|“||Look, Nathaniel, I care about three things. Money, the pleasures money brings me, and you.||”|
— Chuck to Nate, Dare Devil
Chuck and Nate, along with Serena and Blair, have a core friendship that predates the beginning of the series. Unlike the girls, Chuck and Nate have very little drama or moments of serious betrayal. With a few exceptions, they never purposefully betray or hurt each other and instead are known for being unconditionally supportive of one another.
Nate and Chuck are passing acquaintances, but attend different schools and are not friends.
The two begin the series as best friends (Pilot), and it's made clear that they have been best friends longer than either can remember. After hosting a Lost Weekend, Nate reconnects with Carter Baizen, and begins to wonder about life outside the Upper East Side. Chuck is uninterested, and encourages him to remember the pleasures of their lifestyle. Nate leaves the weekend after arguing with Chuck and ends up at a poker game with Carter only to discover Carter and his friends are working together to get money from him. Chuck arrives to save Nate and the two make up (Bad News Blair). After Nate and Blair break up (Victor Victrola), she begins hooking up with Chuck from time to time. Having realized he has feelings for her, he starts to scheme to keep Nate away from her. Before Cotillion, he convinces Nate that Carter is interested in her and he ends up hitting Carter at the ball. Afterwards, Blair realizes Chuck set them up and gets back together with Nate (Hi, Society). During the holidays, Nate goes to Monaco with Chuck (Roman Holiday). After school resumes, Chuck, Nate, and Blair attend a pool party at Constance Billard/St. Jude's where a kid almost dies. Chuck, still not wanting Blair with Nate, blackmails her with threatening to tell Nate she lost her virginity to him. As a result, Blair distances herself from Nate but eventually realizes Chuck is bluffing so she gets back with him fully.
In A Thin Line Between Chuck and Nate, Blair has a pregnancy scare and Serena, not knowing she slept with Nate, goes to Chuck for help. He informs her that she also slept with Nate. After Blair finds out she isn't pregnant, she rejects Chuck completely and as revenge, he tips off Gossip Girl that she slept with two guys in one week. When Nate hears the rumor, he assumes it's false until Jenny, who is angry at Blair, confirms it. Nate physically confronts Chuck, and orders him to stay away from him. He also breaks up with Blair. In Much 'I Do' About Nothing, Chuck spots Nate's dad Howard Archibald at Lily and Bart's wedding conducting a deal, despite being newly released from jail. Even though he's still fighting with Nate, he tells him anyway. After Nate realizes Chuck was telling the truth, they make up.
After finding out his family has no money, Nate begins sleeping with Catherine Beaton for money (Never Been Marcused). However, his mother Anne Archibald works out a deal with Chuck to borrow money; unbeknownst to Nate. He eventually finds out and while he is angry at first, gets over it. During a weekend college visit to Yale University, Chuck is kidnapped by a gentlemen's society who promise to let him join.. so long as he gives them Nate; who they hate because of his father's crimes. Not wanting Nate to be hurt, Chuck sets Dan up and tells them he is Nate. When Nate finds out, he distances himself from Chuck and begins to befriend Dan (New Haven Can Wait). After Nate moves in with the Humphrey's (Chuck In Real Life) and is eventually kicked out after kissing Jenny, he returns to his empty home briefly before heading out to the Hamptons to stay with his mom. While he's there, Chuck stops by and realizes how broke the Archibald's really are. He offers to help, but Nate rejects him and leaves (There Might be Blood).
