Timeline of Gossip Girl

The Gossip Girl timeline chronicles the significant events of Gossip Girl during its entire six season run, from Pilot to New York, I Love You XOXO.

Timeline

Serena van der Woodsen returns to New York's Upper East side and begins a relationship with Dan Humphrey.
There is a love triangle between Blair Waldorf, Nate Archibald, and Serena.
There is a love triangle between Nate, Blair, and Chuck Bass.
Serena's little brother, Eric van der Woodsen is released from rehab after being treated for depression after his suicide attempt. It's revealed he's also gay.
Jenny Humphrey, Dan's little sister, struggles to be accepted by Blair and her friends.
Dan's best friend Vanessa Abrams suddenly turns up and causes some struggles in the relationship between Dan and Serena.
Dan and Serena have troubles with Georgina Sparks, a frenemy from Serena's past.
Lily van der Woodsen plans to marry Bart Bass, Chuck's father, but is forced to deal with her lingering feelings for Rufus Humphrey, Dan's dad.

The newly created Bass-van der Woodsen family, known as the wealthiest on the Upper East Side, struggle with their ups and downs.
The marriage of Eleanor Waldorf and Cyrus Rose, causing Blair to struggle with her new blended family.
Jenny's rebellion from "Little J" and attempting to start her own clothing line.
Dan is accepted to Yale, but has to refuse due to financial stress and ends up at NYU along with Vanessa. Serena is also accepted, but denies to attend Brown University. Blair is rejected by Yale, but is able to get into NYU with Cyrus' help. Nate plans to attend Columbia University.
Nate accepts money from a married Duchess, Catherine Beaton, to save his family from debt.
Bart tragically dies in a car accident. Rufus and Lily rekindle their relationship after his death.
Lily adopts Chuck, becoming his legal guardian, so that she could be named head of Bass Industries and give it to Chuck when he is of age.
Serena, Eric, Dan, and Jenny discover Lily and Rufus had a lovechild and they are related through their unknown half-brother.
Blair and Chuck struggle with admitting their feelings for one another.

Chuck and Blair are in an official relationship, but wonder whether it will work out without games.
Vanessa's new friend Scott Rosson arrives and has a secret to share.
Serena defers Brown and tries to find ways to make herself useful in Manhattan.
Chuck purchases The Empire Hotel.
Blair and Serena try to figure out their friendship as they grow and mature.
Nate and Serena and Dan and Vanessa begin dating but find that dating your best friend isn't without its complications.
Dorota and Vanya get married and have a daughter, Anastasia. Meanwhile, Eleanor and Cyrus move to Paris full time.
Serena's father William arrives back in town and reveals a secret about Lily.
Blair and Chuck separate, after he commits two unforgivable acts.

Blair and Chuck struggle with an on again/off again relationship, that gets thrown for a curve when love interests for both come into the picture.
Dan becomes a father for a short period when Georgina leaves her son, Milo, with him.
Blair and Serena begin at Columbia but face challenges at their new school.
Nate begins dating Juliet Sharp, a girl with a mysterious vendetta against Serena.
Lily tries to sell Bass Industries, but the Bass family is in for a shock when an old enemy, Russell Thorpe and his daughter Raina come to town.
After keeping it secret for so long, Lily serves a house arrest sentence for forging Serena's signature on a legal document.
Serena's cousin Charlie Rhodes comes to Manhattan; but is she who she says she is?
Blair becomes engaged to Prince Louis Grimaldi and is on the fast track to achieving her ultimate goal: becoming a princess.

The season premiere (Yes, Then Zero) is set in Los Angeles, California, where Serena has a job on a film set.
Nate begins an affair with Diana Payne, an older woman who has many secrets, and begins working at The NY Spectator. Ivy, still posing as Charlie, also works there.
Dan's first book, Inside, is published.
Blair is pregnant with Louis' baby but ultimately loses it. The two get married, then divorced.
Dan and Blair begin a romantic relationship.
Charlie's real identity is revealed to everyone, as is who put her up to it and why.
Gossip Girl's identity is revealed: but is it the real one?
The van der Woodsen/Rhodes family dynamic changes after a shocking revelation is made, surrounding the real Charlie, Lola Rhodes and the death of another family member.
Everyone is rocked by the return of Bart Bass to the Upper East Side.

Blair and Serena seek to deal with the biggest roadblock in their friendship ever.
Blair and Chuck try to achieve success on their own before they can finally be together.
Nate struggles to keep The NY Spectator afloat.
Ivy tries to bring down Lily with an unlikely ally.
Chuck tries to take down his father, newly resurrected Bart Bass, and Blair tries to become a successful CEO at Waldorf Designs.
The identity of Gossip Girl is finally revealed; as is what happens to everyone after a time jump.