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.

Chuck offers to throw Dorota’s wedding before Dorota’s parent’s arrive from Poland and see her pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Meanwhile, Serena lies to Nate telling him she’s having breakfast...

Chuck and Blair’s relationship is faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny tries to sabotage her. Meanwhile, Dan and Vanessa’s relationship hits a bump in the road.

Jack Bass is back in NY and Chuck finds himself at odds with his uncle. Eleanor puts Blair in charge of making sure her fashion show is a huge success with an important client. Rufus tries to get Jenny to be more good by volunteering to help in Eleanor’s fashion show, but it takes a turn for the...

Despite being grounded, Jenny continues to see Damien who pressures her to sleep with him. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s very risky. Meanwhile, Dan and Vanessa explore the new stage of their friendship, while Chuck is forced to make a very...

Rufus and Lily suspect something bad about Jenny’s and Damien’s relationship. Chuck learns more about the woman at the cemetery who may or may not be his mother. Meanwhile, Dan and Vanessa struggle with the awkwardness of dating other people.

Nate and Serena explore their friendship. Blair thinks Chuck is having problems forgetting the woman he saw at his father’s grave. Jenny go with Damien to a State Dinner but she wasn’t aware that it was also to help him with a drug exchange. Vanessa and Dan try to move past Dan’s confession....

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 a classmate, and Eric has to decide which story...

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 finds tries to get even with Eric after learning...

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, Serena turns to Nate for help in a dificult situation,...

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”. Leighton Meester’s new single “Somebody...

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, Blair gets a new friend and takes her to an election...

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 opening night. Meanwhile, Dan get’s nervous...

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 for the new couple. Meanwhile, Serena and...

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 not good about Bree and shares her concerns...

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 is different now. Meanwhile, a famous movie actress,...

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 is not right with Scott.

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 families.

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 and a complicated relationship with Carter Baizen....