On Thanksgiving in The Magnificent Archibalds, Nate and Anne arrive back in the city and meet with Howard, who asks them to come live in Dominica with him. At the same time, Vanessa is approached by a FBI agent who knows Howard is planning to hold both Anne and Nate for ransom to get money from the van der Bilt's. She informs Chuck, and the two eventually convince Nate to get his father to do the right thing and turn himself in. Afterwards, Chuck and Nate make up and become friends again. After Bart dies, Nate goes along with Chuck to the reading of the will for support (Gone with the Will). Meanwhile, Nate and Blair agree to get back together and he leaves Vanessa for her. Jealous of their relationship, both Chuck and Vanessa team up to separate them but their plan fails (Remains of the J). After awhile, Nate realizes Chuck has feelings for Blair and they begin to fight over her. In order to ensure he won't lose her, Nate buys an apartment to live in with Blair but rather than spend a night in it with him, she heads out of town with Chuck to track down Georgina (Southern Gentlemen Prefer Blondes). While in the middle of a scheme, Blair asks Chuck one last time if his feelings for her are real and Chuck, afraid of being unable to make her happy, encourages her to be with Nate (The Wrath of Con). Before prom, Chuck sabotages all of Nate's plans and replaces them with the plans Blair made in her "Prom Scrapbook" as a kid. At prom, Blair and Nate win Prom King and Queen but break up due to their relationship feeling too high school (Valley Girls). After graduation, Chuck finally reveals his true feelings to Blair and they enter into a relationship (The Goodbye Gossip Girl).
After Chuck purchases The Empire Hotel (The Lost Boy), he invites Nate to sleep over whenever he wants. When Nate's cousin Tripp van der Bilt runs for Congress, Chuck lets them use the hotel as the headquarters on Election Night (The Grandfather: Part II). After awhile, Nate moves into Chuck's penthouse with him (They Shoot Humphreys, Don't They?). After Nate is rejected by Serena for Tripp, Chuck cancels his plans to spend Thanksgiving in Paris with Blair to stay home and get drunk together (The Treasure of Serena Madre).
After losing his hotel to Jack Bass and trying to sell Blair in order to get it back (Inglourious Bassterds), Chuck and Blair remain estranged. In The Unblairable Lightness of Being, Blair tells Nate what Chuck did to get his hotel back. Nate is shocked, and becomes angry at Chuck. However, they don't fight for long and in an effort to help him get over his anger at Serena for leaving town silently, Chuck invites Nate to attend an art party in Brooklyn with Jenny. Unbeknownst to Nate, Chuck, feeling he has lost his best friend to Serena, has teamed up with Jenny, who is interested in Nate, to split them up. However, their plan fails when Serena returns before Jenny can kiss Nate (Dr. Estrangeloved). In the season finale Last Tango, Then Paris, Nate and Serena break up and to help him ease the pain, Chuck leaves Nate his "Little Black Book" to get all his desires out.
Chuck and Nate continue living together in the fourth season. When Chuck returns home with his new girlfriend Eva Coupeau, Nate comments to Chuck how he likes that he's a genuinely nice person now (Touch of Eva). After being released from prison, Howard moves into The Empire with Nate and Chuck while he's on parole (The Townie). Soon after, Howard takes a job with Bass family enemy Russell Thorpe (The Kids Are Not Alright). Nate finds out and plots with Chuck to ask Raina Thorpe, Chuck's new love interest and Russell's daughter, to have Howard fired. When Howard finds out, he moves out of The Empire and promises to help Russell with whatever he needs (Damien Darko). However, things are resolved as Howard helps Nate and Chuck figure out what exactly Russell is planning with Bass Industries; as well as giving them a step up to winning against him (It-Girl Happened One Night).
After Nate begins dating Raina (While You Weren't Sleeping), he agrees to help her search for her mother. Chuck, having just learned that Bart killed her mother, tells Nate to make her stop. After they strike out with meeting a woman, Chuck admits to Nate the real truth about who killed her mother (Petty in Pink). He tells Raina, who makes her choose between him and her. Nate ultimately chooses his friendship with Chuck and leaves. However, after Blair becomes engaged to Louis Grimaldi, Chuck becomes angry and smashes a glass window near Blair. Nate witnesses the scene, then calls Raina to tell her he made the wrong decision (The Princesses and the Frog). The next day in Shattered Bass, he prepares to leave The Empire and his friendship with Chuck behind, until he finds out Raina enlisted Chuck's uncle Jack to help her exact revenge on him. Nate teams up with Jack and Chuck to finally find the truth behind Avery Thorpe's murder and they discover Russell was the one responsible. 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. In The Wrong Goodbye, Nate, Chuck, and Raina save Blair after she is kidnapped by Russell. 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). After their return to New York, Dan finds Chuck paying some guys to beat him up and informs Nate. 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. They agree to help each other, Nate tells Chuck to pretend to be interested in her interest and Chuck tells Nate to tag along with Charlie Rhodes (Ivy Dickens) to find secrets (I Am Number Nine). In Riding in Town Cars With Boys, Nate helps Blair and Chuck escape to finally be together, and witnesses their horrific car accident.
