Summary

• Nate Archibald had a series of ill-advised relationships, often making questionable choices and getting caught up in complicated dynamics.
• Several of Nate's girlfriends had ulterior motives or inappropriate relationships, making them unsuitable partners for him.
• Despite the drama and ups and downs, Blair Waldorf was one of the best girlfriends Nate ever had, as she loved him for who he was.

When audiences were first introduced to Nate Archibald (Chace Crawford) on Gossip Girl, he was far from an ideal boyfriend. Nate was the best friend of Chuck Bass (Ed Westwick), the boyfriend of Blair Waldorf (Leighton Meester), but he also had a relationship with Blair's best friend Serena (Blake Lively). He might have been one of the most popular guys in high school, but he still had a lot to learn about relationships. Even so, he went on to date many characters on the show.

Nate often dove headfirst into ill-advised relationships, and his affections shifted depending seemingly on the day. Nate was one of the Gossip Girl characters known for exploring love instead of being caught in a love triangle with the same people for most of the series' run. He ended the series single but had many romances throughout. While plenty of Nate Archibald's girlfriends are great characters in their own right, they weren't right for him.

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11 Catherine Beaton

Played by Madchen Amick

The worst of Nate Archibald's girlfriends was Catherine Beaton. Nate had an affair with an adult married woman in season 2, and the world cringed. When his family ran into financial troubles, she paid him to continue seeing her, which was not technically legal and a terrible premise for a relationship. The power differential between them was a recipe for disaster.

Add to that the fact that Catherine was sleeping with her stepson, and scandal ensued. This relationship was completely inappropriate, and Catherine was a horrible choice for the surprisingly wise Nate. Of his friends, Nate usually made the most logical decisions, so this relationship seemed out of character for him.

10 Juliet Sharp

Played by Katie Cassidy

Juliet Sharp's storyline was forgotten by Gossip Girl, but Nate's fellow Columbia student made sure she left a mark on his life. Sadly, Juliet intended to use Nate to get closer to Serena, which was not ideal. Much of what Nate knew about Juliet wasn't real.

There were always trust issues in their relationship, and with good reason: Juliet was constantly lying about who she was and what her motives were. Nate broke up with her when things got too complicated and later helped his friends to chase her out of the city. That's how terrible a girlfriend Juliet was for Nate.

9 Diana Payne

Played by Elizabeth Hurley

Nate and Diana's fateful Hollywood party meeting wasn't a chance one, and like so many of Nate's other girlfriends, Diana had ulterior motives. Their relationship was quite exciting until they mixed business with pleasure, and it all went downhill after that.

Their relationship was secretive, but Diana got jealous as Nate started getting friendly with other girls. To his dismay, it was revealed that Diana was paid by his grandfather to give him a job and get him started with a real career. After already experiencing one relationship with an older woman who took money in exchange for being around him, the reveal made the relationship with Diana sour very quickly.

8 Bree Buckley

Played by JoAnna Garcia Swisher

Fireworks erupted between Nate and Bree Buckley, the daughter of his grandfather's political rival. This choice made sense for Nate, who always wanted to do something his family wouldn't approve of. Nate very badly wanted to stand out from his family, and Bree also seemed like she wanted to stand out from hers, not minding that she would be dating a family rival.

Yet again, Bree had affection for Nate, but her endgame was something else completely. She wanted to get closer to Carter Baizen (Sebastian Stan), who had wronged her family. Bree used Nate to do it. Bree's first priority was always going to be her family, and never Nate. That meant the two of them never would have worked no matter how much they might have had in common.

7 Sage Spence

Played by Sofia Black-D'Elia

Nate met Sage when she profiled him for what was supposedly an article, but she turned out to be in high school and seventeen, as well as the daughter of Serena's boyfriend. Sage was too young and too destructive to be a good partner to somebody like Nate. By this point in the show, Nate had appeared to learn his lesson in dating women who were only interested in lashing out at others around them.

They did get back together after a sex tape fiasco she caused, but it's likely their relationship didn't last very long, because they were highly incompatible. Also, this relationship of Nate's would never fly today. There was too much of an age difference between Nate and Sage, just like there was between Nate and his girlfriends who were so much older than him.

6 Jenny Humphrey

Played by Taylor Momsen

Jenny and Nate crossed paths frequently early in the show thanks to Jenny's desire to be part of the popular crowd and her eventual feud with Blair. Nate was one of the few popular kids who genuinely seemed to care about Jenny's well-being, while everyone treated her as just another casualty of the Upper East Side. Jenny and Nate had real potential but could never really make it as a couple.

