Ranking Nate's Girlfriends on Gossip Girl: From Least to Most Desirable

Article Overview

Nate Archibald had a series of ill-advised relationships, often making questionable choices and getting caught up in complicated dynamics.

Nate had many girlfriends with hidden agendas or inappropriate connections, which made them unsuitable matches for him. Amongst all the chaos and unpredictable moments, Blair Waldorf stood out as one of Nate's finest girlfriends, as she genuinely accepted him for who he truly was.

When audiences first met Nate Archibald (Chace Crawford) on Gossip Girl, he was far from the ideal boyfriend. Despite being Chuck Bass' (Ed Westwick) best friend and Blair Waldorf's (Leighton Meester) boyfriend, Nate was involved with Blair's best friend Serena (Blake Lively). Though he was highly popular in high school, Nate still had a lot to learn about relationships. Nevertheless, he went on to date numerous characters on the show.

Nate often jumped into ill-advised relationships and his feelings seemed to change frequently. Unlike other Gossip Girl characters stuck in repetitive love triangles, Nate was known for exploring different love interests throughout the series. While he remained single by the end of the show, he had several romantic encounters along the way. While many of Nate Archibald's girlfriends were compelling characters in their own right, they ultimately weren't the right fit for him.

11. Catherine Beaton

Played by Madchen Amick

Catherine Beaton emerged as Nate Archibald's most problematic girlfriend. In the second season, he engaged in an affair with a married woman, which garnered widespread disapproval. Furthermore, when Nate's family faced financial difficulties, Catherine resorted to paying him to maintain their relationship, a morally dubious arrangement that doomed their union. The glaring power imbalance between them only heightened the potential for a catastrophic outcome.

Compounding matters, Catherine stooped to the shocking depths of engaging in a relationship with her own stepson, sparking a scandal that was wholly inappropriate. It is perplexing that Nate, typically known for making sound judgments, would choose someone as unsuitable as Catherine. This ill-fated relationship seemed uncharacteristic of Nate's typically rational decision-making approach.

10. Juliet Sharp

Played by Katie Cassidy

Gossip Girl may have conveniently forgotten about Juliet Sharp's storyline, but she definitely left a lasting impression on Nate's life during their time together as fellow Columbia students. Regrettably, Juliet's true intentions revolved around using Nate as a pawn to get closer to Serena, which was far from an ideal situation. Consequently, much of what Nate believed and knew about Juliet turned out to be nothing more than an illusion.

There were always trust issues in their relationship, and with good reason: Juliet consistently misrepresented herself and concealed her true intentions. Nate ended their relationship when things became too convoluted and subsequently assisted his friends in expelling her from the city. This illustrates the extent of Juliet's unsuitability as a girlfriend for Nate.

9. Diana Payne

Played by Elizabeth Hurley

Nate and Diana's encounter at a memorable Hollywood party was no mere coincidence, and much like Nate's previous girlfriends, Diana had hidden intentions. Their relationship was filled with excitement until they intertwined professional matters with personal pleasures, leading to a downward spiral.

Their affair was kept under wraps, but Diana grew envious when Nate showed friendliness towards other women. To Nate's dismay, it came to light that Diana had been hired by his grandfather to assist him in finding a job and launching a proper career. Having already been through a previous relationship with an older woman who exchanged money for companionship, this revelation brought a swift deterioration to Nate and Diana's relationship.

8. Bree Buckley

Played by JoAnna Garcia Swisher

Nate and Bree Buckley, daughter of his grandfather's political adversary, ignited a fiery conflict. For Nate, this decision was a deliberate attempt to defy his family's expectations. Both Nate and Bree yearned for individuality, disregarding the fact that their relationship would further fuel the rivalry between their families.

Yet once again, Bree harbored feelings for Nate, yet her ulterior motive was entirely different. Her true desire was to establish a connection with Carter Baizen (Sebastian Stan), who had inflicted harm upon her family. Bree employed Nate as a means to achieve her goal. Bree's foremost allegiance always resided with her family, never with Nate. This meant their relationship was destined for failure, regardless of any shared interests they may have had.

7. Sage Spence

Played by Sofia Black-D'Elia

Nate and Sage crossed paths when she interviewed him for an alleged article. However, it turned out that Sage was still in high school, only seventeen, and happened to be dating Serena's boyfriend. Considering Sage's young age and destructive nature, she was not a suitable partner for someone like Nate. At this point in the show, it seemed that Nate had learned his lesson about dating women who merely sought to harm those around them.

Despite a brief reunion after Sage caused a scandalous sex tape incident, their relationship was likely short-lived due to their significant incompatibility. Furthermore, Nate's relationship with Sage would likely face significant scrutiny if it occurred in present times, as their age difference was just as significant as the one between Nate and his much older girlfriends.

6. Jenny Humphrey

Played by Taylor Momsen

Jenny and Nate frequently crossed paths in the early stages of the show due to Jenny's desire to be part of the popular crowd and her eventual feud with Blair. Unlike everyone else who saw her as just another victim of the Upper East Side, Nate was one of the few popular kids who genuinely cared about Jenny's well-being. Despite having real potential, Jenny and Nate couldn't make it work as a couple.

