On the one hand, they were childhood sweethearts. It's hard to want a couple to be together after that and he briefly ruined a friendship. It was obvious Nate and Blair never would or should have stayed together from the beginning. Their relationship seemed to exist to be the source of conflict in season 1 for Blair and Serena's friendship.
After that, there was no reason for it to continue. Dan and Vanessa's relationship was one that needed to be explored at some point on-screen. Was it one that should have lasted? Probably not. Was it one that could have lasted? Again, no. It was clear from the very start that Serena and Dan would end up together. Dan and Vanessa's relationship may not have lasted, but they were two outsiders that got caught up in the drama of the Upper East Side.
However, Dan and Vanessa deserved better as a couple than they got. She was the one who got his story published in The New Yorker as unbelievable as that was. Maybe they would have had a chance if their romantic connection didn't have a scandalous beginning, thanks to Olivia.
On the one hand, leaving the city was best for Jenny. That was something that Dan and Rufus agreed on when Gossip Girl's identity was revealed in the series finale.
A GG blast made that possible. However, the events leading up to that GG blast didn't need to happen. In the pilot, Chuck tried to take things too far with Jenny on a rooftop. Dan and Serena intervened and saved her. Two years later, Jenny had her first adult experience with Chuck, something that never should have happened. Why Gossip Girl thought it was okay to have Jenny be with Chuck after what he did was a headscratcher.
It was the wrong move and one of the worst things to ever happen in the series. Yes, Serena and Nate may have first gotten together behind her best friend's back. Their hookup was the moment that started everything, really. Who knows what would have been different, if not for that? Anyone who likes anything that happened on Gossip Girl has them to thank.
It took until season 3 for the two to give a relationship a try. If Dan didn't exist, it's possible that they could have worked and ended up together. There would have been no reason for Serena and Dan to drift back together.
In the end, they sadly didn't have enough drama to last, which says something given their history. That's also why it would've been preferable to see them end up together, rather than Dan and Serena. Remember when Dan wanted to be with someone normal? Somehow, the two ended up dating briefly. There seemed to be one thing after another when it came to their relationship.
Vanessa briefly interfered with their relationship over a toast at a dinner. Olivia lied about dating a co-star and she told an embarrassing story about him to Jimmy Fallon. Olivia and Dan's relationship may have been a short, but it was packed with drama. He tried to keep her from filming a movie with a list of things college students needed to experience. They, along with Vanessa, did everything on the list, including some experimentation. It inevitably led to some jealousy. Olivia ended up leaving to film a movie and was never seen again.
So, what was the point of their relationship? In the earlier seasons, Dorota was only really seen as the Waldorf's maid but changed as the series progressed. She was also a fan favorite character and a popular guess for Gossip Girl's identity.
There were even Chasing Dorota webisodes. Her relationship with Vanya, a doorman in Lily's apartment building, was never really a main focus of the series.
However, it benefited from that because they could just be that sweet, romantic couple on the fringe of the other relationships' problems. His proposal is reason enough to love their relationship. Only on Gossip Girl could someone pretend to be someone else and then stick around. Not only did Ivy stay after everyone found out she wasn't Charlie Rhodes, but she even got some money. That wasn't the worst of it. In fact, the worst of it wasn't even the mess that was her and William's relationship.
No, that honor belongs to her and Rufus' brief romance. It was completely unnecessary since it wasn't like it was the final straw that kept Rufus and Lily apart. By that point, that relationship had run its course. Instead, it seemed like the only point of Rufus and Ivy's relationship was so Dan could walk in on them.
No one needed to see that. Serena and Carter would never have lasted, even if Dan wasn't her endgame. The show would have had her end up with Nate or probably any of her other boyfriends before Carter. However, it wouldn't have been the worst thing to have Blake Lively and Sebastian Stan's characters together longer. Carter really tried to show Serena that he changed and tried to redeem himself.
Before he can, Catherine confronts Vanessa about dating Nate and blackmails her with revealing Howard Archibald 's location if Nate leaves her.
She tells Blair, but after she mistakingly assumes that Blair isn't dealing with it, she tells Catherine's husband. However, she soon learns that was a mistake because Blair was able to convince Catherine and Marcus to leave town and pay of the Archibald debt. She tells Nate, who is more disappointed that Vanessa went to Blair instead of him. Jealous, she steals the letter before Jenny can see it. She creates a see through dress for Vanessa, and they plan to shine a bright light on her at the ball to reveal her underwear.
However, Vanessa feels guilty for stealing the letter after talking to Jenny and plans to tell Nate at the ball. Before she can, the girls spotlight her and humiliate her in front of everyone. She leaves the ball, but is followed by Nate, who reveals that even though she stole the letter he wants to be with her. They enter into a relationship. After a long fight with the van der Bilt side of his family, Nate is convinced by his cousin Tripp van der Bilt to attend the family reunion.
He brings along Vanessa and Dan Humphrey , and they meet his family. At a party thrown by his grandfather William van der Bilt the next day, Vanessa learns that Nate might abandon their summer backpacking plans to take an internship at the mayor's office. Angry that he might become a van der Bilt robot, she encourages him not to take it. Meanwhile, Blair is spiraling out of control and Nate is able to talk her back down to earth and they begin to grow closer The Grandfather.
In Remains of the J , Nate breaks up with Vanessa due to him feeling things have come to a natural end. Thinking he dumped her for Blair, she teams up with Chuck Bass to get revenge. Nate becomes disappointed with Vanessa, and asks if that's her way of becoming more like Blair.
In the finale The Goodbye Gossip Girl , Nate tells Vanessa and Dan that he plans to abandon his internship after the mayor took an interest in him.
He asks her if they can go on their backpacking trip after all, and she agrees to let him come. After their break-up, they don't have many scenes together. In Season 1 Nate and Vanessa begin a friendship which eventually turns into a somewhat relationship after they kiss.
But, Nate later breaks up with Vanessa because he feels that he doesn't have time for a girlfriend because of everything going on in his life. Also, he faces problems between Jenny Humphrey and Vanessa, Nate and Vanessa decide to go on a trip together. Nate decides to take the internship, which results in Nate and Vanessa breaking up. Vanessa reveals that Nate and her hooked up one night in Europe but that they decided to only be friends.
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