Gossip Girl Cast: Who Dated Who Behind the Scenes?

The iconic series 'Gossip Girl' has captured the hearts of viewers since it first aired in 2007. With its engaging narrative and drama-filled plot, the show explored the lives of privileged teenagers on Manhattan's Upper East Side as they navigated friendship, love, and the many challenges of adolescence. However, what many fans didn't realize is that some of the on-screen romances spilled over into real life. In this article, we take a deep dive into the intricate web of relationships among the cast of 'Gossip Girl' and reveal who dated whom behind the scenes.

One of the most captivating aspects of 'Gossip Girl' was its depiction of romantic relationships that resonated with its audience, and while the characters had tumultuous loves, the actors themselves had their share of on-set romances as well. The chemistry exhibited on-screen was often a reflection of their off-screen relationships, creating an enigmatic blend of reality and fiction that fans loved. From Blake Lively and Penn Badgley's romance to Leighton Meester and Sebastian Stan's budding relationship, the cast's love life added to the intrigue of their characters.

As we look back at the series that shaped a generation of television fans, it's essential to uncover the real love stories that happened outside the camera's lens. Join us as we explore the significant relationships among the cast, detailing how their experiences on set influenced their personal lives.

Blake Lively and Penn Badgley: A Real-Life Romance

Blake Lively and Penn Badgley portrayed the on-again, off-again couple Serena van der Woodsen and Dan Humphrey, capturing viewers' hearts throughout the series. Their chemistry was electric, not only on screen but off screen as well, leading to a real-life romance that blossomed during the show's early seasons. Their relationship began around 2007, shortly after the show's premiere, quickly becoming a fan favorite.

Lively and Badgley were frequently spotted together at public events, and their connection was palpable. The young couple seemed inseparable, providing a glimpse into a genuine relationship amidst the fictional drama of 'Gossip Girl.' Badgley reminisced about how their relationship helped him navigate the sudden fame that came with the show's success, stating that Lively's supportive nature kept him grounded.

Despite their breakup in 2010, Lively and Badgley maintained a professional relationship while still working together on set, proving that their bond went beyond just the romantic feelings. Both moved on to other relationships; Lively eventually married Ryan Reynolds, while Badgley found love with Domino Kirke.

Leighton Meester and Sebastian Stan: A Love Story

Another noteworthy romance from the cast was between Leighton Meester and Sebastian Stan. While Stan had guest appearances on the show as Carter Baizen, he and Meester began dating in real life after being spotted together at several events. Their relationship drew media attention, and they soon became known for their affectionate demeanor towards one another.

In interviews, Stan expressed his admiration for Meester, highlighting her talent and intelligence as key aspects of their attraction. Their relationship flourished while they worked together on set, leading to shared experiences that further deepened their connection. However, the romance was short-lived, as they separated in 2010, with Meester reflecting on the emotional difficulties of their breakup.

Although their romance came to an end, both actors have since moved on, with Meester marrying fellow actor Adam Brody and starting a family, while Stan has also been involved in high-profile relationships. The memories of their brief but passionate romance remain part of 'Gossip Girl's' rich history.

Ed Westwick and Jessica Szohr: An On-Again, Off-Again Affair

Ed Westwick and Jessica Szohr shared a passionate relationship while portraying Chuck Bass and Vanessa Abrams on 'Gossip Girl.' Their characters' romantic tension mirrored their real-life connection, which began in 2008. The pair initially kept their romance under wraps but eventually became a subject of media speculation when they were seen together out on the town.

Much like their on-screen characters, their relationship was marked by ups and downs. Szohr has discussed how they shared a desire for privacy but struggled with the public's fascination with their relationship. Over the years, they broke up multiple times before finally ending their romance in 2010. Despite the tumultuous nature of their relationship, both actors have remained amicable and supportive of each other since their split.

Since their time on 'Gossip Girl,' Szohr welcomed a child with her husband, while Westwick has continued his acting career. Their time together remains a fan-favorite topic among those nostalgic for the early 2000s' television era.

Taylor Momsen and Chace Crawford: Rumors and Denials

In the world of 'Gossip Girl,' rumors often swirled regarding various cast relationships, and one such rumor involved Taylor Momsen and Chace Crawford. Momsen portrayed Jenny Humphrey while Crawford took on the role of Nate Archibald. Their characters shared an innocent crush and flirtation during the early seasons of the show.

While fans speculated about a potential romance off-screen, Momsen later denied any serious relationship between the two actors. Although there were hints of a brief encounter, she confirmed that their connection was purely platonic and that they had a strong friendship developed through their time on set. In later interviews, Crawford hinted that he had engaged in flings with co-stars but didn't disclose who they were, leaving fans curious about the details.

Despite the ongoing speculation, the camaraderie among the cast persisted, and Crawford's affirmation about the downtime on set suggests that interactions among the cast were both expected and inevitable.

Kelly Rutherford and Matthew Settle: Close Friends or More?

Kelly Rutherford and Matthew Settle shared on-screen chemistry as Lily van der Woodsen and Rufus Humphrey. Their characters had a significant romantic storyline throughout the series, leading many to wonder if there was more to their relationship behind the scenes. Fans fueled the romance rumor mill after both stars went through personal relationship struggles around the same time.

While they never officially dated, their friendship remained a source of curiosity among fans. Settle and Rutherford occasionally shared social media posts and friendly interactions, leading to speculation that their relationship might be more than just platonic. The duo chose to remain private regarding their bond, leaving many to wonder what might transpire away from the public eye.

Despite the uncertainty, they remained durable friends, showcasing the supportive relationships forged on set during those formative years of their careers. The close-knit bonds among the cast have persisted, even many years after the show wrapped up.