Something always stood in the way of these two, whether it was Dan's decision to kick Nate out or Nate's growing affection for Serena. Although they both longed for a sense of normality amidst the chaos created by their peers, they ended up following divergent paths in life. Jenny's tendency for cattiness overwhelmed her, leading her to lose a potential great partner as a result of her deceitful behavior. Similarly, Nate ultimately chose to continue the family legacy by becoming a prominent public figure representing the Archibalds in politics.

5. Lola Rhodes

Played by Ella Rae Peck

Nate and Lola embodied the classic rich boy, poor girl trope, despite Lola being unaware of her immense inherited wealth. They shared a genuine connection and chemistry, with Lola showing no interest in exploiting Nate for his money or connections. Out of all of Nate's girlfriends, Lola was the most grounded and down-to-earth. She could have been a perfect match for Nate, as she often distanced herself from the unruly behavior of his friends.

Even though Lola joined in on the group's various schemes, she ultimately decided to leave at the end of season 5 when she landed a role in a movie. Their relationship may not have provided the extravagant drama that Gossip Girl fans craved, but it was undeniably healthier compared to Nate's other relationships.

4. Blair Waldorf

Played by Leighton Meester

At the start of the series, Nate and Blair were considered the ultimate couple. However, Nate had a secret: he had slept with Blair's best friend Serena the year before. Despite this, Blair still loved him and chose to forgive him. Their relationship became an on and off affair because they were comforted by their familiarity. As time went on, their love morphed into a deep friendship and their chemistry waned. Nevertheless, Blair will always be remembered as one of Nate's greatest loves because she accepted him for who he truly was.

The trouble with Nate and Blair was that they were the type of couple who would have become a society couple, establishing an Upper East Side empire, if they had continued their relationship solely out of comfort rather than genuine desire to build a life together. It's probable that they would have eventually treated each other more like business colleagues or allies in society rather than loving partners had they stayed together. Therefore, it's fortunate that they chose separate paths and maintained a friendship instead.

3. Raina Thorpe

Played by Tika Sumpter

Nate initially spent time with Raina as a favor to Chuck, who wanted to monitor the activities of Raina's businessman father. However, Nate and Raina developed a romantic connection and began dating. Despite Chuck's interference, Nate continued to support Raina in her quest to find her mother. Despite numerous obstacles presented by Chuck, Raina and Nate managed to maintain a strong bond.

Nate and Raina had a deep connection as they both experienced their own share of family drama. Coming from high-profile families and searching for their own place within them, they understood each other well. Their breakup was not a big spectacle either. Raina left a lasting impact on Nate, making them a good choice to revisit if there is ever a revival of the original characters.

2. Serena Van Der Woodsen

Played by Blake Lively

Serena and Nate's relationship was bound to happen given Nate's longstanding infatuation with her. As they matured, their childhood affection evolved into a deep and passionate love. Nate's devotion to Serena was unwavering; he would have gone to great lengths to make her happy. Nonetheless, Serena remains a controversial figure in Nate Archibald's romantic history as their initial attraction led to Nate's betrayal of Blair.

Their lack of effective communication ultimately led to the downfall of their relationship, as they continually assumed the worst about each other. If they had devoted more attention to improving this aspect of their connection, Nate and Serena could have been destined for each other. Both hailed as the Golden Boy and Golden Girl of the UES, they shared similar perspectives on life and harbored deep mutual trust. However, Serena's indecisiveness between Dan and Nate also played a detrimental role in their relationship. Ultimately, Serena's heart belonged to Dan, rendering her unable to fully commit to anyone else.

1. Vanessa Abrams

Played by Jessica Szohr

In season 1, Nate and Vanessa enjoyed a brief but meaningful relationship, characterized by an instant connection and undeniable chemistry that fans immediately noticed. Their time together was filled with playfulness, love, and a sense of normalcy. Unlike Nate's complicated friendships, their bond allowed them to genuinely have fun without being weighed down by outside factors. Unfortunately, the social dynamics of Manhattan inevitably created obstacles for Vanessa and anyone she tried to date on the show.

Vanessa and Nate could have been a perfect match if they had been able to overcome their issues with each other's friends. Vanessa had a positive effect on Nate, helping him become more socially conscious. Likewise, Nate could have been a positive influence on Vanessa, helping her resist getting caught up in Juliet's manipulations. Out of all of Nate's girlfriends in Gossip Girl, Vanessa Abrams was the ideal partner for him if only they had worked on their relationship.

Editor's P/S

As a Gen Z fan, I have mixed feelings about Nate's romantic journey in Gossip Girl. On the one hand, I understand that he was young and trying to figure out what he wanted in a relationship. On the other hand, I think he made some pretty questionable choices.

I think Nate's relationship with Blair was the most interesting and complex. They had a lot of chemistry, and they clearly cared for each other. However, they were also both very stubborn and proud, which often led to conflict. I think they could have been great together if they had been able to work through their issues.

I was also a fan of Nate's relationship with Serena. They were a lot of fun together, and they seemed to bring out the best in each other. However, I think they were ultimately too different to make it work long-term.

Overall, I think Nate's romantic journey was a bit of a mess. He made some good choices and some bad choices, but I think he ultimately learned from his mistakes. I'm glad that he ended up single at the end of the series. I think it was the best thing for him.