Dr. Estrangeloved
When Lily’s ex-husband, Dr. William van der Woodsen , shows up unexpectedly in Manhattan, Serena finally gets the reunion she has so desperately wanted with her father, but the circumstances turn out to be far from ideal. When Serena and Nate continue to have relationship issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Meanwhile, Dan finds out that he didn’t get accepted into the Tisch writing program and Vanessa (J admits she may have been somewhat responsible.Source: The CW
Chuck, wanting his best friend back, plans with Jenny to break Serena and Nate up. Meanwhile, Serena’s father, Dr. William van der Woodsen, returns.
Lily van der Woodsen (Kelly Rutherford) tells Rufus Humphrey (Matthew Settle) the truth about where she has been. She has been getting treated for cancer by her ex-husband William (Billy Baldwin). He reveals that the cancer has returned and that he has come to continue the treatment. This makes Rufus jealous.
Serena van der Woodsen (Blake Lively) is overwhelmed to have her father back in the picture, and does not know what to think. On her way out, she bumps into Jenny Humphrey (Taylor Momsen) who had passed out at Nate Archibald (Chace Crawford’s) apartment the night before. Taking Chuck Bass (Ed Westwick’s) advice, Jenny plants one of Nate’s shirts in her purse for Serena to see. Jenny is trying to steal Nate away from Serena. Serena sees the shirt and is angry at Nate, and doesn’t tell him about her mom.
Vanessa Abrhams (Jessica Szohr) earned admission to a writing program that Dan Humphrey (Penn Badgley) was rejected from. Dan and Vanessa attend an art party in Brooklyn that Chuck, Nate, Jenny, and Blair Waldorf (Leighton Meester) go to as well. Chuck brings Nate there to help cheer him up about Serena, inviting Jenny along in hopes of them getting together which would mean Nate and Serena would break up, and Chuck would get more time with his best friend Nate. Blair was at the party to find a new man. She had planned a party with eligible bachelors for herself, which Chuck sabotaged.
Dan and Vanessa end up getting into an argument. Vanessa does not believe that Dan is happy for her getting into this program. Blair and Chuck continue to try and make each other jealous, but eventually Blair realizes that she needs to face the situation and not try to distract herself from it. She allows herself to feel sad about her heartbreak. Serena walks in on Jenny throwing herself at Nate. Serena is furious and Nate asks Jenny to leave. Serena and Nate clear things up and Serena tells Nate about her mother’s illness.
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