Season 5

Kaylee DeFer plays a character named Ivy who is being paid by Lily's sister, Carol, to impersonate her daughter, Serena’s cousin Charlie Rhodes.  The season began in Los Angeles when a re-energized Chuck and Nate decided to pay Serena a visit. Chuck had a new found philosophy and says "yes" to everything, even death defying stunts. Serena continues to work on the movie set, and is offered a full-time job at the end of the episode. Nate begins an affair with an older woman. Who may have a hidden reason for being with Nate?  Back in New York, Dan learns that Vanessa has published one chapter of his novel, and Blair continues to plan her wedding to Louis, and she also learns she is pregnant.

Later in the season Blair finds out the baby might not be Louis, but sadly she loses the baby. A few days before the wedding Chuck and Blair were in a car accident and that made Blair realize how much she actually loved Chuck, but she knew she couldn’t be with him due to her engagement with Louis. Blair started going to church with Dan and made a promise to God that she would not see Chuck as long as Chuck would not get hurt. Rumors went around that Blair and Dan were more than friends but later were proven wrong.

The Run away Bride

Before Blair’s wedding she admitted the feelings she had for Chuck but explained she could not be with him due to her promise to God, Georgia got it all on video and someone showed it on the big screen during the wedding. Blair explained to Louis that it was not true and he ‘forgave’ her and they then got married. During the reception of the wedding Louis admitted to Blair he does not forgive her and that they are only a happy couple in public and behind closed doors they are nothing and that it will carry on till he says it’s enough. Blair left the wedding early and went to the airport with Dan, she wanted to get a divorce with Louis, due to not having her passport she could not leave the county. So she returned to Louis for the reason that if she didn’t her family would have to pay a massive amount of money which they do not have, Chuck offered to pay the money but Blair rejected and said it was her responsibility to marry Louis.
Valentine’s Day didn’t go to good…
Serena spent her Valentine’s Day waiting for Dan, who Blair set her up with.
Nate threw a party to try get the cater waiter to come, which he has a crush on.
Ivy and Charlie met each other at the party and started talking…

Blair spends her Valentines without Louis, and finds out Louis had organized a social event manager for her. Blair goes to Nate’s party and ends up kissing Dan, Georgia gets a picture of the kiss and Serena walked in on them as they kissed.
Georgia showed Chuck the picture, which made Chuck give up on Blair so he spent his night with a girl he met at the bar and Georgia admitted to Dan that she is Gossip Girl.

Charlie  and Ivy

Serena’s grandma goes to hospital and soon dies of a stroke. The secrete of Ivy being Charlie is relisted, when the real Charlie comes to the hospital to be with her Grandma and she sees Ivy with her mother. Charlie’s mother used Ivy to get money out of Charlie’s trust fund and Charlie stays by Nate for the night and  Blair admits to Dan that she has feelings for him.