However, they just weren't meant to be considering their history with one another's best friends. Their relationship definitely left fans wondering how Dan could even consider being with Blair knowing she was Nate's first love. At the least, this would have added a pretty awkward element to Nate and Dan's friendship. Even though Dan made his fair share of mistakes, he was still Nate's least problematic friend.
Dan was always the pal that Nate could go to whenever he wanted to talk and escape the pressures of the Upper East Side. Dan was always there for him but the same can't really be said for Nate. Nate was often too concerned with his own drama and didn't really go out of his way to check on Dan. Don't get us wrong, Lonely Boy wasn't an angel by any means, but he still deserved a friend who would support him through it all and he never really had that.
While it's not entirely surprising that Dan didn't come clean to anyone about his secret blogging gig until the very end, it's still strange that he was able to keep such a huge secret from his close friends.
Dan shared in the finale that Jenny was the only one who knew his secret and that just doesn't add up. After everything the gang had been through together, it would have made sense if Dan confided in Nate about his Gossip Girl secret, but maybe he figured he was in too deep.
By Bethany Aroutunian Published Jan 24, Share Share Tweet Email 0. She worries that he will be pushed into the van der Bilt machine and come out like Tripp, a serious politician focused on status.
After she breaks down, Nate comforts her and the two begin to grow close again. Nate then renews his relationship with Blair and they become a couple again Remains of the J. Meanwhile, Blair makes a deal with William to be a bridesmaid and to be accepted to the Junior Whitney Committee if she convinces Nate to go to Yale. Before the rehearsal dinner, Nate learns that William was the one who had Howard arrested and investigated by the FBI.
He tells everyone at the dinner during his best man's speech, and William admits he did it, but that he confronted Howard first to ask him to stop. He also tells Nate about his deal with Blair, which causes Nate to question his decision to trust her.
They make up, but Nate is still worried about losing her due to her closeness to Chuck. To prevent this, he buys an apartment for them to move in to after graduation but instead of spending the night in it with him, she chooses to go with Chuck to find Georgina Southern Gentlemen Prefer Blondes. When she returns, she tells Nate that she doesn't think they should move in together and they agree to go to prom together instead.
At prom, they're crowned King and Queen but they break up; feeling like their relationship should stay in high school. He goes to his first day at his internship only to discover his boss is interested in him, so he quits and decides to accompany Vanessa backpacking instead. The season starts with Nate returning to Manhattan with Bree Buckley , a member of a political rival family.
Wanting to show his family that he is his own person, he begins to date her Reversals of Fortune. While Bree and Nate's relationship grows, Blair senses something suspicious about her and thinks she is up to something.
Eventually, it is discovered that Bree wants to take down Carter Baizen, who is dating Serena, for leaving her cousin at the altar. Nate finds out, and even though Bree apologizes, he says it's not enough and breaks up with her Rufus Getting Married. Nate decides to tell Serena where Carter is, and offers to help her help Carter by settling his debt through a poker match with Bree's brothers. To get them to play Carter's debt, he offers to play a photo of Tripp at his bachelor party with a bong.
They lose, and PJ Buckley wins the photo. Serena later overhears Nate telling William that he used her to get back by betting a fake photo. Serena is so upset at being used to help Tripp's campaign for Congressman that she informs the Buckleys of Nate's trick and is rewarded by settling Carter's debt Enough About Eve. After several polls predict Tripp to lose the election, a man who appears to have fallen into the Hudson River is saved by Tripp, who is hailed as a hero.
However, when Vanessa later reviews her video footage, she realizes that the man who nearly drowned was paid off to give Tripp an edge in the last hours of the election. Vanessa confronts Nate about this fact and he is horrified at the thought. She admits that she is selling the footage to New York 1, a news network,, and Nate pleads with her to wait until after the election.
She tells him that it is unethical, but he accuses her of only wanting the fame of catching the story. Nate returns to the campaign office to confront his grandfather for setting up the scheme, but he denies any involvement.
Worried about the video's affect on the outcome of the election, Nate hires a person to pretend to be the woman buying the footage for New York to keep it out of the media. Vanessa ends up finding out about his betrayal, and the story is revealed on the news anyway.
Nate takes matters into his own hands and takes the blame for orchestrating the fake drowning, and Tripp ends up winning the election. After the election, Serena is hired by Tripp to work for his office as Congressman, and the two begin to develop feelings for each other They Shoot Humphreys, Don't They?
Nate tries to talk her out of these feelings, as Tripp is a married Congressman and has too much to lose, and volunteers to help her avoid him until he leaves for Washington D. While distracting her, he admits to her that he used to love her and tried to tell her, but told Jenny instead.
As they're about to kiss, Tripp interrupts them, having found out his wife Maureen had set up the Hudson drowning scheme, and seeks out Serena for comfort. In The Treasure of Serena Madre , Nate informs Maureen, who has suspicions about an affair, about Serena and Tripp's feelings for each other and steals a security tape from The Empire of Tripp and Serena kissing in the elevator.
Tripp decides to leave his wife, encouraging Serena to be with him. While leaving to go away with Tripp, Serena is caught by Nate who tells her how he feels. She once again leaves him heartbroken, choosing Tripp. They head to a house outside the city in The Debarted and hide out for awhile, until Tripp leaves for an afternoon; claiming he's meeting with William.
Serena becomes bored and calls Nate to see if he knows of anything she can do. While on the phone, Nate tells her that William is out of town and can't be meeting Tripp.
He's meeting with Maureen, who proposes that he can stay with Serena behind the scenes so long as they stay married in public. Maureen goes to the house and blackmails Serena into accepting with a letter from her father William van der Woodsen that she found at the VDW's. When Tripp returns, they head back to the city but end up in a major car accident.
