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At Lily and Bart's wedding, he breaks up with Serena, not wanting to be around the drama and problems that come with the differences in their worlds. All along, I could tell that there was something still unknown about her past and was the reason she felt the need to not allow herself any happiness.
After seeing Blair out Serena for a nonexistent drug problem, then seeing Serena take the fall to protect Online dating mthatha brother Eric van der WoodsenDan tells her that if she ever wants to get together and not talk, they can Poison Ivy.
Serena admits to Dan that she genuinely thought he could help Blair be brave. She debates whether to warn him, and does so at the dance. After the dust settles, Dan admits to Serena that he really did want to tell her but Rufus made him not. Blair, who is given detention after hazing Rachel, exacts revenge by spreading a rumor that Dan and Rachel are having an affair.
Then add in Percy's big boisterous family and two friends and Imogene didn't stand a chance of remaining aloof.
Also in the books, Dan is addicted to coffee and cigarettes but neither is shown to be of extreme interest in the show. On Christmas morning, Rufus and Alison reveal they're splitting up and that she plans to return to Hudson Roman Holiday.
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On prom night, Serena is still in jail but Dan bails her out to escort her Valley Girls. Dan eventually finds out that Vanessa applied with an original piece, so he tells Willa to undo what she did.
While at dinner, he reveals to Nate that he knows how bad he's living, but Nate orders him to stay out of it. At Asher and Jenny's party, he, along with Blair, reveal Asher is gay too. After the performance, he discovers Rachel told Yale that she was hazed by Blair, costing her her acceptance.
She was like the broken bone that healed wrong and has to be broken and reset to get it to heal properly a second time. Chuck thanks him for having his back but takes it back after learning Dan was writing about him.
Or so she thinks, until she looks closely. Get personalised ads from our trusted partners This doesn't mean more ads, it means personalised ones. Dan is clever, as he was basically the smartest in his class, and also witty and patient; he works hard for what he wants and normally achieves his goals.
Angry at Blair, she confirms a rumor about her to Nate, who ends his friendship with Chuck and break up with Blair.
Serena originally thinks Dan told Jenny and accuses him of doing so, but later figures out he didn't.
Select 'Manage options' to set your data use and sharing choices. He tries to act cool, but soon figures out that she wanted a real Humphrey date. He encourages Dan to get out of his comfort zone, so Dan begins hanging out with Chuck.
Imogene lives quietly on the estate that would have belonged to her deceased husband if he had lived, but instead went to a distant cousin two years before.
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Georgina, who becomes angry after Serena tells her never to contact her again, "accidentally" runs into Dan in the park and introduces herself as Sarah.
Chuck tells Bart that Dan is planning to expose him, then asks Dan to not to.
While at dinner, Rachel is extremely upset with the news and Dan hugs her to comfort her.