10 'Gossip Girl' Moments to Talk About

Nate and Serena's Scintillating Hookup

In season one, Blair Waldorf's (Leighton Meester) boyfriend, Nate Archibald (Chace Crawford), has a steamy one-night stand with with Blair's best friend, Serena Van der Woodsen (Blake Lively) after a wedding. It was a secret until Nate decided to tell Blair that he's always had feelings for Serena.

Serena Accidentally Kills Someone

Serena reveals to pals a deep dark secret in season two. After a drug-fueled night, Serena was secretly caught on tape witnessing a drug overdose and leaving the scene. After the incident, Serena escaped to boarding school.

Chuck and Blair's Limo Love

Blair spends the night seducing Chuck at his nightclub, and the two finally hookup in a limo on their way home.

Chuck Finally Tells Blair He Loves Her!

The moment fans waited all of season two to see: Chuck Bass (Ed Westwick) finally professes his love to Blair Waldorf.

Rufus and Lily's Secret Lovechild

Right when Lily Van der Woodsen (Kelly Rutherford) and Rufus Humphrey (Matthew Settle) were about to tie the knot after their long love affair, they found out that their child they gave up for adoption at birth didn't die after all!

Three's Company - Or Is It?

In one of the most risque scenes in CW history, Dan Humphrey (Penn Badgley), Vanessa Abrams (Jessica Szohr) and season guest star Olivia (Hilary Duff) engaged in a threesome, that turned out to be a drama-filled mess!

Baby on Board

"Gossip Girl" villain Georgina Sparks (Michelle Trachtenberg) returned during the season three finale to announce she was carrying Dan's baby!

Sleeping with the Enemy

Jenny Humphrey (Taylor Momsen) loses her virginity to Chuck Bass in season three. Chuck tried to rape Jenny in the first season of "Gossip Girl."

Playing with Fire

Jenny Humphrey begins dating handsome drug-dealer Damien (Kevin Zegers), which puts her in hot water when she starts dealing drugs with him.

Gunned Down

During the final moments of the "Gossip Girl" season three finale, Chuck Bass is shot when thieves try to steal the engagement ring he bought for Blair. Chuck never had the chance to pop the question because Blair found out he slept with Jenny beforehand.