As we reminisce about 'Gossip Girl' and its unforgettable cast, it’s clear that the drama on-screen was merely a slice of the exciting lives these actors lived off-screen. From whirlwind romances to enduring friendships, their stories continue to captivate audiences, demonstrating that sometimes real life can be more dramatic than fiction.

Blake Lively and Penn Badgley

Blake Lively and Penn Badgley, who played Serena van der Woodsen and Dan Humphrey, captured the hearts of many fans with their on-screen romance. However, the chemistry was not just limited to the fictional world of Gossip Girl, as the pair dated in real life during the show's early seasons. Their relationship blossomed just as the series began airing in 2007, creating a fervor among viewers who adored watching their love story unfold on and off screen.

Badgley later reflected on the significance of their relationship, stating that it provided a vital support system amid the overwhelming fame they experienced as young actors. He emphasized how their connection kept him grounded and helped him navigate the challenges of sudden stardom, particularly how he managed to stray away from potential pitfalls. Despite their split in 2010, both actors maintained a professional demeanor on set, proving their resilience as they continued to portray one of television's most beloved couples.

After Lively and Badgley's breakup, Lively went on to marry Ryan Reynolds in 2012, and the couple now shares four children. Meanwhile, Badgley found lasting love with Domino Kirke, whom he married in 2017. Their journey emphasizes the evolving nature of relationships and the impact of the entertainment industry on personal connections.

Leighton Meester and Sebastian Stan

Another compelling real-life romance from the Gossip Girl set involved Leighton Meester and Sebastian Stan. Their characters, Blair Waldorf and Carter Baizen, had an on-again, off-again relationship, which mirrored their off-screen romance that began around 2008. Initially, the two kept their relationship under wraps, but eventually, it became public when they were spotted together at various events.

Meester and Stan enjoyed a passionate connection during the height of Gossip Girl's popularity, but like many young relationships, it ultimately faced challenges. They broke up in 2010, and both actors have since reflected on the relationship and the lessons they learned. For Stan, filming the series marked a time of genuine connection and first love, a sentiment he continues to cherish.

Meester later married Adam Brody in 2014, and they welcomed two children together. While Stan has pursued various successful projects, he often looks back fondly on his time with Meester, recognizing how their shared experiences contributed to their personal growth.

Ed Westwick and Jessica Szohr

Ed Westwick and Jessica Szohr, known for their roles as Chuck Bass and Vanessa Abrams respectively, also experienced a romantic relationship that intrigued fans. Their on-screen chemistry spilled over into real life when they started dating in 2008. Keeping their romance relatively low-key at first allowed them to explore their relationship away from the public eye, though the media would soon catch wind of their chemistry.

As their relationship progressed, they faced the scrutiny that comes with being public figures, particularly when they decided to attend events together. Their on-again, off-again relationship was widely discussed and, like many couples in the spotlight, had its fair share of ups and downs. Ultimately, they decided to end their relationship in 2010, but both have since moved on to other significant partners.

Szohr, now a mother, has settled into her new role while Westwick recently married in 2024, showcasing their successes since parting ways. Their path reflects the complex dynamics of young love in a fast-paced industry.

Taylor Momsen and Chace Crawford

The younger cast members of Gossip Girl, Taylor Momsen and Chace Crawford, brought their own unique stories to the show's dating history. Momsen played Jenny Humphrey while Crawford portrayed Nate Archibald. Although their characters had romantic moments on the show, Momsen has consistently denied any serious romantic relations with Crawford during filming. She humorously addressed rumors of their rumored hook-up, emphasizing the strong friendships among the cast.

However, Crawford, during a revelation in 2024, admitted to having casual relationships with one of his co-stars, leaving fans speculating and eager to piece together the mystery. The dynamics among the cast members presented a unique social atmosphere where friendships could easily transition into something more. Despite these rumors, both actors have prioritized their careers and navigated the complexities of young adulthood.

Momsen and Crawford's experiences underscore the importance of friendship in Hollywood as they continue to support each other and the rest of their former cast members, reflecting the close-knit environment Gossip Girl fostered.

Kelly Rutherford and Matthew Settle

Perhaps one of the most talked-about relationships among the fans was the rumored romance between Kelly Rutherford and Matthew Settle, who played Lily van der Woodsen and Rufus Humphrey, respectively. Their characters often shared heartfelt moments throughout the series, which led to widespread speculation about a potential relationship off-screen.

During 2010, as both actors navigated personal challenges in their lives, the whispers of a romance grew louder. Rutherford and Settle were often seen together, igniting curiosity and excitement among fans. However, Settle was quick to dismiss the idea that they were anything more than close friends, despite the palpable chemistry.

Over the years, both have continued their professional journeys while occasionally being spotted together, sparking fresh rumors with each appearance. Their enduring friendship demonstrates how some connections can transform, showcasing the deeper relationships that can blossom in the entertainment industry.

Conclusion: The Legacy of Gossip Girl's Relationships

The intricate web of relationships among the cast of Gossip Girl not only entertained audiences but also provided a glimpse into the real lives of actors who experienced love in various forms. From high-profile pairings like Blake Lively and Penn Badgley to the deeper character explorations between Leighton Meester and Sebastian Stan, each couple contributed to the show's charm and allure.

As fan engagement continues to thrive even after the series concluded, the fond memories of these relationships linger on, leaving a lasting legacy. Each actor's journey reflects the emotional highs and lows experienced by many, reminding viewers of the timeless nature of love and friendship in a world filled with drama.

Gossip Girl remains a cultural phenomenon, and the real-life romances of its beloved cast members play an integral role in that legacy. With new generations discovering the series, these stories will continue to inspire discussions of love and connection among fans young and old alike.