Episode 19 – Dr. Estrangeloved
Date Aired April 26th, 2010Serena’s father (William Baldwin) visits Manhattan unexpectedly; Nate and Serena continue to have relationship issues; Dan gets upsetting news.




Serena’s father (William Baldwin) visits Manhattan unexpectedly; Nate and Serena continue to have relationship issues; Dan gets upsetting news.
Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman he saw at his father’s grave. Jenny agrees to accompany Damien to a State Dinner but is unaware that he...
On the anniversary of Bart Bass death, Chuck has to deal with some issues from the past and a car accident disturbs the Upper East Side. Meanwhile, Dan and Vanessa tried to stay in their complicated friendship no matter what. Jenny is accused of beating...
Blair bid to find out what her Mother is hiding backfires. Vanessa gets into a fight with her mom and ends up at the Humphreys. Rufus is hurt when he discovers Lily has been lying to him. Chuck divulges some news that could ruin a friend to Nate. Jenny...
Trying to impress NYU theater kids, Blair uses her contacts to get a private concert with today’s hottest performer, Lady Gaga. Dan and Olivia sign up to write and star in an NYU play, based on an idea by Blair and directed by Vanessa. Meanwhile,...
Jenny wants to be the Queen Bee of not only Constance but of all the Upper East Side, as she lands the hottest escort for the Cotillion. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the “true college experience”....
Olivia, as a guest on Jimmy Fallon’s talk show, says something she regrets and tries to hide it from Dan. With elections coming up, Nate suspects his grandfather will do everything he has to get Trip into congress. After another fight with Serena,...
Looking for publicity for his new hotel, Chuck moves his club’s opening and convinces Serena to assist him in getting the word out. Feeling left out, Blair tries to win Chuck’s approval by secretly helping him with a problem concerning the...
Vanessa desperately trying to have her mom’s approval, teams up with Blair to do the honor of delivering the freshman toast at NYU, but what will be the price she has to pay? Dan takes Olivia to meet Rufus and Lily, which leads to all sorts of problems...
Lily and Rufus move up their wedding day, but someone or something will come between them. Can they overcome this and finally get married? Chuck uncovers Carter’s secret. Georgina traps Dan and Vanessa into one of her schemes. Blair suspect something...
It’s Jenny’s first day of school at Constance Billard which means it’s her time to take her place as the new Queen Bee. But Blair wants to take her spotlight when she is needed back at Constance. Lily returns home to find that everything...
It’s a face-off between Chuck and Blair when they both want to bid on the same item at Sotheby’s. Meanwhile, Serena suspects that Carter may have return to his old habits, while Georgina takes an interest in Dan, and Vanessa suspect something...
Blair ends up with Georgina as as her roommate in the dorms at NYU. While Serena and Chuck come to blows, so she joins forces with Chuck’s enemy, Carter. Nate and Bree try to take their relationship up a gear despite the animosity between their...
As the summer ends, Blair and Chuck are madly in love and adjusting to their new “in a relationship” status, breaking all traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide...