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The relationship between Dan and Serena , also known as Derena, is the friendship and romantic relationship between Dan Humphrey and Serena van der Woodsen. Dan and Serena met at a party thrown by Blair Waldorf that Dan was accidentally invited to. They had a brief conversation that led to Dan having a huge crush on Serena. In Pilot , they accidentally run into each other at the The Palace Hotel and upon returning her cell phone; Serena asks Dan on a date. They begin dating for the remainder of the first season before breaking up in Much 'I Do' About Nothing. They date briefly twice in the second season and then remain mostly off until season six. In the Gossip Girl series of books , Dan and Serena date very briefly but break up due to having nothing in common.

In the Gossip Girl series of booksDan and Serena date very briefly but break up due to having nothing in common. Soon after, Serena's old friend Georgina Sparks comes back to the city to stir up trouble.

They later resolve their issues, but Serena tells Georgina she no longer wants to be in contact with her.

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After Georgina blackmails Serena with a video of the night where they witnessed Pete Fairman, a late mutual friend, die, Serena goes off the deep end. She's rescued by Blair, Nate, and Chuck, who try to keep Dan away from the situation.

To keep Dan from knowing what she really did, Serena lies that she cheated on him and he tells her that he is done. During Lily and Bart's rehearsal dinner, Lily goes with Serena to see the Fairman's and gain closure.

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Afterwards, Serena goes to find Dan but finds out that he's with Georgina; who is planning to seduce him Woman on the Verge. He then teams up with Blair to get rid of Georgina, which they successfully do.

However, at Lily and Bart's wedding, he breaks up with Serena; not wanting to deal with the drama and struggles of their relationship anymore.

She is unsure at first, both about going and about whether she still has feelings for Dan. As a result, she asks Dan if he thinks she should go and he tells her she should; a decision she agrees with once she learns their parents are planning to rekindle their relationship.

However, she breaks up with Aaron on the plane and when she returns, admits to Dan that she misses him and they get back together.

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Soon after, Dan discovers that Lily had Rufus' lovechild many years ago and that she gave the baby up for adoption. Knowing he shares a biological sibling with Serena, he begins to distance himself from her In the Realm of the Basses.

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In You've Got Yale! Dan is instantly attracted to her and they strike up a friendship surrounding writing and literature. Meanwhile, Blair decides to take action against Rachel for giving her her first B and ends up with detention after being caught hazing her.

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Wanting even more to destroy her, Blair starts a rumor that Dan and Rachel are sleeping together. After Serena spots the two having a seemingly romantic dinner, she takes a photo and gives it to Blair; who shows it to the PTA of Constance and Headmistress Queller. When Serena finds out, she plans to charm Gabriel into giving all the money back but Dan is skeptical her plan will actually work.

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Worried about what to do, he informs Lily of the situation and Serena's plan. Lily then orders Serena to stop and when she doesn't, has her arrested for theft The Wrath of Con. In Valley GirlsDan bails Serena out of jail and escorts her to prom.

Serena and dan dating in real life

In Cross RhodesDan and Blair enter into a relationship. Serena tries to act like she's okay with it, but it becomes obvious pretty quickly that she isn't.

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As a result, Blair kicks Serena out of her penthouse. Meanwhile, she struggles with her decision about whether to be with Dan and Chuck.

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Wanting to hurt Blair after what she did, Serena seduces Dan at the Shepherd Divorce party and the two have sex.

At the same time, Blair chooses to be with Chuck and goes to tell him but is rejected. Soon after, she breaks up with Dan, much to Serena's delight. However, Dan has no interest in being with Serena and tells her that he never wants to see her again.

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