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. Here are his relationships, ranked from worst to best.
11 Catherine Beaton
Nate has an affair with an adult married woman named Catherine Beaton in season two. When his family runs into financial troubles, she pays him to continue seeing her, which is not technically legal and a terrible premise for a relationship. The power differential between them is a recipe for disaster.
When Vanessa reveals that Catherine is also sleeping with her stepson, she leaves New York to avoid the scandal. This relationship was just completely inappropriate.
10 Sage Spence
Nate meets Sage when she profiles him for what he thinks is an article, but is actually a high school report. He finds out that not only is she in high school and seventeen, but she's the daughter of Serena's boyfriend, it's just not a great situation.
He breaks up with her when she releases Dan and Serena's sex tape, but she later manages to convince him to take her back. In the time jump at the end of season six, it doesn't look like they're still together.
9 Juliet Sharp
Nate wins the award for Used By the Most Women. Juliet Sharp is a fellow student at Columbia University, and they develop a friendship that turns into a romantic relationship once he realizes he doesn't want to be with Serena anymore.
There's always trust issues in their relationship, and with good reason: Juliet is constantly lying about who she is and what her motives are. He breaks up when things get too complicated, and later helps chase her out of the city when it's revealed that she only came to ruin Serena's life.
8 Diana Payne
Nate and Diana meet at a Hollywood party at the start of season five, where they hook up after he pretends her house is his. When she arrives in New York, they continue their relationship, and she hires him to work for her newspaper, The Spectator.
Their relationship is secretive because Diana doesn't want to take things public. Nate uses Charlie (who's really Ivy, but he didn't know that yet) to make Diana jealous so that she'll take things public with him. He later finds out that she was paid by his grandfather to give him a job and get him started by having him take over The Spectator.
7 Jenny Humphrey
Nate and Jenny develop feelings for each other when he moves in with her family in season two after Dan generously takes him in.
They don't really get to have a real relationship, because Dan kicks him out of the house when he finds out. Nate leaves a letter for Jenny, which Vanessa gets rid of. Jenny later tries to break up Nate's relationship with Serena, but still, nothing actually transpires between them.
6 Bree Buckley
Nate starts dating 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.
It's eventually revealed that Bree was only dating Nate in order to get to Carter Baizen, who she sought revenge for after he left her cousin at the alter. It's unclear why dating Nate was the only way she thought she could do this, but when the truth came out, Nate dumped her and she left town.
5 Lola Rhodes
Nate meets Lola when she's catering at Blair's wedding to Louis. He, Chuck, and Serena hitch a ride with Lola when they're trying to find Blair after she flees her reception. He's smitten with Lola, but she resists his advances, claiming that she isn't interested in someone like him.
He keeps asking though and the two start dating. She joins in on his group's various schemes but leaves at the end of season five when she gets cast in a role for a movie that will be shot in L.A. This relationship was pretty forgettable.
4 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. He comes clean when Serena returns to the Upper East Side, and Blair chooses to forgive him. He continues to harbor feelings for Serena, leading Blair to end things.
Nate later regrets the breakup, and the two briefly reconcile before Nate finds out that Blair slept with his best friend, Chuck. During their senior year, the two begin seeing each other again, but soon realize that they had only gravitated toward one another again because of the comfort in familiarity. All in all, they just weren't a good match.
3 Serena Van Der Woodsen
Nate had always had a thing for Serena, and Serena dates everyone, so it was inevitable that they would date each other eventually. Nate wins her over after his cousin leaves her at the sight of a car accident. Things start to go wrong when Jenny gets involved, and when Serena is secretive about her communications with her ex, Carter Baizen.
Nate doesn't want to be with Jenny, and Serena is only talking to Carter to find her father, but their communication skills are pretty poor so they each assume the worst. Things are strained even further when Nate calls the police on Serena's father, causing him to flee New York. Once Serena kisses Dan, she realizes that she needs to be on her own until she figures out what she wants, and the two break up.
2 Vanessa Abrams
Nate and Vanessa date briefly in season one, until the drama in Nate's family forces him to reevaluate whether he has the energy to focus on a relationship. At the start of senior year, the two reconnect, but Nate is seeing an older, married woman, who blackmails them both to keep them apart.
Later, Vanessa comes to Nate's aid with a family matter, leading them to reconnect. Once Vanessa gets to know his family of WASP-y politicians, she begins to realize that they may not be able to have a future together. She's further bothered by the friendship he has with his ex, Blair, and the two break up for good.
1 Raina Thorpe
Nate hangs out with Raina as a favor to Chuck, but they hit it off and start dating. Nate supports Raina in her search for her mother, but Chuck continues to get in the way. Raina asks Nate to make a choice between the two of them, and Nate chooses her when Chuck starts to spiral out of control.
Nate actually goes through a lot with Raina and tries to help her through all of her family drama, something he understands quite well. Their breakup isn't anything dramatic, but due to Raina moving to Chicago at the end of season four.
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February 03, 2021 at 02:30AM
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