Despite the potential damage to his own reputation, Dan was willing to sacrifice it in order to provoke judgment on Serena's choices.

Despite all of Dan's lectures on relationships, he did not live up to the innocent lifestyle he expected of Serena. In fact, he betrayed his childhood best friend Vanessa by spending the night with Serena while still dating her.

Dan Used Serena To Cheat On Vanessa

Dan's actions reveal the height of hypocrisy as he never hesitated to criticize Serena for her romantic endeavors or swift transitions to new relationships. Ironically, he experiences profound emotional distress whenever she decides to be with someone other than him, or when she divides her attention between him and someone else.

Both Dan and Serena were involved in romantic entanglements with their teachers during the entire duration of Gossip Girl. Dan, known for his hypocrisy with a capital H, made a tremendous fuss over Serena's alleged affair with her teacher, Ben, when she attended boarding school. However, it was subsequently revealed that Serena had only harbored a crush on him, and it was Lily who fabricated the rumor of them sleeping together in order to protect Serena's reputation.

When Serena introduces Dan to her Shakespeare teacher, Dan becomes infatuated with her. Despite Blair's false rumors about Dan and the teacher having a romantic affair, ultimately, they do end up sleeping together and are discovered in the act.

Dan Slept With His Teacher

Georgina was more than just Serena's frenemy; she was her sworn enemy. Following yet another breakup between Dan and Serena, Dan unknowingly fell into a relationship with Georgina and even slept with her. Initially unaware of Georgina's true identity, Dan eventually discovered the truth but remained surprisingly unfazed. Despite denying any intimate involvement, it was evident that they had been together when Georgina later appeared, pregnant with Dan's child, and he believed it was his own.

Dan is free to make his own choice of sexual partners, but sleeping with Serena's sworn enemy was crushing for her.

Dan Slept With Georgina

Dating Blair Waldorf, Serena's best friend, turns out to be even more disastrous than sleeping with her arch-nemesis. The initial animosity between the two adds an intriguing twist to this peculiar storyline.

They connect through their shared interests in movies and art, as well as their deep concern for Serena, of all people. Both of them regretfully failed to be honest with Serena about their growing feelings, resulting in a terrible outcome. Despite their efforts to shield Serena from hurt by keeping their blossoming relationship hidden, they unintentionally caused her pain.

Dan Dated Blair

Dan, the tormented writer, eventually secured the long-awaited publishing contract of his dreams. However, was it worth it? The content revolved around his circle of acquaintances residing in the upscale neighborhood of the Upper East Side, their identities haphazardly disguised under names vaguely resembling their real-life counterparts. In one fateful stroke, he succeeded in estranging his entire enclave of friends and family from the Upper East Side.

The Worst Things Serena Did To Dan In Gossip Girl

The most unfortunate aspect of it all was that the protagonist of the book bore the name Sabrina and was fashioned after Dan's supposed true love. As a consequence of the book's publication, Serena not only suffered the loss of her coveted Hollywood job, but it also proved to be a devastating blow to her professional life. To make matters worse, Dan, the self-proclaimed "nice guy," appeared to display absolutely no hint of remorse.

Dan Writes A Scathing Novel, Starring Serena

Chuck's father's death led Serena to invite Dan to accompany her to the funeral. However, Chuck expressed his disapproval of Dan's presence, as the two had never gotten along despite sharing the same friend group. Despite this knowledge, Serena persisted in her request for Dan to be by her side during the funeral.

Dan found himself in an uncomfortable situation as he stood amidst the Bass family and their business associates, with Serena, her grandmother, Chuck, and himself engaged in a heated argument. Even Serena's grandmother acknowledged Chuck's irrational behavior but emphasized that since it was his father who had passed away, Serena should respect the wishes of the Bass family, as she was there to support them. However, Serena persisted in her petulance, placing Dan in the middle of the argument and disregarding the emotions of others and the consequences it entailed for Dan.

Serena Puts Dan In An Awkward Position At A Funeral

In order to seek revenge on Blair and Dan for their relationship, Serena opted to create a film capturing her intimate encounter with Dan. The sex tape held a powerful threat, waiting to ignite an explosive drama. Surprisingly, instead of severing ties with Serena after the tape was revealed to a shocked Cotillion crowd, Dan chose to spend the night with her and reconcile. Unfortunately, little consideration was given to Blair, who was equally affected by the tape. Although Dan successfully managed to win Serena back, he once again became a target of the Upper East Siders for his actions.

Serena Filmed Her And Dan Sleeping Together

Jenny, Dan's beloved younger sister, simply desired a low-key birthday celebration with her close friends. However, Serena, in her quest to dispel any notion of an affair with Blair's former flame, Nate Archibald, transformed Jenny's birthday into the ultimate excuse for an extravagant party.

Little did anyone know that this seemingly innocent gathering would catapult Jenny into the merciless realm of high school popularity, leading her down a treacherous path of deceit, substance abuse, and eventual dropout. Did Serena extend a helping hand to Jenny during her darkest moments? Regrettably not—she was right there, alongside everyone else, relishing in Jenny's misfortune.

Serena Turned Dan's Sister Into A Monster

Serena's actions, ranging from cheating to running away, have tested Dan's resilience and would deter even the most determined individual. How much can one person endure in the name of true love? Despite Serena repeatedly leaving him for others and evading her own feelings, Dan and Serena somehow managed to stay together.

The most surprising aspect, however, is that despite all the hurt they caused each other throughout the years, they eventually got married and embarked on a journey of everlasting happiness. This may leave even the most devoted Gossip Girl fans questioning whether Dan and Serena could maintain a fulfilling and healthy marriage after all they went through.

Serena Continually Lets Dan Down

Serena's character was adored by fans until season 3, when her charming personality took a dramatic turn as she transformed into an excessively entitled socialite, craving undivided attention. The promises she made to change in the initial season of Gossip Girl were completely disregarded by the time season 3 rolled around.

Dan was constantly discarded like garbage whenever Serena embarked on a new romantic relationship. Furthermore, whenever Serena found herself in trouble, she would opt to escape and vanish to a different country for weeks on end, leaving Dan tormented by worry and uncertainty about her whereabouts.

Serena Only Thinks About Herself

From the beginning of the series, Serena came across as a privileged individual from the Upper East Side, exuding sweetness and care. Dan, on the other hand, though not poor, had fewer opportunities and wasn't handed everything like Serena, who was born into luxury.

But did Serena ever try to empathize with Dan's situation? Not really. She was often too preoccupied with her own problems and schemes to consider the fact that Dan had a less privileged upbringing. It's not that she needed to tiptoe around forever, but she should have taken a moment to understand Dan's perspective, given their different social classes. Their completely contrasting viewpoints caused as much harm as help in their relationship on Gossip Girl.