Tripp flees the scene and Nate discovers the accident on his way to the house. At the hospital, Tripp tries to get in and see Serena but Nate punches him and tells him to leave.
After Nate saves Jenny after she is drugged The Empire Strikes Jack , she begins to develop feelings for him despite knowing he's with Serena. Meanwhile, Nate and Serena begin to experience problems, from miscommunication regarding the speed of their relationship, distrust over Serena lying about her adventures with Carter Baizen to find her dad The Unblairable Lightness of Being , and hiding her mother's illness.
Jenny attempts to sabotage the couple so she can be with Nate. They later end up reconciling, and leave their friendship on good terms. Things with Serena are tested again in Ex-Husbands and Wives when he calls the cops after discovering that William lied about her mother being sick.
He finds it in his heart to forgive her; however, Serena breaks up with him, saying that while she does love him, she needs a break from them. Nate, hurt, ends all connections to Serena, and tells Vanessa who is currently away in Haiti, doing an internship with CNN about what happened between her and Dan compromising their relationship, and ends the episode moving on from Serena. When the series resumes, it's revealed Nate spent the summer sleeping through Chuck's little black book to get over Serena.
Before he returns to college he meets Juliet Sharp , a fellow Columbia student who helps him realize that he still has feelings for Serena that makes him act reckless Belles de Jour.
When Serena returns to the city Double Identity and tries to resume her friendship with Nate, he realizes he's still angry at her and begins too fall for Juliet and they begin a relationship The Undergraduates. Their relationship goes smoothly until he begins to suspect that Juliet is hiding something from him and confronts her about it, but discovers she has a brother in prison. To make up for lying, she invites him to her apartment; but it's revealed she paid a doorman to let her use an apartment in the building for the night Touch of Eva.
Nate's father is transferred to Riker's Island Prison, where he is assaulted by Juliet's brother Ben Donovan as a way to send a message to Juliet about dating Nate. Feeling guilty, she breaks up with Nate to keep him and his family safe Easy J.
He makes a deal to leave New York forever if they never tell Raina. Knowing she is still planning nuclear revenge on Chuck, Nate tells her the truth, ruining the deal. After the ordeal, Nate and Raina break up, as she wants to return home to Chicago. Both single, Nate and Chuck decide to engage in a Lost Summer and travel the world together. After traveling together, Chuck and Nate end up in Los Angeles where Serena is working on a movie set.
Chuck is in a new, happier, state of mind after deciding to say yes to any opportunity given to him. He influences Serena and Nate to try it, and they all end up a little bit happier. Before a party, he gets into a motorcycle accident and becomes severely injured.
However, he is unable to feel it and doesn't even notice until he sees himself shirtless Yes, Then Zero. He has his mom's house doctor come over and look him over; and the doctor tells Nate to keep a close eye on Chuck as his injuries are bordering on dangerous Beauty and the Feast. Chuck begins seeing a therapist, and decides he wants to seduce her.
At the same time, Nate wants to find courage to be able to cross moral lines. After Nate meets Lola Rhodes and finds she has zero interest in him, so much so she refuses to work as a caterer at any of his office parties, Chuck offers to let him have a party at The Empire so she'll attend Crazy Cupid Love.
After Diana Payne reveals herself as Chuck's mother thanks to Lola accidentally live streaming it, Nate sides with Chuck and agrees to help him in any way possible to find the truth Salon of the Dead. He follows through with his promise and finds that Diana is not Chuck's real mother, and tells him as soon as he receives confirmation Despicable B. After Serena turns up missing, Nate and Chuck, along with Blair, team up to find her.
When they do, the find she is healthy, happy, and unwilling to return to the city Gone Maybe Gone. In order to save his newspaper, Nate commits fraud by faking the numbers to get a new credit line, and Bart, intent on destroying Chuck, finds out and uses it as blackmail. When Ivy steals the microfilms containing the records of his illegal oil dealings, Bart uses Nate to find out what Chuck's plan is Where the Vile Things Are. Angry at Nate, they briefly fight but get over it as they find a way to win.
After the records are burned by Lily, Nate tries to encourage Chuck to continue his war against Bart. Along with Blair, they obtain Bart's passwords and they reignite his motivation to fight back It's Really Complicated. After Nate becomes of little use to him and he finds out he is also helping Chuck, Bart has Nate arrested.
In the time jump, they're revealed to still be best friends. Money, the pleasures money brings me, and you. Did you get what you wanted like you do with all those other girls? What started as harmless high school fun, quickly warped into the most destructive friendship on Gossip Girl.
Not only was Georgina Sparks just plain mean, but she was also manipulative and scary. She understood Serena's thought process and knew exactly how to play mind games on her.
Serena was close to Georgina when she was young and in a phase of constant partying and drinking, but this toxic relationship paired with Serena's terrible judgment at the time only produced horrible situations for this pair. Dan never really fit into the world of Nate Archibald, but even in the early seasons when everyone else was so against Dan, there was a glimmer of positivity from Nate.
In those times when Nate shut out the world, somehow Dan could relate and help him out of whatever dark place Nate found himself in. They both could somehow relate to not completely fitting into the worlds they were thrown into, and they had each other to seek out in times of drama.
There wasn't anything necessarily terrible about this pair, but it just felt like they never fit together. Whether they were strictly friends or locked in a weird and secretive romance, this pairing felt forced. Deep down, they both knew they were truly too different to ever make anything work. It was good that they had their time together without Blair totally degrading Dan she barely ever called him by his first name but it kind of felt like two puzzles pieces that just did not go together.
The most iconic friendship in Gossip Girl history goes to these two. Serena and Blair had the type of friendship that people aspire to find.
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