Gossip Girl's Dan & Serena: A Toxic Love Story? [Timeline]

Mina Boehm 08 May 2025

Is it possible to truly define a relationship as tumultuous and captivating as that of Dan Humphrey and Serena van der Woodsen? Their on-again, off-again romance on Gossip Girl became a cultural phenomenon, a guilty pleasure, and a source of endless debate. From stolen glances in the halls of Constance Billard and St. Judes to a wedding witnessed by millions, "Derena," as they were affectionately (or perhaps derisively) known, etched themselves into the annals of television history.

The journey of Dan and Serena is anything but linear. It's a maze of betrayals, reconciliations, and questionable decisions, all played out under the watchful eye of Gossip Girl. Their connection, however, resonated with many, capturing the messy reality of young love, ambition, and the relentless pursuit of acceptance. Despite the complications, the show ultimately posited them as endgame, a notion that sparked both celebration and outrage among viewers. But how many times did Serena and dan date, really? And what were the circumstances that led them back to each other, time and time again?

Attribute	Information
Full Name	Daniel "Dan" Humphrey
Portrayed By	Penn Badgley
Alias	Lonely Boy, Gossip Girl
Occupation(s)	Writer, Blogger
Love Interests	Serena van der Woodsen, Blair Waldorf, Georgina Sparks, Olivia Burke, Rachel Carr
Family	Rufus Humphrey (father), Lily van der Woodsen (stepmother), Jenny Humphrey (sister)
Series Debut	Pilot
Series Finale	New York, I Love You XOXO
Marital Status	Married to Serena van der Woodsen
Website	IMDB - Gossip Girl

Their story begins, fittingly, with a chance encounter. In the pilot episode, at the Palace Hotel, a fumble leads to a returned cell phone, and an invitation. Serena, the It Girl, asks Dan, the outsider, on a date. It's a fairytale beginning, seemingly defying the rigid social strata of the Upper East Side. They date throughout the first season, navigating the challenges of their vastly different worlds. The season culminates in a breakup during "Much 'I Do' About Nothing," a dramatic episode filled with revelations and heartbreak.

However, this separation proves fleeting. Before the credits even roll on the next episode, they're back together, their connection proving too strong to resist. This pattern of rapid reconciliation sets the stage for their future. The second season introduces a temporary detour, a charade. Nate and Serena pretend to date, a ruse to help Serena recover from her split with Dan and to conceal Nate's affair with Catherine. This dalliance, while brief, underscores the undercurrent of attraction that exists between Serena and Nate, further complicating the romantic landscape.

Season three throws new obstacles in their path. Serena begins dating artist Aaron Rose, the son of Blair's new stepfather, Cyrus. This relationship adds another layer of intrigue, intertwining their personal lives with the intricate web of family connections. After things fizzle out with Aaron, Serena finds herself drawn back to Dan, reigniting their familiar flame. They attempt to navigate the complexities of their past, but old wounds and unresolved issues continue to surface.

Do Dan and serena get together season 4? The answer is a resounding yes, albeit temporarily. Their reunion is short-lived; trapped in an elevator, their unresolved issues reach a boiling point, leading to another breakup. This particular separation highlights the cyclical nature of their relationship, a constant push and pull fueled by both genuine affection and deep-seated insecurities.

The later seasons further test their bond. Season five finds Serena pining for Dan, but his affections are directed towards Blair. This unrequited longing adds a layer of melancholy to Serena's character, showcasing her vulnerability and her enduring feelings for Dan. They do, however, hook up again, a fleeting moment of passion that serves as a reminder of their undeniable chemistry.

Season six brings yet another chapter in their saga. They briefly date, for what feels like a week, but Dan's motives are far from romantic. He's using the relationship as fodder for his book, a betrayal that deeply wounds Serena. This act underscores the somewhat toxic nature of their relationship, highlighting Dan's tendency to prioritize his ambition over Serena's feelings. Despite this egregious transgression, Serena, in a move that baffles some viewers, ultimately forgives him.

