Nate and Serena have spent the summer pretending to be in a relationship to conceal Nate's actual relationship with a married English noblewoman, Catherine Beaton.
Blair and Chuck adjusting to being in a relationship and having to stop the games.
It is revealed that after Nate's father fled the country, the Archibald family's assets were frozen, thus causing the motive for Nate's relationship with Catherine Beaton, who pays him for their encounters.
Nate befriends Dan during a visit to Yale; with their realization of the Archibald's financial problems, Nate is invited to move in with Dan and his family into their Brooklynloft. During this time, Nate and Jenny become attracted to one another, though the two do not enter into a relationship.
Bart Bass seemingly dies, causing Chuck to enter a deep depression and prompting the arrival of Jack Bass. Soon after, Chuck is legally adopted by his stepmother.
Dan and Serena learn their parents, Rufus and Lily, had a love child from their first romance years before.
Georgina returns and appears to have changed her ways; this is soon revealed to be false.
Jenny's ascent the social ladder at Constance causes a rift in her relationship with her family.
After his flirtation with Jenny, Nate enters into a second relationship with Vanessa. After quitting his job at the mayor's office, Nate and Vanessa decide to go backpacking across Europe.
Nate and Serena's relationship - and Jenny trying to stop it.
Chuck's mother returning and giving his hotel to Jack.
Damien and Jenny's relationship/drug dealing and Jenny deciding to wait before sleeping with him.
Eric and Jenny's strained relationship.
Lily and Rufus adjusting to being married and their families living together for the first time.
Blair's constant fight to be top of the College Social Scale and realising NYU is nothing like Constance.
Georgina and Dan starting a relationship.
Olivia coming to NYU trying to get away from the pressures of fame.
Jenny being banished.
Georgina returning pregnant - with Dan's child.
Dan finding out that Milo isn't his.
Dan and Serena trying to work out if they still like each other.
Jenny, Juliet and Vanessa sabotaging Serena.
Blair and Dan kissing and finally admitting their feelings to each other.
William van der Woodsen, Cece, Carol and Charlie come to town to support Lily and have a family picture taken (it's done by all the UES families).
Chuck realizes he wants Blair, tricks Dan Humphrey which leads to Blair not forgiving him.
Serena is suspicious of all the time Dan and Blair are spending together.
Blair and Louis are reunited.
Nate tries to help Raina Thorpe find her mother.
Serena sends a portfolio (with Blair's bad past inside) to Louis' mother to try and ruin their relationship.
Louis' parents disaprove of Blair.
It's revealed that Bart Bass killed Raina's mother, Mrs. Thorpe.
Nate is forced to choose between Raina and Chuck.
Charlie and Vanessa become friends.
Jack Bass comes back to town, and Blair warns Chuck before Jack sees him.
Blair recieves Louis' mother's approval.
Charlie really likes Dan, and takes one of Serena's dresses without permission in an effort to impress him.
Serena and Charlie argue about the dress.
Chuck, Jack and Nate discover that Raina's father, Russell killed Mrs. Thorpe because she was sleeping with Bart Bass.
They blackmail Russell into leaving New York, in return they won't tell Raina what he did.
Nate tells Raina that her father killed her mother, a heartbroken Raina calls her father and cuts her ties with him.
Thinking Chuck told her, Russell returns and lures Blair up to the roof.
It's revealed that Charlie hasn't been taking her medication.
Georgina is back, and is looking for trouble.
Charlie is rejected by Dan when she tries to seduce him because she requested him to call her "Serena".
Chuck saves Blair from Russell.
Chuck and Blair sleep together.
Chuck lets her go, and she goes to Monaco with Louis for the summer.
Serena takes a new writing job in California.
Vanessa moves to Spain, and takes Dan's story and gives it to a publisher.
Rufus spends the summer with Lily, who is still under house arrest.
Dan spends his summer in the Hamptons, with Eric.
Charlie returns to Miami, but it's revealed that her real name is Ivy, and she was hired to play Charlie by Carol, to protect her daughter. She g ives the checkbooks to Charlie's trustfund back - but secretly keeps some in her purse.
We see Dorota emptying a trash can with a positive pregnancy test in it, the question is - is the baby Louis' or Chuck's?
Louis discovers that Blair had thought the baby might be Chuck's, Blair tells Chuck that the baby isn't his and that she is preparing for a life with her baby's father.
Serena finds out that Dan loves Blair, just after she realises she loves Dan.
Oblivious to the affections Dan holds for her, Blair tries to decide between Louis and Chuck. Eventually choosing Chuck they end up in a car accident caused by Tripp Vanderbilt who meant for Nate to be in that particular car.
Blair finds out she has lost her baby and that Chuck is close to dying as well. Making a pact with God she says she will marry Louis if he keeps Chuck alive, moments later a nurse tells Blair that Chuck is awake.
During her wedding proceedings Blair becomes even closer to Dan.
Footage of Blair confessing her love to Chuck straight before her wedding is aired just as everyone is asked if they have any objections. The video was sent in by Dan trying to stop Blair from going through with it.
Louis is forcing Blair to live a year as his 'wife' because he cannot forgive her for what she did to him but doesn't want their marriage to look false.
Georgina is revealed to have taken over GG since the car accident which Blair and Chuck almost died in.
Dan kisses Blair again, this time they are only stopped when a furious Serena catches them. Georgina has the moment on film, ready for the perfect moment to out the couple.