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). After Dan screws up his deal with Nate (Dirty Rotten Scandals), and writes a brutalizing article on Chuck, Nate sides with Chuck and alienates Dan from his life (Monstrous Ball). 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. However, Nate is released thanks to Chuck leaving for Russia at Bart's request (The Revengers).
In the series finale New York, I Love You XOXO, Nate is present while Chuck and Blair marry. In the time jump, they're revealed to still be best friends.
"Look, Nathaniel, I care about three things. Money, the pleasures money brings me, and you." -Chuck to Nate, Dare Devil (1x05)
"Did you sleep with her, huh? You son of a bitch I could kill you." -Nate
"Look, can we talk about this without your hands around my neck?" -Chuck
"What'd you do? Did you get what you wanted like you do with all those other girls?" -Nate
"Yes, Nathaniel, I took what Blair kept throwing at you and you kept throwing back." -Chuck
"Oh, so somehow you screwing Blair for sport is my fault?" -Nate
"It wasn't for sport! She needed someone and I was there." -Chuck
"Oh, so you cared about her?" -Nate
"You two were broken up-" -Chuck
"What, for how long? A week? AN HOUR?" -Nate
"Look, I am sorry, all right? I know how long you and I have been best friends, okay?" -Chuck
"No, it's not okay, Chuck. From now on, you stay away from me." -Nate
"DID YOU HEAR WHAT I SAID? YOU STAY THE HELL AWAY FROM ME, CHUCK." -Nate, A Thin Line Between Chuck and Nate (1x13)
"Come on. Let's go get drunk." -Chuck to Nate, The Treasure of Serena Madre (3x11)
"You deserve to be alone." -Nate
"I may be heartless, but you're naive." -Chuck, The Unblairable Lightness of Being (3x18)
"No one understands what we have!" -Chuck, on his relationship with Blair.
"Yeah, no one understands because it's not normal." -Nate, Shattered Bass (4x21)
"Well, look at that. Chuck Bass maturing." -Nate
"Sad but true, I'm afraid." -Chuck
"Being at St. Jude's reminded me of all the Lost Weekends we used to have. So why not graduate to a Lost Summer?" -Nate
"I'm intrigued." -Chuck
"Just spin the globe and pick a point. We can start there, then make our way back here. Like old times - bachelors who don't have to answer to anybody." -Nate
"You're a good friend." -Chuck
"One of us has to be." -Nate, The Wrong Goodbye, (4x22)
If only you could be me for a day and I could be you, we could both get what we want. But since we're not in a Jason Bateman movie, we have to think of another plan." -Chuck to Nate, The Fasting and the Furious (5x05)
."Be careful. There's a fine line between surveillance and stalking." -Nate
"Yeah, getting caught." -Chuck, Father and the Bride (5x12)
"Where's Monkey? I found his crying at my door comforting." -Chuck
"I had Ivan from housekeeping take him for a walk." -Nate
"Why? Cause you were too busy reading up on new ways to betray your best friend?" -Chuck, It's Really Complicated (6x08)
- Nate and Chuck used to sneak into Howard's liquor cabinet and get drunk, then Chuck had to go home to a full dinner.
- They were given their first joint and snuck into their first club by Carter Baizen.
- They have had many Lost Weekends together.