The Ultimate Ranking of Serena's Hottest Boyfriends on Gossip Girl

Summary

Serena's love life on Gossip Girl was complicated and exciting, with a wide variety of partners from different backgrounds and circumstances.

Serena's past relationships with Tripp, Gabriel, Max, and Ben were characterized by manipulation and deceit, causing her immense pain and feelings of betrayal. However, despite their tumultuous history, Serena's on-again-off-again romance with Dan played a significant role throughout the series. Surprisingly, in the finale, they ultimately ended up together, even though it was revealed that Dan was the infamous Gossip Girl.

Serena van der Woodsen, the iconic character from Gossip Girl, had a dating history filled with excitement and complexity. After her breakup with Dan in season 1, she embarked on a journey of dating a wide range of men, including childhood friends, former teachers, con artists, politicians, and even Dan (once again).

While Serena navigated through the world of privilege and tradition, her love life became a central aspect of her story on the show. Similar to other teenagers in the Upper East Side, she constantly had a changing lineup of partners and enjoyed exploring different connections. Interestingly, Serena's significant others were not restricted to her close social circle. She met people during her travels and encountered characters who appeared briefly before moving on from her life.

10 Tripp Vanderbilt

Serena and Tripp developed a mutual attraction during her involvement in his campaign, despite the unfortunate hurdle of his marriage. Tripp attempted to maintain Serena as a mistress while remaining married to the Vanderbilts, but she adamantly refused to partake in such deception.

Regrettably, Tripp proved to be a deceitful and manipulative companion, concealing his actions from Serena and orchestrating secret arrangements with his wife. Ultimately, he callously deserted her in a car accident, prioritizing his reputation over her safety. Tripp demonstrated a complete lack of empathy, leaving Serena rightfully deserving of someone far superior.

9 Gabriel Edwards

Armie Hammer's role as one of Serena van der Woodsen's boyfriends in Gossip Girl may have slipped the minds of some fans. While vacationing with her friend Poppy, Serena experienced heartbreak when Poppy's boyfriend, Gabriel, abandoned her friend for Serena and followed her to New York. Naive and captivated by the allure of European vacations and immediate romance, Serena failed to recognize the warning signs.

Tragically, the entire relationship unfolded as an elaborate scheme, with Poppy Lifton being complicit from the beginning. Initially intending to exploit Serena's affluent connections for financial gain, the situation grew increasingly complicated. Although Gabriel appeared to develop genuine affection for Serena, his questionable character ultimately proved too shady. This betrayal was exceptionally crushing for Serena, whose innate trust made the deception all the more devastating.

8 Aaron Rose

In season 2, Serena began seeing Aaron Rose as a way to pass the time. He was a pretentious artist who photographed attractive women but had difficulty committing to a monogamous relationship. This greatly differed from Serena's approach to dating. While she had been with multiple partners in the past, it was no longer what she desired.

The only emotion he displayed was slight annoyance when Serena assumed they were exclusive before he made that decision. The relationship held little significance, as Serena only used him as leverage to convince Dan to confess his love for her.

7 Max Harding

In Season 5, Ivy assumed the identity of Charlie Rhodes, only to be pursued and manipulated by her resentful boyfriend upon his return to New York. Max initially appeared kind-hearted, but quickly turned vindictive, following the pattern of Serena van der Woodsen's former partners who were introduced to the Upper East Side's dark side. It became evident that his motives revolved around infiltrating the affluent UES community, and like others before him, he exploited Serena as a means to an end.

Their relationship was short-lived, ending abruptly when Ivy orchestrated a deception, falsely labeling Max as a dishonest person. Some believed that Serena's trusting nature contributed to her unawareness, but it was Max who took advantage of her vulnerability, resorting to blackmail in his pursuit of Ivy. This manipulative behavior cast Max in an unfavorable light, highlighting the dangers inherent in Serena's romantic pursuits within her social circle.