The intricacies of season six often fade in the memory, overshadowed by the revelation of Dan as Gossip Girl. However, during episode 2 of season 6, the couple does engage in dating. This act of forgiveness, or perhaps acceptance, is crucial to their eventual reconciliation. It speaks to Serena's capacity for empathy and her willingness to see the good in Dan, even when he falters.

Throughout the series, there are instances where they are simply friends. In the end of season 1, they are seen together as friends welcoming summer. Their friendship mends throughout the seasons, providing a foundation for their intermittent romantic entanglements. The "benefit," as some might call it, is that even when they're not romantically involved, they share a deep connection, enjoying familiar activities and each other's company.

Eating pierogies and going to see "Ugetsu" for the sixth time are activities made infinitely better because they can experience them together, as girlfriend and boyfriend. This shared history and these familiar rituals bind them together, creating a sense of comfort and belonging that transcends their romantic status.

The dynamic between Dan and Serena is further complicated by their families. Serena starts dating outsider Dan Humphreyexcept they don't know that Dan's father, Rufus Humphrey, used to date Serena's mom, Lily van der Woodsen, a long time ago. This revelation adds a layer of soap opera-esque drama to their relationship. Many "Gossip Girl" fans disapproved of Rufus and Lily rekindling their romance while their children were dating, and ultimately marrying. The idea of step-siblings dating while their parents are still married raises ethical questions, yet none of the characters seemed to think it was wrong, and Rufus and Lily encouraged Dan and Serena to pursue each other. They even shared a sibling!

The HBO Max "Gossip Girl" reboot offered a glimpse into the lives of Dan Humphrey (Penn Badgley) and Serena van der Woodsen (Blake Lively) after the original series ended. This new scene confirmed that Dan and Serena are still together about five or six years after their wedding in Gossip Girls finale. The original series ended with a flash forward five, indicating their enduring commitment to each other.

Their relationship wasn't the only one that divided viewers. Serena and Blairs husbands arent good people, but neither are Serena and Blair. Blairs future husband Chuck rapey Bass literally sold her for a building, committed domestic violence, and hurt her far worse every season than Dan ever hurt Serena. The complexities of these relationships, including that of Dan and Serena, are sold to us as a great love thats the show.

Serena and dan and whatever romantic potential they had was hurt way more by their parent hooking up then anything dan and blair did. The only thing blair and dan took hatchet to was chuck and blair because it showed blair in a relationship built on mutual respect and compassion as opposed to the manipulation and constant need to sabotage each From blair to serena, many of the main characters in gossip girl weren't with the right person.

Ultimately, the question of how many times Dan and Serena dated becomes secondary to the larger narrative of their enduring connection. Their relationship is a tapestry woven with threads of love, betrayal, forgiveness, and ambition. It's a messy, imperfect, and ultimately captivating story that continues to resonate with viewers years after the final episode aired. Despite the somewhat toxic nature of serena and dans relationship in later seasons, the couple that seemed destined to be together did make it happen despite dan being gossip girl, despite From the start, both dan and serena are in search for love, control and power, whether over themselves, their city or their enemies.

The "Derena complex," as some might call it, truly is the foundation for the entire series. Here's which couples should've been endgame. Like dan and serena, they are sold to us as a great love thats the show. Max and serena were over before they even started. Serena and dan went through multiple breakups along the way on gossip girl before ultimately ending up together. Since dan and serena were always meant to be endgame, the shows finale ended on their beautiful wedding day.

Dan humphrey is only one of gossip girl's many characters, but he's incredibly important to the story and has a number of key love interests. Rachel carr is a recurring character in season two of the gossip girl television adaptation. She is portrayed by laura breckenridge. In you've got yale!, serena introduces dan to her new shakespeare teacher, rachel. They begin dating for all of the first season before breaking up in much 'i do' about nothing.