Skandal Öpüşme Partisi sonrasında, Serena en iyi dostu Blair tarafından oldukça soğuk karşılanır.

Blair, Serena hakkında uzun süre sır olarak kalması mümkün olmayan skandal bilgileri açığa çıkarır.

Çocukluk arkadaşı Vanessa geri dönüp ona olan hislerini açıklayınca, Dan iki kız arasında kalıverir.

Serena ve Dan, tamamen farklı dünyaların insanları olmalarına rağmen birbirleri için yanıp tutuştuklarını en sonunda kabul ederler.

Blair'in babası tatil için eve beklenmedik bir misafirle, erkek arkadaşıyla gelir; Blair'in hayal kırıklığını saklaması ise hiç kolay olmaz.

Serena ve arkadaşları eğlenceli bir gece geçirmek için gizlice okulun havuzuna girer.

Blair, Kraliçe Arı unvanını kaybettikten sonra okula döner; Serena ise gelecekteki üvey erkek kardeşi Chuck ile yaşamaktan hiç hoşlanmaz.

Georgina, Serena'nın Manhattan'dan yatılı okula gitmek için kaçmasının asıl nedenini ortaya çıkarır ve Serena, hızlı bir şekilde eski alışkanlıklarına geri döner.

Serena'nın saygınlığı söz konusu olunca, Blair manipülatif Georgina'yla baş etmek için ipleri eline alır.

Blair, annesinin Moda Haftasındaki gösterisini sabote eder. Dan, Chuck'la takılmaya başlar ve karanlık tarafa geçmenin her zaman riskli olduğunu öğrenir.

Blair, Chuck'ı Vanessa'yı baştan çıkartması için kışkırtarak intikam almaya çalışır. Serena, Lily'nin partisinde baş kaldırır. Dan ve Jenny, Nate'in bir sırrını öğrenir.

Serena, Aaron'ın ondan bir sır sakladığını fark eder. Jenny ve Agnes, bir gerilla moda gösterisi planlar. Blair, bir Yale bağışçısının kızına bakıcılık yapar.

Dan, bir makale yazmak için Bart Bass'e yakınlaşmaya çalışır; fakat Chuck bunu öğrenince işler kızışır.

Annesinin yeni erkek arkadaşı, Blair'in en sevdiği Şükran Günü geleneklerini mahveder. Serena, Aaron'a geçmişinden bahsetmez... Fakat bunu yapan Dan olacaktır.

Her sene yapılan Kar Tanesi Balosu'nda, Blair ve Chuck birbirleri için ideal flörtleri bulabilecekleri konusunda iddiaya girer.

Ani ve trajik bir olay, başta Chuck ve van der Woodsen ailesi olmak üzere, Yukarı Doğu Yakası'ndaki herkesin hayatına etki eder.

On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma.

Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.

Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne.

When Gossip Girl goes after Blair as she’s never done before, Serena admits she may have unintentionally played an important role in Blair’s latest nightmare. Meanwhile, Nate invites Lola to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode’s end, Blair will make a choice between the two men in her life…will it be Chuck or will it be Dan?

After a brief encounter abroad, Chuck and Blair make a promise to each other about their relationship, which leaves them once again apart. Dan, with some help from an unlikely ally, Georgina, is writing a scathing tell-all book that can only mean trouble. As the sole head of The Spectator, Nate is making his own decisions and is ready to go up against Gossip Girl. As word spreads that Serena is missing, the gang bands together to find her and are shocked by what they find.

Trying to prove herself in adult society, Serena hosts the Central Park Conservancy’s big gala, of which she is now the newest Board Member, and she and Nate both learn something shocking about their significant others. Blair prepares to debut her new fashion line, but a rival from her past holds the key to her future. With the help of Georgina, Dan lands some meetings with publishers, but he must decide if he is willing to sacrifice his integrity in order to get his work published. Meanwhile, Chuck tries to persuade Amira to help him look into his father’s past, even if it means jeopardizing Lily and Bart’s relationship.

Chuck’s continued investigation into his father’s dealings leads him to an unlikely event with Manhattan’s elite, where he hopes to find the one person who can tell him the truth about Bart. Serena and Steven decide to reveal their romantic histories so they aren’t surprised by anything, but neither was prepared for what they uncovered. With The Spectator in jeopardy after Dan decided to publish elsewhere, Nate must make a difficult decision to keep it in business. Meanwhile, Georgina pushes Dan to choose a worthy person to date to boost his image, but he finds himself drawn in a different direction.

After Eleanor gives Blair an ultimatum, Blair is even more determined to remedy Waldorf Designs’ problems by making a splash with a dress at the upcoming Cotillion, but a shocking revelation at the ball affects everyone. Serena becomes worried about Steven’s attitude toward her, but after some investigating she discovers the surprising reason why. Chuck finds an unlikely ally as he tries to drive a wedge between Bart and Lily’s relationship to help expose his father’s secret. Meanwhile, Dan publishes another article, but the effect is just the opposite of what he was hoping for.

Serena and Dan realize that they need to make amends with the people they have wronged. Chuck’s search for evidence of his father’s illegal activities leads him to a showdown with Bart.

Serena and Dan decide to throw their first Thanksgiving together, inviting only their closest friends, but everyone seems to have their own agenda for attending. Feeling defeated by his father, Chuck begins a downward spiral, leaving Blair to find a solution to his problems. Meanwhile, Dan has written his latest exposé, but he must make a tough decision whether to publish it, knowing it could destroy a close friendship.

After a run-in with an increasingly paranoid Bart, Blair grows alarmingly concerned for Chuck’s safety. However, feeling confident that his father will never hurt him, Chuck makes a deal that could change his life. Wanting to make things better for Chuck, Blair devises a plan with the help of Serena, Georgina and Sage to try and get what they need out of Bart. Meanwhile, Nate's financial dilemma finally lands him in a place that he never thought he would be.