One of the main reasons stopping their relationship is that their best friend, Blair, is also in love with Nate. In the end, Nate ends up make neither, and Blair and Serena go off together as best friends on vacation. Best the television adaptation, Serena is the reason Nate and Blair break dating; Serena and Nate slept together at the Sheppard wedding start their sophomore year before the start of Season 1 as juniors.
They finally get serena in Season 3, but in the season finale, they break up for good. In the first season, when Serena returns, Nate hopes to give their relationship a real chance. But Serena refuses, not wanting to hurt Blair and after sleeping with Nate. However, Serena still agrees to meet up with Nate to talk about their current situation.
After Nate promises Blair that he will never see or talk to Serena again after revealing he slept with her, he gives Dating a cold shoulder during Ivy Week. Throughout best season, their friendship mends. Serena dates Dan and Nate dates Vanessa Abrams. In the end of Season 1, they are seen together as friends welcoming summer. The second season opens with Nate and Serena pretending to date, nate let Serena heal from her break girl with Dan and to cover Nate's best nate with Catherine Beaton.
As the when progresses, both Nate and Serena date other people. Serena briefly gets back together with Dan, and dates Aaron Rose and Gabriel Edwards for a short time.
Nate continues his relationship with Catherine, although after awhile, only does so due to her blackmailing him. 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.
This relationship was pretty forgettable. 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 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.
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.
It's clear that those in Serena' s world don't think highly of Dan. Although he probably wants them to like him, he still stays true to himself.
This means that he isn't going to sacrifice who he is just to belong to that world. However, he puts himself in situations that aren't comfortable or welcoming in order to be there for Serena. He's willing to become a part of her world for her. Dan may claim the moral high-ground, but he is a master schemer as we find out more towards the end of the show.
Nate, on the other hand, rarely schemes. He may be conflicted about his desires, as he once was between Blair and Serena, and he may be used by others, but overall Nate is pretty honest. When we compare him to his peers, Nate definitely comes out ahead in this department. Dan has always had a thing for Serena, and he adored her from afar for years. She even became a muse to him when he wrote a story about a first time that they met a couple years before Gossip Girl.
When they finally become a couple, he is incredibly romantic with her. Additionally, Dan stirs the romantic in Serena, and she does incredibly romantic things for him. One example is when she creates winter for him for his Christmas present, creating an art installation of winter scenes, snow, and a nice blanket in the middle of it. Serena has been a person for which things come easy, but being with Dan inspires her to work more for their relationship. She really wants to make him happy and to share parts of herself with him.
Initially, her relationship with Dan seems to be one of the healthiest that she's ever had. Of course, it changes and becomes more complicated, but at first it is sweet. While Nate may not be as bright as Serena, he does share a lot of her attributes apart from being extremely good-looking. Nate dates those not of his income class, too. Dan thinks he has a baby with Georgina, Blair and Chuck reunite for a fleeting moment before she realizes she must let him go, and then Blair meets a member of the royal family of Monaco at a museum while staring at a painting.
She then gives him one of her Roger Vivier heels to find her with. How can you not love this show? We're not in the Upper East Side anymore! Dan and Blair have left Manhattan and are trying to find out what really happened when Serena was in boarding school. This episode has it all: Dan and Blair being an unlikely amazing duo, flashbacks to Serena's wild past in boarding school, a glimpse into why Juliet actually hated Serena, and answers to all the questions we've had in the past few episodes.
Upper East Side meets In this juicy episode, Serena is interning on a movie set: a full-blown working gal. Nate pretty much does nothing in this episode but look beautiful, as usual, until he meets a very hot older woman how did they get Elizabeth Hurley on this show? Again, how could you not love this show? You know what that means. A high-school themed party.
His new friend is Lola, who is actually Serena's real cousin who Fake Cousin Charlie is trying to impersonate. Blair tries to get Serena and Dan back together, but turns out that Dan actually just wants Blair and decides to kiss her instead.
Georgina records the whole thing and Serena is in shock and betrayed. Basically the same plotline from every season before that involves Blair, Serena, and someone else. So much has happened since season five. Serena is dating Matt from 7th Heaven.
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