Nate’s Girlfriends, Ranked From Worst To Best

When audiences were first introduced to Nate Archibald on Gossip Girl, he was far from an ideal boyfriend. Even so, he went on to date many characters on the show.

He often dove headfirst into ill-advised relationships, and his affections shifted depending seemingly on the day. He ended the series single, but had many romances throughout. These are all of his relationships, ranked from worst to best.

11/11 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.

10/11 Juliet Sharp

Juliet Sharp’s storyline was forgotten by Gossip Girl, but Nate’s fellow Columbia student made sure she left a mark in his life. Sadly, Juliet intended to use Nate to get closer to Serena, which was not ideal.

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

9/11 Diana Payne

Nate and Diana’s fateful Hollywood party meeting wasn’t a chance one, and like 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. She sure was twisted in her ways.

8/11 Bree Buckley

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.

Yet again, Bree had affections for Nate, but her endgame was something else completely. She wanted to get closer to Carter Baizen, who had wronged her family. Bree’s first priority was always going to be her family, and never Nate.

7/11 Sage Spence

Nate met Sage when she profiled him for what a supposed 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.

They did get back together after the 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.

6/11 Jenny Humphrey

Dan’s moment of generosity with Nate saw the beginning of feelings between Jenny and Nate, who 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. Jenny’s cattiness got the better of her, and she lost a potentially great partner because she tried to be underhanded in her ways.

5/11 Lola Rhodes

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 average chemistry, but at least Lola did not attempt to wrangle money or connections from Nate.

Lola even joined in on his group’s various schemes, but left at the end of season 5 when she got cast in a role for a movie. This relationship was pretty forgettable, but one of Nate’s healthier ones.

4/11 Blair Waldorf

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.

3/11 Raina Thorpe

Nate hung out with Raina as a favor to Chuck, but they hit it off and started dating. Nate supported Raina in her search for her mother, but Chuck 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. Their breakup wasn’t anything dramatic, but Raina left an indelible mark on him.

2/11 Serena Van Der Woodsen

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.

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 were 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 ship.

1/11 Vanessa Abrams

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, but the politics of Manhattan kept them apart.

Vanessa had her issues with Nate’s friends, which led to a breakup between the two, but they did have potential to be endgame. Possibly, Nate could have also kept her reined in so she wouldn’t get carried away with Juliet and company, since he was generally a calming entity. These two were a pretty great couple.

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