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For those of you who consider to be true Gossip Girl fanatics, you have been anticipating the premiere of this new season since the cast left us with one too many cliffhangers at the end of the fourth season. Serena was beginning the process of assisting a mysterious new man turn the classic, The Beautiful and Damned, into a film. Dan made the decision to go to the Hamptons without his family. Blair received what seemed to be an unwanted approval from Chuck to marry her Prince of Monaco while also possibly continuing her surprising friendship with “lonely boy” Dan Humphrey. Meanwhile, Chuck, thinking that Blair is happily engaged and finally where she belongs, takes off on a crazy adventure with recently single Nate Archibald (remember he split from enemy of Bass Industries, Russel Thorpe’s daughter in the season finale). And what happened to Charlie - Serena’s supposed cousin who had a breakdown in the season finale that brought her home, or rather back to Lily Humphrey’s sister who hired her to play her daughter? Will she be back in season 5? Finally we come to the last cliffhanger of the season: the positive pregnancy test shown in the abandoned garbage can. Who’s pregnant? What’s next for this gorgeous upper-east side gang? The time has finally come. Season 5 begins now!
We are brought back into the lives of the infamous Upper East Siders with Serena on the set of the movie she is assisting with. The glamorous, and usually waited on Serena Van Der Woodson, is now the one doing the waiting while delivering coffees to her supervisors. This is when she receives her best friend Blair’s “save the date” card.
Next, the audience finds Lonely Boy participating in a softball game, a shock to anyone who knows the true Dan Humphrey doesn’t play sports, in the Hamptons. He learns of a mysterious book that will be published in Vanity Fair. The editor who informed Humphrey of this news says the writing reminds him of Humphrey’s writing that he’s read in the past. Humphrey quickly realizes that it is in fact his story. Dan never wanted this story to get out and he will do anything to stop it.
The scene quickly changes and viewers find Chuck and Nate living it large on a yacht in a harbor somewhere in L.A. when Nate also receives Blair’s cards but chooses to hide them from Chuck. “Golden boy” must be enjoying Chuck’s new “yes to everything” attitude and is not willing to risk ruining it with news of Blair and her fairytale. After the audience catches a glimpse of all of the show’s characters, viewers finally find the happy couple, Blair and Louis, back in New York planning their wedding. But are they truly happy? It seems that the battle between Blair and Louis's mother, the Princess of Monaco, is heating up more than ever when she tries to control their entire wedding. During the wedding planning battle, Deroda reads a Gossip Girl blast that Blair receives on her phone reminding all those who are watching of the new pregnancy that was mysteriously unveiled during the season 4 finale. Both Serena and Blair aren’t drinking. So whose baby is it?
Deroda conspicuously questions Blair about the possible pregnancy. If it is in fact Blair who is pregnant, this could turn into a real “royal” issue. Serena brings Chuck and Nate to the set that she has been working on. After experiencing this new life, Nate comes to the conclusion that something needs to change in his own life. After all the controversies he’s been involved in over the years, (his father, Juliette, etc.) he is ready to make a new “Nate Archibald.” “Sometimes I just wish I could reinvent myself,” he admits to Serena.
And this is exactly what Serena promises to Nate when she brings him to a work party. As Serena gains more responsibility from the director of the movie, her supervisor becomes angered by the idea that Serena could be taking over his position. When the hardworking socialite completes all of the tasks she is give with flying colors, her envious supervisor takes matters into his own hands and makes her look terrible in front of her boss by sending her on a mission to obtain medical marijuana for an actor suffering from drug issues. Meanwhile, Dan tries to get a hold of Vanessa. He is furious with her for publishing his story without his consent, especially because he knows the only reason the magazine is interested in the story is because it speaks of the future Princess of Monaco, Blair Waldorf. Dan knows the only way to truly stop this story from being printed is to enlist the help of none other than Prince Louis.
Unfortunately for Louis, Dan reaches out at the wrong time. The prince is attempting to show Blair that he is not afraid of standing up to his mother by taking her to the Gala that anyone besides those of royalty is not aloud to attend. When Blair comes under the impression that Louis stood her up, she runs straight into the arms of none other than Dan Humphrey. When Blair tells Dan why she is so upset, instead of telling the future bride what her prince charming is up to, he agrees to Blair’s plan to escape the city and hideaway in the Hamptons. Just as the pair was about to leave, the prince shows up. Poor Humphrey just can’t catch a break it seems. Dan is forced to explain to Blair how Louis was in fact protecting her and Blair questions why he would almost allow her to let go of her future life. Gossip Girl says it best with: “Three words and eight letters don’t come out right when no one wants to hear them.”
Let’s not forget about “Lonely boy’s” bud, “Golden boy” Nate Archibald, at the party with Serena. He meets a mysteriously older woman, sounds like something Archibald would do, and quickly becomes involved with her. The audience learns later that this meeting was just an accident. A secretive phone call the woman makes alludes to the idea that there was a reason they met.
When the audience left Serena, she was under the impression that after the marijuana incident she would be fired from the movie. To her surprise, the director actually offered her a job to continue working for her. She admired Serena’s hard work and dedication and Serena happily accepted. Now that Serena is staying in L.A., she manages to run into cousin Charlie, otherwise known as Ivy, working at a restaurant. Ivy quickly runs off with Serena, pretending to be Charlie once again. One can only imagine what would happen if the van der Woodson’s found out the truth about “Charlie.”
Chuck seems to be the true shocker of this episode. As he continues with his “yes to everything” attitude, he begins to question what he really is doing with his life. He tells Nate and Serena that they all need to grow up and start taking responsibility for themselves. A sassy response from Serena that Chuck should write a book leads to Chuck returning to his old confident self. “People like me don’t write books, they’re written about.”
The pregnancy scare seems to be resolved when Deroda comes to the rescue by admitting to Eleanor Waldorf that the pregnancy book she found was actually hers. Once again it seems like Blair is back on top and everything is going her way. Although she is still wearing the princess’s dress, Louis informs his mother that she will be carrying her favorite flowers in the bouquet and that there will be other changes made to the wedding. All seems to be well in the world until the woman fitting Blair reveals her secret: Blair is in fact the one who is pregnant! But who is the father?
The episode comes to an end with the unveiling of Blair’s pregnancy as well as the telltale letter Dan Humphrey receives from a certain someone in Barcelona. Believing that he and Louis were successful in stopping the story from being printed, a check for $10,000 and a note saying, “Congratulations on your first novel!” seems to prove otherwise.
So what’s next for this group of Upper East Siders? Will Serena learn Ivy’s secret? What will come of the relationship between Nate and this mysterious older woman? Will Louis find out about Blair’s pregnancy? Will she run back to the comfort of Humphrey’s arms before the prince gives her the boot? And who is the father of Blair’s baby? One can only hope that these questions will be answered in the weeks to come.