Something always came in the way of these two, whether it was Dan kicking Nate out or Nate falling for Serena. The two of them could have really understood one another's desire for normalcy amid the shenanigans of their peers, but they ended up taking very different paths in life. Jenny's cattiness got the better of her, and she lost a potentially great partner because she tried to be underhanded in her ways. Nate also, ultimately, decided to carry on in the family business, becoming a very public and political face for the Archibalds.

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5 Lola Rhodes

Played by Ella Rae Peck

Nate and Lola followed a classic rich boy, poor girl trope, even though Lola was the heiress to a large fortune she did not know about. They were sweet and had some chemistry, and Lola did not attempt to wrangle money or connections from Nate. Of Nate Archibald's girlfriends in the series, Lola was actually the most down-to-earth. She could have been a good match for Nate since he so often wanted to avoid the antics of his friends.

Lola even joined in on his group's various schemes though. She was willing to help with their plans to be part of the group but left at the end of season 5 when she got cast in a role for a movie. This relationship might not have been full of the drama that Gossip Girl fans loved to watch, but was one of Nate's healthier ones.

4 Blair Waldorf

Played by Leighton Meester

Nate and Blair were the "it" couple at the beginning of the series, but he hadn't yet confessed to Blair that he had slept with her best friend Serena the year prior. Blair truly did love him, because she chose to accept him even after he came clean to her. They were on again and off again a few more times after that because they found comfort in their familiarity. Their love turned into fast friendship over the years, and the chemistry wasn't great. However, Blair was one of the best girlfriends Nate ever had because she loved him for who he was.

The trouble was that Nate and Blair were the kind of couple that would have ended up as a society couple building an Upper East Side empire if they had stayed together simply because they were comfortable, not because they genuinely wanted to build a life together. It's likely they would have eventually treated one another more like business colleagues or societal allies instead of loving partners if they had remained together, so it's good that they went their separate ways and stayed friends instead.

3 Raina Thorpe

Played by Tika Sumpter

Nate originally hung out with Raina as a favor to Chuck. Raina was the daughter of a businessman that Chuck wanted to keep an eye on. Raina and Nate, however, hit it off and started dating. Nate supported Raina in her search for her mother, but Chuck could never let them be. To their credit, Raina and Nate had a decent bond which survived many Chuck-sized hurdles.

Nate actually went through a lot with Raina and supported her through all of her family drama, which was something he understood well. The two, with high-profile families and searching for their own places within their families, understood one another well. Their breakup wasn't anything dramatic either, and Raina left an indelible mark on him, so if a revival ever revisited the original characters, Nate and Raina could be a good choice to revisit.

2 Serena Van Der Woodsen

Played by Blake Lively

Nate always had a thing for Serena, so it was inevitable that they would date each other eventually. Their childhood love blossomed into young love as they grew up, and Nate would have done anything for her. Serena, however, is one of Nate Archibald's most controversial girlfriends because their initial attraction to one another meant that Nate cheated on Blair.

Their communication skills were pretty poor, so they each assumed the worst about each other, which led to the demise of their relationship. If they had worked on this aspect, Nate and Serena could have been meant to be. They were the Golden Boy and Golden Girl of the UES, had similar views on life, and trusted each other deeply. Serena's indecision about Dan and Nate also hurt this relationship. Serena's heart ultimately belonging to Dan meant that she could never fully commit to anyone else.

1 Vanessa Abrams

Played by Jessica Szohr

Nate and Vanessa dated briefly in season 1, but they had instant chemistry and a great vibe which fans picked up on immediately. Life for Vanessa and Nate was actually playful, loving, and normal. The two of them had genuine fun together that didn't have to be bogged down by everything else going on with Nate's friends though. The politics of Manhattan kept them apart, much as it did for Vanessa and almost anyone else she attempted to date in the show.

Vanessa had her issues with Nate's friends, which led to a breakup between the two, but they did have the potential to be endgame if she and Nate had found a way to compromise. Vanessa was a good influence on Nate when it came to being more socially aware. Nate would have been a good influence on Vanessa when it came to her falling for Juliet's schemes too. These two were a pretty great couple, and of all of Nate Archibald's girlfriends, Vanessa Abrams would have been the best fit if they had worked on maintaining a relationship in Gossip Girl.

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  Gossip Girl

  Release Date:

  2021-07-08

  Cast:

  Jordan Alexander, Whitney Peak, Tavi Gevinson, Thomas Doherty, Emily Alyn Lind, Eli Brown

  Genres:

  Drama, Romance

  Rating:

  TV-14

  Seasons:

  2

  Writers:

  Joshua Safran

  Streaming Service(s):

  Max

  Showrunner:

  Joshua Safran

  Season List:

  Gossip Girl - Season 1, Gossip Girl - Season 2