"I remember the first time I ever saw him. Maybe we were just little kids but I knew... he's the one I want to marry."
-Blair on Nate, Victor Victrola
Blair and Nate grew up together on the Upper East Side, along with their respective best friends Serena van der Woodsen and Chuck Bass. According to Chuck, the two have been dating since kindergarten and their parents always planned on the two of them marrying. Before Pilot, Nate loses his virginity to Serena. When Blair finds out, she's shocked at first but eventually forgives him. However, they officially break up in Victor Victrola due to Nate not loving Blair. They get back together in season two's Remains of the J but break up for the last time in Valley Girls; due to feeling like their relationship has run its course.
Like the television adaptation, Blair and Nate grew up together in Manhattan. Jealous of his infatuation with Serena, Blair always tries her hardest to make sure Nate doesn't stray from their relationship. Nate finds her to be clingy and is periodically annoyed with not having sex with her. They date on and off for the first few books, but break up officially in Nobody Does It Better when Blair sees him having sex with Serena.
In the book Only in Your Dreams, Nate shows that he still has feelings for Blair. She forgives him for sleeping with Serena, due to her being happy with her new boyfriend, Lord Marcus. This causes Nate to become jealous of their relationship because of his lingering feelings for Blair. Eventually, Nate professes to Blair that he loves her more than he ever loved Serena. However, he ends up with neither Serena or Blair as he leaves to travel on a boat to avoid becoming in between the two.
In Pilot, Nate and Blair are in a relationship. Blair hears that Serena is back in the city and tries to have sex with Nate for the first time before he finds out. However, he discovers that she is before they can do it. A few days later, Blair again tries to have sex with Nate but when he comes over, he admits to her that he already lost his virginity to Serena before she skipped town. Shocked, Blair kicks Nate out of her penthouse. Soon after, she decides to forgive him and ice Serena out instead. At the Kiss on the Lips party, she orders him not to talk to Serena and he agrees; but is annoyed that she is telling him what to do.
In The Wild Brunch, Nate asks Serena to meet him in Chuck's suite at The Palace Hotel so they can talk about things during Bart Bass' annual foundation brunch. She agrees and they make plans to excuse themselves. However, Chuck decides to help Blair consummate her relationship with Nate by giving her a key to his suite to seal the deal. Blair brings Nate to the suite but is surprised to find Serena there waiting for him. Jealous that they were planning to meet up, she goes down to tell Serena's new boyfriend Dan that she slept with Nate. Later, Nate tells Blair that she either needs to forgive him for what he did or end things. She chooses to forgive him and stay together. At the masquerade ball in The Handmaiden's Tale, Blair enlists Serena's help to pull off a scavenger hunt for Nate, where his prize is having sex with her. Serena agrees to help but at the ball, the last thing on Nate's mind is the game. At the end of the night, he mistakes Jenny Humphrey for Serena and admits to her that he still has feelings for Serena before kissing her.
In Victor Victrola, Blair hears from her mother, Eleanor Waldorf, that Nate is planning to give her his great grandmother's diamond ring. Soon after, she learns from Jenny about what happened at the masquerade ball. During a dinner with her mother, Nate, and Anne and Howard Archibald, she tries on the ring against her wishes. Later that night, Blair witnesses Howard punching Nate in the face and being arrested. She confronts Nate about his feelings for Serena right after, then asks if he loves her. When he doesn't answer, she breaks up with him. That night, she loses her virginity to Chuck. On Blair's seventeenth birthday in Seventeen Candles, she hopes that Nate will reverse his decision to distance himself from her and doesn't tell anyone they're broken up. Meanwhile, Nate is dealing with the recent scandal involving the arrest of his father for fraud and embezzlement. Not wanting her family to suffer anymore, Anne asks him to get back with Blair to secure Eleanor's support through the scandal. At Blair's birthday, Chuck admits he has feelings for her and makes a bet that Nate won't call at midnight the way he does every year. Blair, confident Nate will call, takes the bet. However, midnight comes and goes without Nate's call. Upset by this, she confesses to all her guests that they're broken up and ends up hooking up with Chuck again that night. Nate tells his parents that he won't pretend to be interested in Blair to get to her mother.
In Hi, Society, the Archibald family scandal has subsided. Finally not feeling stressed anymore, Nate realizes he misses Blair; especially when he learns she will be attending the Debutante Ball with someone else. He goes to her apartment and tells her that he misses her, then pleads with her to go with him instead. She accepts, and a jealous Chuck schemes to keep them apart. He sets up Nate to punch Carter Baizen at the ball, resulting in getting him kicked out. Later that night, Blair realizes what Chuck did and has sex with Nate.
Chuck and Nate head to Monaco for Christmas, but return shortly after. Knowing he has information to ruin her relationship with Nate, Chuck orders Blair to stay away from him. She tries, but Nate is working hard to get her back. After a school pool party goes wrong, Nate willingly takes the fall for everyone to protect Blair from hurting her chances at Yale, her dream school. However, the two eventually get back together (School Lies). Soon after, in A Thin Line Between Chuck and Nate, Blair has a pregnancy scare and turns to Serena for help. Knowing Blair has slept with Chuck, Serena goes to see him to ask if he can convince Blair to take a test. Chuck reveals to her that if it's anyone's baby, it's Nate's. Serena goes to see Blair, angry that she never said anything about having sex with Nate. After Blair blows Chuck off, he sends a tip to Gossip Girl that Blair slept with them both. When Nate finds out, he's convinced it's a lie until Jenny, having overheard Serena tell Dan, confirms the information. As a result, he breaks up with Blair.
