Gossip Girl - Season 3 (2009)

It's Jenny's first day as Queen Bee; A famous actress, Olivia Burke, is assigned as Vanessa's roommate.

Lily and Rufus move up their wedding, but complications threaten to tear them apart; Chuck discovers a secret Carter has been keeping from Serena; Dan and Vanessa are pulled into one of Georgina's schemes.

Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple; Serena and Nate team up to help Carter Baizen.

Serena helps Chuck open his club, but Blair feels left out; Dan is unnerved watching one of Olivia's sex scenes with a former co-star.

Olivia says something she regrets during a talk show appearance and tries to keep Dan from finding out; Nate suspects that his grandfather will stop at nothing to get Trip elected to congress.

Jenny sets her sights on landing the hottest escort for Cotillion. Dan is upset when Olivia (HILARY DUFF) contemplates leaving school. All-girl French band PLASTISCINES performs.

Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa.

Serena is put in an awkward position when Lily invites Tripp and Maureen to join them for dinner; Blair suspects her mother of keeping a big secret; Jenny gets even with Eric in the most cruel way.

Chuck wrestles with a past issue; A serious car accident rocks the Upper East Side; Dan and Vanessa try to navigate their complicated friendship.

Chuck tracks the woman he saw at his father's grave; Jenny agrees to help Damien; Nate and Serena get friendly.

Rufus and Lily grow suspect of Jenny's relationship with Damien. Chuck learns more about the woman who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people.

Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily thinks to tell the secret that she has up till now concealed, but after a call, she changes her mind. Dan and Vanessa explore the new development in their friendship. Chuck is forced to make an extremely difficult decision about his hotel. Meanwhile, Serena and Nate have a fight that is reminiscent of past events.

Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor's fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.

Chuck and Blair are faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage Serenas's efforts. Dan and Vanessa's new relationship hits a bump in the road.

Chuck offers to throw a wedding for a very pregnant Dorota who insists that she and Vanya have a traditional wedding before her parents arrive from Poland and find their daughter pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Serena tells Nate she is having breakfast with the Humphreys when in reality she's secretly meeting up with Carter Baizen. Rufus discovers that Lily has been lying to him about her whereabouts.

When Lily's ex-husband, Dr. William van der Woodsen, shows up unexpectedly in Manhattan, Serena finally gets the reunion she has so desperately wanted with her father, but the circumstances turn out to be far from ideal. When Serena and Nate continue to have relationship issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Meanwhile, Dan finds out that he didn't get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible.

Will's return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and Jenny's relationship is strained as a result of Jenny's deception. Blair spends time on the Columbia campus and realizes where she truly belongs. Dan learns that Vanessa has been keeping yet another secret from him.

When things get tense between Rufus and Will, Serena chooses to stand behind her father, while at the Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimately destroy Lily and Rufus' marriage. After many failed attempts, Chuck makes one last grand gesture to reconcile with Blair, hoping she will finally accept the fact that they are destined to be together.

Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Georgina returns to the Upper East Side...and she has an agenda.