Five years ago today on September 19, 2007, Gossip Girl was brought to life on The CW. The pilot episode, which aired that evening, was the beginning of the Upper East Side obsession for many of us. Let’s raise a glass to the show and check out some of our fave moments from the episode that started it all:
- Serena’s return to New York – The episode opens as Serena van der Woodsen has been spotted at Grand Central Station, apparently returning from boarding school in Connecticut. No one knows why she left and know one knows why she came back. All we know is that it’s about to get juicy.
- Blair and Serena reunite – And it’s not pretty. Blair Waldorf is obviously mad at S when she sees her at the party. Then later on in the episode, Blair doesn’t invite Serena to her Kiss on the Lips party. The two finally go to drinks and (kind of) make up.
- Nate and Serena reunite – There’s a look between S and Nate Archibald at the party they see each other at. B notices it too. The next day Nate is standing outside the Palace (where Serena and her family are staying while their apartment undergoes renovation). He tries to talk to her, but she says, “I didn’t come back for you.”
- Chuck outs Serena for sleeping with Nate – Chuck Bass tries to have sex with S. As his (unsuccessful) attempt is going down, he tells her he knows why she left for boarding school — because she and Nate had sex at a wedding. Meanwhile, Nate is confessing this to Blair and she gets very upset (obvi).
- Serena and Dan go on a date – Dan Humphrey and Serena run into each other at the Palace (he saves her phone) and set up a date for that night to go watch his dad’s band play and end up rescuing Dan’s sister Jenny from Chuck Bass at the Kiss on the Lips party. Dan punches Chuck, who swears revenge (he does know all the dirt on Serena after all…)
The episode is a classic must-see (over and over again). What was your favorite moment from it? Tell us in a comment below!
PS- Style has off-network rights to run Gossip Girl on their network, so you can catch your favorite classic episodes every Wednesday night from 8-11 pm!

I watched hole tv series again this year and I feel in love with Gossip Girl again. Gossip Girl is my life and I don’t know what I’m gonna do with out Gossip Girl…:(
I Know Right , But Happy Anniversary Gossip Girl .! ( I Know Im Late )
My favorite moment was when Serena leaves the party with Dan.. that was such a Upper East Side moment
Happy Anniversary GG..!!!!!!!! Love ya!!! XOXO
Im watching gossip girl on netflix starting with season 1,im loving it wished I watched it sooner. Was sry to hear show was ending after the next season. Great show
i totally love gossip girl,i have always loved gg and i will always love gg!!♥♥♥♥