In The Grandfather, Blair is still hurting over rejection from Chuck and Yale, along with every other problem in her life. At a party thrown by Nate's grandfather, William van der Bilt, Blair is rude to everyone before locking herself in a room alone. Nate eventually stumbles upon her, and gives her a pep talk into becoming more confident and fixing her life. Surprised at how much he's matured, Blair listens earnestly. That night, he walks her home and she asks him to stay with her. That same night, Chuck comes by to see Blair but finds Nate's blazer and realizes he's with her. After this, Nate and Blair begin hanging out again. However, Chuck tries to talk Blair out of being interested in Nate; reasoning that they never had passion and Nate is still dating Vanessa. Realizing she's becoming interested in him again, Blair tries to talk him into breaking up with Vanessa. He does, telling her that things have come to a natural end. Mad that he lied to her, Vanessa teams up with Chuck to ruin Nate and Blair's relationship. However, their efforts fail as Nate and Blair get back together (Remains of the J).
In Seder Anything, Blair is invited to attend Nate's cousin Tripp van der Bilt's wedding to Maureen van der Bilt. While attending the rehearsal, she reveals to William that she was rejected by Yale and her life is a failure. He agrees to help her fix things if she convinces Nate to attend Yale. She accepts his deal, but realizes she made a huge mistake when Nate outs William for having his father investigated by the FBI. Angry that she failed to hold up her end of their deal, William tells Nate about the deal she made with him. While he's angry at first, he forgives her when she apologizes.
In Southern Gentlemen Prefer Blondes, Nate notices Blair is stressed about their being at opposite ends of the city for college. Trying to curb her worries and keep her away from Chuck, he buys an apartment for them to live in together. That night, he tells her about the apartment and she agrees to move in with him. However, instead of spending the night with him there, she chooses to go with Chuck to pursue Georgina Sparks to find the truth about Serena's new boyfriend, Gabriel Edwards. The morning after, she realizes Chuck never needed her to come and only asked her to keep her away from Nate.
After scheming against Gabriel and Poppy Lifton, Serena ends up getting arrested. After the arrest, Blair tells Nate that she doesn't think they should move in together. He agrees, and they decide to go to prom together (The Wrath of Con). In Valley Girls, Nate and Blair attend prom together. They win Prom King and Queen, and dance together. While they dance, they break up; both knowing that their relationship is truly over and a thing of the past. Later that night, Blair admits to Serena that she knows Nate was just her high school boyfriend.
When Nate returns to Manhattan with his new girlfriend, Bree Buckley, Blair is suspicious of her. Her suspicions later prove to be correct when it turns out Bree was just using Nate to get to Carter Baizen (Rufus Getting Married).
After realizing her performance review might be less than desired, Blair enlists Nate to sleep with her boss, Epperly, to help relax her. He doesn't succeed, but is willing to help her anyway (Panic Roommate).
Blair: I saw your father get arrested! Why didn't you come to me? I would have listened.
Nate: I've tried, Blair. But every time I try, something's got your attention. A dinner party, you know, a masked ball.
Blair: Yeah, let's talk about that masked ball. Let's talk about how I was waiting for you to find me so that we could finally be together, you were confessing your feelings and kissing Serena. I thought I was doing everything right.
Nate: It's not your fault.
Blair: Do you love me? (is met by silence) You should deal with your father. He needs you. You know what? I don't.
-Victor Victrola (1x07
Nate: You know, all this time I felt bad for everything I've done. And when you said you wanted to leave the past in the past I didn't know you were talking about your past.
Blair: You had just broken my heart, I made a decision I was in no condition to make.
Nate: But you're clear headed now, right?
Nate: Then you'll understand perfectly when I say I want nothing else to do with you, Blair. You and Chuck deserve each other.
Nate (on seeing Blair in her lingerie): Whoa, hey Blair.
Blair: It's Anna Karenina. You never read it. Don't worry about it.
Nate: I never do.
-The Hurt Locket (3x13)
Nate (on Chuck): Whatever he did, I'm sure you could find a suitable punishment for him.
Blair: There is no punishment for what he did.
Nate: You're Blair Waldorf. Punishment is your middle name.
Nate (on William and Holland's plan): No wonder you admire it. It's almost like something you would do.
Blair: Thank you. It does have the fingerprints of my genius.
-Ex-Husbands and Wives (3x21)
Blair (on Nate sleeping with Epperly): You better not be selfish, Archibald. You know what I mean. A woman remembers.
Nate: This is why you've been dragging me around?!
Blair: What's the big deal? It's not like you haven't done it before! Just think of her as a younger more flexible Lady Catherine.
Blair: Let's go. You are going to help me get 650 gift bags from 29th Street in 20 minutes or so help me Archibald, I will tell everyone what your favorite movie is.
Nate: Hey! Don't knock the Sound of Music. It's got nuns and Nazis. Julie Andrews was hot.
-Panic Roommate (4x14)
- At the strike of midnight on Blair's birthday, Nate calls her to say happy birthday.
- They talked about going to the Debutante Ball together since they were ten years old.
- Blair always made Nate watch her favorite movies (Breakfast at Tiffany's and Roman Holiday) with her.
- Nate hasn't eaten pork since he saw Babe with Blair.
- Blair is the only one who knows Nate's favorite movie: The Sound of Music.