The first episode of the second season is set in hemp and called "Summer, Kind of Wonderful", a product of John Hughes' film "Some Kind of Wonderful." Premiere aired on CW on September 1st with 3.4 million viewers, a impressive numbers for the CW Network. Season 2 is set to have 25 episodes total. It was also announced that the OC alum Willa Holland will be reteaming with Josh Schwartz to star in three or more episodes of Season 2, playing Agnes, a 16-year-old model working for Eleanor Waldorf. John Patrick Amedori was also cast as Aaron Rose, Serena van der Woodsen new love interest.
The season starts with the first episode of hemp's, wrapping his summer. Serena and Nate had spent the summer seen together since Serena had told him at the end of Season One, that if he wanted to, they could be alone together in the summer. The two lead a "late" relationship as another character, Catherine Mason Mädchen Amick plays, inserted at the beginning of the season. She is an older woman who seduces Nate. She is married and has an affair with Nate over the summer while they are spending time hemp is on summer break. Serena and Nate seems to be together as a cover for Nate's affair with Catherine. Serena helps Nate blackout his affair with Catherine with some reluctance, because she believes it is dangerous and stupid, but she looks back, she acknowledges that she also made it dangerous and stupid things in the past and can not judge Nate. Serena stops helping Nate anyway, in honor of their friendship and their history together. Catherine is also the stepmother of Blair Waldorf new love interest, Marcus (guest star Patrick Heusinger). Although Blair is now with Marcus, who is revealed as a rich English Lord, Chuck sorry to lose her over the summer, trying to win her heart back. He is friends with Marcus to go to Blair. Serena and Nate kiss caught on the White Party by Dan creates more conflict. Serena and Dan decide to get back together. Serena wants to keep it a secret, but eventually all find out through Gossip Girl.
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In a city in the whole blackout Blair "wrong" is close to having sex with Chuck to meet her needs, Marcus, is to deprive her. When the light comes on again, Marcus walks on Blair and Chuck. He goes to punch Chuck and storms out of the room. Blair quickly follows says that he is a she wants and not Chuck. Marcus accuses her only wish him the title, but he wants her too. Blair then asks him to prove it, and they are seen making out on the steps of Blair's home.
In the meantime, under blackout, Serena and Dan get stuck in the lift on the way to Blair's party. It will have to discuss the reasons they broke up in the first place. They decide that they can not continue the relationship and break up again. Nate is still a secret involved with Catherine but have a hard time juggling his tryst with her and renew his relationship with Vanessa. When Catherine learns of it she orders Vanessa to steer clear from Nate or she will go forward with information about Nate father's residence to the FBI. Vanessa back off, to protect Nate but soon learns that Catherine has been involved with Marcus too. Rather than go to Nate, she confides in Dan and Blair. Blair composers a plan to blackmail Catherine on paying off debt Nate far, but it back fires once Vanessa out of the wound show that Catherine's husband about her infidelity.
For the first week of his earlier years at school, Dan and Serena avoid each other before Serena sees Dan talking to the new girl, Amanda (guest star Laura-Leigh). Blair and her minions quickly come to the rescue, invite Amanda to lunch, and leaving Dan without lunch friend symbol for the day. Later that night Lily comes to the loft with a bottle of wine and a DVD that she is lonely. Rufus straightforwardly say that they can not be friends while you're talking his girlfriend walks in the door. Lily looks hurt and leaves, which gives him the bottle of wine.
With Fashion week in the horizon, Blair knows that she can regain his throne by helping her henchmen to comment on Eleanor's show. Blair soon discovers that not only is Serena in the radar with her new socialites friend Poppy Lifton (guest star Tamara Feldman), but Jenny is the bright star at Eleanor's studio. Jenny has not only changed the seating capacity chart that Blair has been developed, but she has received much attention for their work. Blair soon decides to sabotage the show by sending models at home (as Jenny saves by having socialites friends Poppy and Serena model to show), and even Serena sends down the runway in a dress that Jenny made. As expected, Eleanor is furious to find Jenny's dress on the runway, but Blair soon clear Jenny is not the enemy, stepping up for her. Eleanor receives rave reviews for Jenny's dress. Serena and Blair have an altercation, which can best be described as a "hold me back, I want to be everything I am", that Blair is not amused. Tensions are high, when Blair sees photographers to take pictures of Poppy and Serena when they leave the show. A subplot of this episode finds Dan attempting to experience life in Chuck's shoes, leads him to discover a dark secret about Chuck and Bart conditions. Lily also unearths that Bart has gone far to make nothing from their past could destroy the family, which contains a file on Lily before her life again as an Upper East Side mother. Rufus and Jenny are also out because of Jenny's refusal to go to school. She will focus on her talent as a designer, much to Rufus' Chagrin.
Jenny is disagreement with Rufus finally ended when he agrees to spend a day with her at Eleanor's studio before making the final call on her to return to school on Monday. A so-called accidental run in with Lily causes single dad to realize that he should let his daughter follow her dreams, because even though he could not follow his, they are now within reach for Jenny. With the help of Vanessa, she decides to be home-schooled. In the meantime, Blair, Serena, Dan, Nate and Chuck visits Yale University to give them a taste of college life there. While Serena was originally planned to visit Brown University, she ditches plan to get even with Blair on the impressive Dean of Yale so much that he invites her to an intimate gathering at his house. In a rage, Blair manipulates her way to dinner and the evening ends in a girl-on-girl catfight between the two best friends. Chuck, Dan and Nate all get in trouble with Dan discovers that none of his recommendation letters were never sent, Nate will head hunted because of his father's actions and Chuck is kidnapped by a group of skull and bones members who want to use him to get even with the Archibald family.
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