6 Ben Donovan

Ben was Serena's teacher during her time as a boarding school student. Despite having feelings for each other, they never pursued a romantic relationship. However, things took a dark turn when Lily, Serena's mother, falsely accused Ben of statutory rape. This eventually backfired on Lily when Ben and his sister Juliet planned to sabotage Serena's life.

After Ben's release, he and Serena entered into a legal relationship. Unfortunately, there was no opportunity to address the unsettling beginnings, the emotional trauma resulting from false accusations and imprisonment, or the manipulation by his sister. Their time together was brief, as it became evident that their complicated relationship had no future. Ben served as both a supporter and a threat to Serena during his involvement in the show.

5 Dan Humphrey

Dan Humphrey holds the distinction of being Serena van der Woodsen's most famous boyfriend, as their on-and-off relationship played a significant role throughout their time in Gossip Girl. Although Dan and Serena started dating early on in season 1, their romance was often complicated by factors such as Georgina's involvement, their differing social statuses, and the revelation of them sharing half-siblings. Dan struggled to accept certain aspects of Serena's personality, causing fans to sympathize with her.

Despite their challenges, Dan and Serena's love endured, even amidst Dan's strong feelings for Serena's best friend Blair. While he could be affectionate and supportive, his bouts of jealousy and wavering loyalty posed difficulties. Nevertheless, it was evident that they were destined for one another. Despite Dan's shocking reveal as Gossip Girl and his torment of Serena for a significant portion of six years, she claimed to comprehend him and forgave him, ultimately reuniting with him in the finale.

4 Colin Forrester

Serena and Colin Forrester's connection was immediate, despite the complication of him being her professor. Colin even went so far as to leave his role as a guest lecturer to be with her, showing genuine interest and support. However, their timing was unfortunate, and they ultimately broke up due to Serena's inability to choose between Dan and Nate. Colin became a mere distraction in Serena's life, causing their romance to fade quickly, making him a forgettable figure among her significant others.

3 Steven Spence

Serena's role as the main character had become overwhelming. Fleeing Manhattan, she crossed paths with Steven. Adopting a different persona, she concealed her true identity. Yet, Steven, wise beyond his years, recognized Serena's inner struggles and embraced her completely, despite the initial deception.

Tragically, the Upper East Side and Steven's teenage daughter, Sage, conspired against the couple. Sage relentlessly attempted to undermine Serena, culminating in the release of a scandalous sex tape. Despite his genuine desire to be with Serena, Steven, a respectable man, succumbed to the mounting drama and ended their relationship.

2 Nate Archibald

Nate and Serena appeared destined to be together at the start of Gossip Girl, but their love turned out to be nothing more than a teenage fantasy. Despite Nate's longtime infatuation with Serena, their bond solidified as they navigated the fallout from her involvement with his cousin Tripp and the aftermath of a tragic accident. Nate seemed like the perfect partner for Serena van der Woodsen, but fate had other plans in store.

Nate possessed a kind-hearted spirit and always had Serena's best interests at heart. His focus remained unwavering, even in the face of distractions like Jenny. However, Serena left him behind when he reported William to the police for fabricating her cancer diagnosis. Although Nate's intentions were noble, his actions ultimately hindered their relationship. Sadly, Serena's growing affection for Dan ultimately marked the end of her and Nate's romantic connection.

1 Carter Baizen

Serena and Carter were remarkably compatible, both sharing scandalous pasts and a lack of trustworthiness. However, they were determined to prove themselves as better individuals than they were perceived to be. When Serena faced difficulties with her father and sought answers, Carter was there for her, offering the emotional support that nobody else had ever shown her.

Carter proved himself to be a valuable partner due to his immense self-awareness. He never caused harm to Serena and consistently made efforts to uplift her spirits during challenging times. If not for the haunting return of his past, he could have potentially been the ideal partner for Serena, enabling them to conquer Gossip Girl together.