Gossip Girl: 10 Reasons Why Serena and Dan Aren’t Real Friends

Gossip Girl’s Serena van der Woodsen and Dan Humphrey have a complicated history full of lies and power moves. Were they really friends at all?

Throughout the entirety of Gossip Girl’s run, each of the main characters had managed to either date each other or hate each other. Part of the show’s fun is guessing who’ll end up with who, and Serena and Dan did not disappoint. From being friends to dating and then having a shared sibling, the two never seemed to have a moment of peace.

Whether they were meant for each other or not, their relationship is a hot topic among fans, even though they were friends for a good 3 seasons. Looking past their break-ups and make-ups, here are 10 reasons why Serena and Dan aren’t real friends.

9 They Dated And Broke Up Several Times

Dan and Serena were an on and off couple for the majority of the first two seasons. Their budding romance was sweet at first, but Serena’s secrets were too much to handle, so Dan broke up with her. However in season 2, when Dan decided he wanted her back until they realized that dating would be a bad idea.

Their on and off romance continues to the point where they break up so much that it’s questionable whether they liked each other in the first place. After all the drama, eventually, they end up getting married in the series finale.

8 They Don’t Trust Each Other

Despite the fact they willingly want to date each other (and end up getting married), Dan and Serena don’t trust each other. At the end of season one, Serena gets into a complicated mess with her frenemy Georgina Sparks about the death of an old friend. Serena is so scared of Dan finding out her secret that she lies to him and says that she cheated on him.

Dan eventually finds out the truth and decides that her secretive world is too much for him to handle, they break up. They never seem to trust what the other is doing.

Throughout Gossip Girl, Dan Humphrey goes on about how little he wants to do with New York’s Upper East Side and its residents. Although without, he wouldn’t have met Serena or any of his other friends, he talks a lot about how much he dislikes the way of living.

It’s safe to say that Dan criticizes Serena for how she lives when he benefits from it more than he would care to admit. In fact, Serena and the Upper East Side benefits him in more ways than one. The only real reason that Dan is so focused on New York’s elite is that it’s the focus of his book and he is Gossip Girl.

7 Dan Uses Serena

If Dan appreciates his friendship with Serena, then he’s got a pretty interesting way of showing it. If you look closely, their friendship revolves around a class struggle. Serena is desperate to have something normal, and Dan is just that. However, it’s safe to say he uses her for attention. When he publishes his book, her reflected character is obvious.

Being associated with her gets him more opportunities, and he becomes engrossed in the world of Gossip Girl. She is always a topic of his writing, whether it be for novels, articles or Gossip Girl, and it gets him the right amount of attention every time.

6 Dan writes a Book About All His Friends

One of the most shocking moments of Gossip Girl is when Dan’s book gets published and it ends up being based on the lives of all his friends. Of course, this wouldn’t have been a problem if it hadn’t been for the fact that he told no one and that the Upper East Siders all had to find out themselves. Dan lost a lot of friendship points, especially with Serena.

She was reflected particularly badly in his book, and even though he explained that parts of her character weren’t accurate, she wasn’t very impressed.

5 Dan Posts a Scathing Article About Serena

Just as things are finally starting to look good for Dan and Serena, Dan messes things up completely. When Serena and Dan decide to host Thanksgiving dinner for their friends, things start to go south very quickly when Dan posts a scathing article about Serena (and yes, they’re dating at this point).

Serena is furious and rightly so, she once again breaks up with him. Either Dan has a broken moral compass, or he doesn’t know what feelings are, because he has written awful things about Serena too many times to count.

4 Serena Lies To Dan To Secure The Rights For His Book

Right after Dan’s book is revealed to the world, Serena is forced to mend their friendship because her boss wants the movie rights to his book. Because Serena hasn’t learned anything about lying, she lies to Dan and tells her that she forgives him, even though she hasn’t and she’s still very hurt by what he did.

After this, she uses her friendship with him and questionable legal methods to get the rights. While she ends up getting fired for protecting his book, the main message here is that if they were truly friends, she wouldn’t have lied to him, to begin with.

3 Serena Lies About Their Fake Relationship

Another fan-favorite pairing is the unexpected relationship between Dan and Serena’s best friend, Blair Waldorf. When Blair’s love interest Louis accuses her of having an affair with Dan, Blair asks him and Serena to pretend to date. It’s safe to say that Serena gets a little too into being a pretend couple and starts to have feelings for him again.

When Blair tells Serena she doesn’t need to pretend anymore, she ignores it and decides against telling Dan. Of course, Serena wants what she can’t have and when she tells him she loves him, Dan rejects her because he’s in love with Blair.

2 Serena Gets Jealous About Dan’s Friendship With Vanessa

Fans of Gossip Girl know by now that jealously is a running theme throughout the show. Whether it’s Dan being jealous of Serena and Nate, or Serena being jealous of Dan and Blair. The first time we truly see Serena van der Woodsen get jealous is when Dan’s best friend Vanessa enters the picture, or when absolutely any other girl enters the picture.

To make matters worse, Dan and Vanessa used to have feelings for each other, and Serena sees her as competition. Both girls have an on and off feud throughout the show and are jealous of each other.

1 Dan Ends Up Being Gossip Girl

The biggest and most obvious reason why Dan and Serena aren’t real friends is that Dan ends up being behind Gossip Girl. While Serena and the rest of the gang react surprisingly well to the news, fans expected them to be furious, especially Serena. All along, Dan had been documenting everybody’s moves and mistakes.

He willingly humiliated and bullied Serena through Gossip Girl, and almost ruined her life. To anyone watching, this was a huge betrayal, and Dan should have been left alone as Lonely Boy, with no friends because once again, he has no moral compass. But neither does Serena.

About The Author

Evi Lodge
(69 Articles Published)

Evi Lodge is a student and avid cinema-goer. She currently writes list articles, and when she is not writing or studying, she’s probably reading a good book and catching up on pop culture.

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