Why do dan and vanessa break up

Nate and Blair broke up after Nate cheated on her with Serena. However, the two got back together in season 2 for a while. Fans were not impressed by their relationship and were not shocked when they broke up again. While the breakup was understandable, the reasoning behind it all seemed forced. Blair thought the relationship with Nate was like being with a high school boyfriend, and the two quickly broke up and remained good friends.

Some thought this was only paving the way for Blair and Chuck , but still wanted a bit more from the two before breaking up. Dan and Vanessa were childhood friends, and a lot of people thought they would be good together.

While Vanessa broke up with him because he was with Serena , the reason was valid, but fans still wanted to cling onto hope with these two. They shared a lot of similarities, and their energy bounced well with each other.

After knowing one another for years, viewers thought they could work it out, but Vanessa left him in the dust. Many knew Carter Sebastian Stan and Serena probably wouldn't last, but Carter did change himself for the better during the relationship. Fans thought that Serena was the most honest and authentic when she was with Carter.

But when Carter tried to fix things himself, Serena stepped in and fixed things for him, which made Carter upset. He told Serena that he would rather have her hate him than feel sorry for him, and he leaves. Fans wished Carter could have stayed around a little while longer. Nate and Serena were a surprisingly good couple. While they came from different backgrounds, they learned from one another and got along well. Nate ended up breaking it off because he felt the relationship had met its end.

Viewers were confused when they broke up, especially when later they went on a trip together and hooked up. Even when Nair Blate? Their friendship remained cute and consistent long after their romance ended, though, which earns them a respectable seventh spot.

Okay, admittedly our view of Carter Baizen might be skewed by Sebastian Stan's role in the Captain America movies, because it's hard not to ship anybody with Bucky Barnes. Serena and Carter were never going to be a long-term thing, what with him being kind of a shady drifter and her having at least vague aspirations to do something with her life, but they were hella fun together and Stan had more chemistry with Blake Lively than almost any of Serena's other beaus.

Had the finale ended with Carter rocking up to whisk Serena away from her ill-advised wedding, The Graduate style, we would have been more than okay with that. From the moment Vanessa showed up in Brooklyn wearing her unresolved feelings for long-time BFF Dan on her sleeve, it was clear they were going to hook up eventually. What was surprising was just how well they worked together as a couple, once that threesome with Hilary Duff forced them both to acknowledge the obvious.

Basically every single good thing that ever happened in Dan's career was because of Vanessa, and she was the only person who could relate to him creatively — even though she was by all accounts a way better writer. Dan was so terrible by the show's end that it was hard to ship him with anyone other than loneliness, but had Vanessa still been around she might have smacked some sense into him.

Or at least inspired him to do something better with his time than be Gossip Girl. We could have had it all, guys. Remember the very first time Dan and Blair shared a scene, in season one's 'Bad News Blair' above , and it was unexpected and lovely and a totally authentic moment of connection between two characters you'd never expect to connect?

But then… Something weird happened. We'll never know exactly what went down in the writers room midway through season five, but Dan transformed from a sweet guy into a sociopath, sabotaging Blair's wedding and isolating her from everyone who wasn't him. Eventually the whole relationship was later retconned into an afterthought, with Dan claiming he'd only ever wanted Blair because he was afraid of his love for Serena.

Or something. We'd given up caring by this point, and seemingly so had the writers. RIP, Dair. Technically Eleanor and Cyrus should be number one, because they're the only genuinely flaw-free couple in the Gossip Girl universe, but their screen time is a little too limited to bag the top spot. Eleanor was a pretty strong contender for world's worst mother in the first season, but under Cyrus's adorable influence she became warmer and more supportive towards Blair, while Cyrus himself was basically the perfect stepfather.

These two are proof that real love is possible on the Upper East Side. In The Lady Vanished , both bring dates to a dorm beach party throw by Vanessa's hall at NYU but hook up, realizing they have real feelings for the other. As a result, they begin a friends with benefits relationship but finally begin dating in The Sixteen Year Old Virgin.

Soon after, Dan reveals he is applying to the playwriting program at Tisch. Not knowing that they are only accepting one NYU transfer, Vanessa applies as well and is accepted. However, Dan tells Willa Weinstein that she applied with a play she wrote based on one of his stories and Willa tells her father, who is on the admissions board.

Even though Dan is eventually able to fix his mistake, Vanessa is hurt that he wasn't honest with her about how he felt about her getting in instead of him Dr. When he tells her that he knows, she insists on staying in New York to save their relationship but he pushes her to accept the offer.

She does so and the two plan to have a long distance relationship while she is gone. As a result, she and Dan break up. When Vanessa returns from Haiti, she finds that Dan has shut everyone out of his life.

She is disgusted to discover that Dan is the father to the worst character in gg history's newborn baby, Milo Humphrey , but tries to support him anyway Belles de Jour.

Meanwhile, Nate and his new friend, Juliet Sharp , try to get Dan out of the picture for Serena's affection by reuniting him with Vanessa. Their plan works and the two get back together Double Identity. Right before she does so, Georgina returns and says she is leaving with Milo. Despite this, Vanessa moves in with Dan anyway The Undergraduates.

Meanwhile, Dan has begun getting closer with Serena, a fact that makes Vanessa increasingly uncomfortable. She tries to tell Dan that she didn't do it, but leaves to go stay with her parents for awhile anyway. Their plan works, but gets out of control when Juliet drugs Serena into an overdose. On Thanksgiving, Vanessa returns to town and finds out what happened. After Juliet convinces her that she will lose Dan and all the Humphreys if they find out she was responsible, Vanessa singles out Jenny as the culprit.

However, Jenny tells everything to Blair and informs Vanessa that she won't be able to lie her way out of that one. Vanessa then leaves again to go to her parents Gaslit. In The Kids Stay in the Picture , Vanessa overhears that Dan and Blair kissed and tells Serena, who doesn't believe her at first, but eventually learns she was telling the truth. In The Princesses and the Frog , Serena's cousin Charlie Rhodes sets Vanessa up to make it look like she wanted to ruin her blooming relationship with Dan.

Dan falls for the stunt and thinks Vanessa is really out to hurt him. However, both are surprised when Rufus informs them that Charlie has stopped taking her medication and is at risk for a breakdown. The two search for her, along with Dan. Vanessa goes to the loft in case she shows up there and finds a story that Dan has begun working on. She is shocked by how good at is and encourages him to publish it. He refuses, saying it's a satire of his life and friends and doesn't want it to get out ever.

She asks them to forward her the royalty check, which she will pass on to Dan.