Gossip Girl: The ULTIMATE Serena & Dan Relationship Guide!

Jayson Reinger 10 May 2025

Did the Upper East Side's golden girl and the Brooklyn outsider truly find their happily ever after? The tumultuous relationship of Serena van der Woodsen and Dan Humphrey, affectionately known as "Derena," captivated audiences throughout Gossip Girl's six seasons, leaving many wondering if they ultimately stand the test of time.

The path to potential bliss was far from smooth. In a world of scandalous secrets and ever-shifting alliances, Serena and Dan navigated a minefield of betrayals, insecurities, and social disparities. Their on-again, off-again romance became a defining characteristic of the show, fueling endless speculation and passionate debate among fans. From their initial connection in the pilot episode to the dramatic revelations in the series finale, "Derena" remained a central focal point, constantly raising the question: were they truly meant to be?

Category	Information
Name	Daniel "Dan" Humphrey
Alias	Lonely Boy, Gossip Girl
Portrayed by	Penn Badgley
Series	Gossip Girl
Occupation	Writer, Blogger (as Gossip Girl)
Residence	Brooklyn (initially), Upper East Side (later)
Family	Rufus Humphrey (father), Jenny Humphrey (sister)
Relationships	Serena van der Woodsen (wife), Blair Waldorf (briefly), Vanessa Abrams
Education	St. Jude's School for Boys, NYU
Reference Link	Gossip Girl Wiki - Dan Humphrey

The drama was relentless. Remember the Thanksgiving dinner confrontation? Blair, ever the schemer, accused Dan of cheating on Serena, attempting to dissuade Serena from rekindling their romance. Serena's initial disbelief crumbled as Dan's past actions, particularly his tendency to portray her in a less-than-flattering light through his writing, came to light. This led to a period of ostracization for Dan, highlighting the complex dynamics within their social circle.

The core of Serena and Dan's issues stemmed from deep-seated insecurities. Dan, the outsider from Brooklyn, grappled with his social and financial standing compared to Serena's privileged world. Serena, on the other hand, questioned her own intelligence and worth, constantly seeking validation and fearing she was loved only for her image. These insecurities fueled their conflicts and contributed to the volatile nature of their relationship.

Season 6, the final season, brought renewed hope for "Derena" fans. But even then, the road wasn't easy. Vanessa's revelation about Dan and Blair's kiss created further turmoil, testing Serena's trust and forcing her to confront uncomfortable truths. The machinations of Serena's cousin, Charlie Rhodes, added another layer of complexity, as she attempted to sabotage Serena's relationship with Dan.

Many fans felt that other pairings would have been more fitting. Some argued that Lily and Rufus, despite their own challenges, should have ended up together. Others championed a Serena and Nate endgame, believing their friendship and shared social standing provided a more stable foundation. A segment of viewers felt Dan shouldn't have ended up with anyone, citing his manipulative behavior towards Serena throughout the series. They argued that his sudden desire for her at the end felt contrived and unearned.

Adding another layer of intrigue, the revelation that Dan and Serena shared a sibling, Scott Rosson (Rufus and Lily's love child), further complicated their relationship. Even without Scott's existence, the fact that their parents were in a committed relationship presented a significant hurdle for them to overcome.

Despite the challenges, the narrative ultimately suggested that Serena and Dan were destined to be together. Even the revelation that Dan was Gossip Girl, the anonymous blogger who relentlessly chronicled and often fabricated scandals within their inner circle, couldn't derail their eventual reunion. The series finale offered a glimpse into their future, revealing that they had indeed gotten married.

Flash forward five years: the finale showed that Dan and Serena were still together, suggesting a lasting commitment. A new scene confirmed their continued union five or six years after their wedding, hinting at a stable and loving relationship. However, even in their happily ever after, Georgina Sparks remained a disruptive force, adding a touch of chaos to their lives. The revelation that "this is Dan and Serena's house" underscored their commitment to building a life together.

So, did Serena and Dan get back together in season 6? Yes, they did. Despite the rollercoaster of emotions and betrayals, their relationship ultimately found a resolution. They were able to overcome their issues and reconcile, providing fans with the satisfying conclusion they had long awaited.

Their journey involved numerous detours and temptations. Serena's brief relationship with artist Aaron Rose, who happened to be the son of Blair's new stepdad, added another layer of complexity to their interwoven lives. After things ended with Aaron, Serena found her way back to Dan, highlighting the magnetic pull they had on each other.

The series finale, set five years after their 2012 wedding, revealed that Serena and Dan were not only still together but also had a child. However, their seemingly idyllic life was still punctuated by Georgina's mischievous interference, a reminder that the drama of the Upper East Side never truly fades.

A pivotal moment occurred when Blair brought Nate to a suite, only to find Serena waiting for him. Jealous of their planned meeting, Blair impulsively told Dan, Serena's current boyfriend at the time, that she had slept with Nate. This act of betrayal further complicated the already tangled web of relationships.

Later, Nate confronted Blair, demanding she either forgive him for his past actions or end their relationship. She chose forgiveness, opting to stay together and attempt to rebuild their trust. This subplot highlighted the complexities of forgiveness and reconciliation, themes that resonated throughout the series.

Some viewers argued that Dan and Serena's relationship should have served as a cautionary tale, demonstrating that first loves don't always last. They believed the writers took a "lazy" route by fulfilling the fairytale trope, when a more realistic ending would have seen them move on from each other after the fallout between Blair and Dan. While not advocating for a Blair and Dan pairing, these viewers felt their brief connection was more compelling than the ultimate "Derena" reunion.

At the beginning of one particular episode, Dan and Serena were still apart, with Serena pursuing a relationship with Nate. However, a series of events, including a confrontation with Georgina Sparks and several romantic moments between Dan and Serena, led to a rekindling of their relationship. By the end of the episode, they were officially back together, signaling a renewed commitment to each other.

In a poignant moment, Dan confessed to Serena, "Serena, I know I've hurt you, but I still love you. I've lost track of it at times, I've made mistakes, I've made massive, heartbreaking mistakes, but I've never stopped loving you." This heartfelt declaration, from episode 6x9, echoed a similar sentiment expressed in episode 5x13, solidifying the enduring nature of their feelings.

The relationship between Dan and Serena, "Derena," was central to the narrative of Gossip Girl. Their on-again, off-again romance, fueled by insecurities and external pressures, kept viewers engaged and invested in their ultimate fate. While other couples had their moments in the spotlight, "Derena" remained a constant source of drama and speculation.

Some fans appreciated the exploration of alternative pairings, even if only for a brief period. The temporary connections between Dan and Blair or Serena and Nate added complexity to the storyline and allowed for exploration of different relationship dynamics. "Youre supposed to date other people," one fan argued. "Shows need to keep things exciting and if they just put the endgame couples together they would do far worse things to the relationship and I think enough had been done to Chair and Derena."

The early seasons of Gossip Girl showcased "Vintage Derena," capturing the initial spark and innocence of their relationship. This contrasted sharply with the later seasons, where their romance was plagued by betrayal and mistrust. This shift in tone sparked ongoing debates within the Gossip Girl fan community, with many questioning whether Dan and Serena were truly meant to be together.

The question that lingered in the minds of many viewers: "Are they going to be getting back together next?" This constant anticipation and uncertainty fueled the show's popularity and solidified "Derena" as one of the most talked-about couples in television history.