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Does Dan date a teacher?

Serena discovers that Dan, her boyfriend is cheating on her with the same teacher Blair is trying to take down, Rachel.
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What happened with Dan and the teacher?

During his senior year, Dan has an affair with his Shakespeare teacher, Rachel Carr. She's not that much older than him and he is 18 at the time, so what happens is technically not illegal.
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Who does Dan end up dating?

A five-year flash forward takes place and shows the wedding of Dan Humphrey (Penn Badgley) to Serena van der Woodsen (Blake Lively). "New York, I Love You XOXO" received favorable reviews from television critics.
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Who does Dan date in Gossip Girl?

Serena was overjoyed at the revelation, stating that Dan, through Gossip Girl, had written her and everyone else a seven-year love letter and made her realize that she belongs in the Upper East Side with Dan. Five years later, Dan and Serena get married, surrounded by their closest friends and family.
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Who does Dan date in the books?

Dan dates his male coworker Greg in the books.

Dan's sexual orientation isn't explicitly confirmed in the books, but he does date both men and women.
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Gossip Girl is Revealed

Who did Serena lose her virginity to in Gossip Girl?

In the show, Serena slept with Nate at the Shepherd wedding during summer break, seemingly both losing their virginity to each other.
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Who does Blair lose her virginity to in the books?

Incidentally, the show winked at this fact by making Chuck's 'character' queer in Dan's book Inside. In the books, Nate is Blair's main love interest and both Serena and Blair lose their virginities to Nate.
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Who does Dan cheat on Blair with?

Her connection to Chuck never really allows her to feel too deeply for anyone else, even the guy she married. Dan cheats on Blair with Serena around the same time Blair decides she'd like to leave Dan for Chuck. Dan doesn't give up right away, instead trying to guilt and worm his way back into Blair's life.
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Who did Dan really love?

Dan's unconditional love for Blair was the biggest standout in their relationship. There was quite literally nothing Blair could do that would make Dan give up on her. Blair confided in Dan more than anyone else, and he knew all of her deepest, darkest secrets.
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Did Serena and Dan date in real life?

During the series' six-season run, however, there were several on set romances. While portraying on-again, off-again couple Serena and Dan, Lively and Badgley dated IRL from 2007 to 2010.
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Why did Gossip Girl end so abruptly?

The truth is, Gossip Girl, for all the love fans had for it, just wasn't doing well in its final years. After Season 2, the ratings for the series were on a steady decline. Season 5 garnered an average of 1.7 million viewers, which was a sharp contrast from the 2.35 million that came to watch Season 1.
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Who does Dan marry in Gossip Girl?

Dan has an on-again-off-again relationship with Serena van der Woodsen and the two have the longest running relationship on the show. Dan and Serena finally get married in the finale.
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Did Dan love Blair more than Serena?

though with blair, he was always there for her, through every hard choice and mistake, he knew her flaws, and accepted all of them. he understood her, related to her, and enjoyed being with her more than he ever did with serena.
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Why did Cece leave everything to Ivy?

Cece chose to overlook her blood relations when planning out her will and left everything to the girl who cared for her in her final days - Ivy Dickens.
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Did Serena and Chuck ever sleep together?

Novel Series. In the books, Serena and Chuck hook up for 3 weeks until gossip girl finds out and creates an eblast and Nate finds out.
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Does Rufus and Lily end up together?

Lily (finally) marries Rufus in an elegant outdoor wedding during season three, in which Serena plays bridesmaid yet again. While we have to wait until the series finale for this moment, Blair and Chuck eventually tie the knot in an intimate ceremony that is the antithesis to Blair's first wedding.
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Did Blair actually like Dan?

Putting aside her insecurities she admits to both Serena and Dan that she too has feelings for Dan. Serena then gives Blair her blessing, stating that she does not want to be an obstacle in Dan and Blair's relationship.
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Does Dan ever become a good guy?

Dan Scott is the main antagonist and a selfish man in seasons 1 to 3 (and some of 4) he became an anti-hero in seasons 5 to 8 and is finally redeemed in season 9 when he takes a bullet to save Nathan's life. He dies later in hospital.
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Did Georgina actually like Dan?

It is then revealed that she has grown very attached to Dan. Because he broke things off with her, she plans to find another way to cause more damage.
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Did Serena really cheat on Dan?

A hypocrite with a capital H, Dan made a huge deal about how Serena had slept with her teacher, Ben, when she was at boarding school. It turns out Serena didn't sleep with her teacher but only had a crush on him; Lily added in the sleeping together rumor to "save" Serena's reputation.
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Is Blair pregnant with Dan's baby?

The show also explores romances between Blair and multiple male leads, resulting in occasional love triangles. In the fifth season, Blair is revealed to be pregnant with Prince of Monaco, Louis Grimaldi's child. However the child later dies before birth after a car crash Blair and Chuck were in.
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Did Louis ever love Blair?

In the beginning of the season, Louis proved to viewers he was really in love with Blair: he sided with her over his family (even possibly giving up his title) and was thrilled when he heard he was going to be a father.
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Is Blair's baby really chucks?

And, in a scene that fans have been waiting for since the start of the new season, Blair shows up at Chuck's apartment immediately following her finding out the truth. She tells Chuck that she's pregnant and that Louis is the father. She explains that she didn't want him to hear it from someone else.
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Did Blair really sleep with Jack?

However, Chuck gets there before anything happens and physically restrains him. After that, he's sent back to Sydney. In the finale The Goodbye Gossip Girl, Chuck finds out Blair slept with Jack from the exposing Gossip Girl blast.
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Did Jenny know Dan was Gossip Girl?

In the finale, Dan makes a comment that Jenny had known he was Gossip Girl for years, and that he would only write about her when she asked him to.
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