In one of the final episodes of season three, Dan and Serena sleep together and agree not to talk about it because he's with Vanessa Jessica Szohr and Serena's with Nate Chace Crawford before realizing Jenny had taken a photo of them together and sent it to Gossip Girl. At the loft, all alone once again, Dan sees the blast, then spots a take-out coffee cup with Jenny's name on the side.
If Dan were Gossip Girl, he probably wouldn't need the coffee cup to figure out that Jenny was the one who sent the tip. Also, why would Dan be so angry that the photo got out when he was the one who posted the picture to his blog in the first place? The writers must have seen this glaring plot hole because they even tried to cover it up unsuccessfully in the finale when Rufus confronts Dan after finding out he was Gossip Girl.
Rufus says, "You told the whole world about [Jenny] losing her virginity! She sent that tip in herself. She wanted to get out of New York, but she didn't feel like she had the strength to leave on her own. So she knew if Blair knew the truth, she wouldn't have a choice.
First of all, that makes no sense. Second of all, even if Jenny had requested it, why would a brother ever want to tell the world about his sister's sex life, especially when it concerns the notorious Chuck Bass Ed Westwick? Spreading rumors that the girl you want to get back together with has an STD is not something you should be particularly proud of.
One could argue that Dan may have wanted to ensure no other guy tried to sleep with Serena a truly sociopathic motive in and of itself , but things get confusing when Dan goes on to post a photo blast of him at the Student Health Clinic which simultaneously blows up his relationship with Vanessa and tells all of Manhattan he has an STD.
Dan may have just wanted Serena to get the help he thought she needed, but telling everyone she is an addict is cruel, especially when it was all a set-up to begin with. Arguably one of the biggest plot holes with Dan being Gossip Girl are the times he outed himself as a cheater.
This was either next level manipulation or Dan has multiple personalities. First in season two, Dan has an affair with his teacher and gets her fired. Then he posts a picture of himself in bed with Serena when he was dating Olivia Hillary Duff in season three, and by the fourth season, he posts a picture of himself fake-kissing Blair Leighton Meester. Dan, what are you doing?
First of all, being known as a cheater is never a good thing for your reputation. Why would Dan write that unless he knew who the "ghost" was or had at least seen her? But then he totally falls for Georgina's fake identity! The only explanation: Dan knew Sarah was actually Georgina the whole time and went along with it for the drama??
Not only was Dan outing someone which is Maybe Dan HAD to post every tip he received to protect his identity. Although was it really worth it?? He thought it was ruining Jenny's privacy and really inappropriate, but He basically ruined Jenny's social prospects, not to mention he wouldn't give the Asher thing a rest. Asher was a dick, but he didn't deserve to be outed by Gossip Girl. This basically caused his breakup with Serena, because she found out he already knew and didn't tell her.
Plus it was bad for Rufus, who had asked Dan not to say anything until Lily could tell Serena herself. Just all around a bad call, and it also didn't even seem to come from any tip but from Dan himself. He didn't need to post the tip — Blair gave no proof, and in the past, Gossip Girl had required photos or something.
Plus, all Blair wrote was "Lonely Boy and Ms. Mary Kay Letourneau alert! Dan went out of his way to make up a bunch of lies about him and Ms. Carr and fueled further rumors. The only explanation: Maybe Dan somehow knew this rumor would get Blair in trouble, which means he wanted to take down Blair and also didn't care who he hurt along the way.
Maybe he thought the rumors would somehow help his chances with Ms. Carr or make him seem cool? Since Jenny sent in the tip and apparently knew he was Gossip Girl at that point, couldn't he have just The only explanation: Dan was trying to break up with Vanessa without actually having to do it, and he also wanted to ruin Nate and Serena's relationship so he could slide in and date Serena. Dan acted really mad when he saw Jenny's cup and realized she sent the blast. But wouldn't he have already known she sent it as he'd received the tip from her?
I mean, it would have been great to never reveal it. But of course, the reasoning behind why Nate was Safran's first choice makes slightly more sense than the choice to give the title to Lonely Boy. It was Nate until the day I left," Safran admitted. With Dan, it makes sense because he wanted to find a way in,". And while fans may not agree with the thought of Nate played by Chace Crawford being behind the Manhattan madness, Safran has previously mentioned that that Eric van der Woodsen, Serena's little brother, was once considered for the role.
Nate never sent in a tip in through all of those episodes, which is when we're like, 'Oh, well then he's Gossip Girl. Safran is returning for the GG reboot, and while we don't know when the show will premiere, we do know that it's set about years after the finale, so in "real time," and will feature high schoolers at Constance Billard Academy, Serena and Blair's alma mater. The original cast won't be in the new show we think , save for Kristen Bell as narrator , and the cast will be more diverse than the '00s version.
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