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This plan entails having Rufus crash Jenny's lunch with Nate to ground her, which works until he decides to attend an event to see Lily. Having never seen the letter, Jenny believes Nate lost interest in her and moved on.

Well, it'll only stop when you stop it. Knowing almost everyone is ignoring him, Jenny uses this opportunity to spend some alone time with Nate and they go to lunch together. At the end of the series, Nate leaves to sail around the world to avoid ruining Blair and Serena's friendship.

Dating History

Meanwhile, Jenny has recently quit working at Waldorf Designs and set out to start her own clothing line. At the end of the night, she trades masks and shrugs with Serena van der Woodsen and is grabbed by Nate, thinking she's Serena. During the third seasonJenny continues to crush on Nate despite him dating her stepsister, Serena van der Woodsen.

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The day of, Serena lies to Nate that she is having breakfast with her family when she is actually meeting Nate's enemy, Carter Baizenwho has information on her absent father. However, Damien wants to have sex with Jenny, but she is unsure about losing her virginity to him.

When Nate sees the blast, he assumes it's false until a vengeful Jenny confirms the rumor.

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However, Nate is uninterested and rejects her advances. He slowly stops talking to her and she jenny rylance relationships dating it's over when she sees him with Blair at a party he stood her up to attend. Angry, she kicks Carter out of the car and calls Nate's phone, which Jenny answers.

Once Jenny's plan takes place, it ultimately backfires: When Serena discovers that she is planning on doing it, she plots with Nate to stop Jenny from doing so.

Jennie Rylance

Furious, Blair fires Jenny and she and Nate break up that evening after she explains that she knows what he did. She confronts Nate about it and they start fighting about who is keeping secrets from who.

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Jenny pulls away and runs off right before the real Serena comes to tell Nate to look for Blair Waldorf. She makes a dress for her with no lining that will reveal her underwear and bra in front of everyone and the plan works.

He tells Jenny about the letter himself, and says he isn't interested in her anymore after what she did It's a Wonderful Lie. That night, Nate agrees to go to a Brooklyn art party with Chuck and Jenny, but Serena gets upset when she realizes where he is.

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The game eventually ends up with Jenny and Nate as the final players and in order to win, Jenny kisses him. Serena asks her to tell him that she's leaving but does't want any more secrets, and that she loves him. Concerned, Nate finds Jenny's brother, Dan Humphreyand fills him in on her request.

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She also attempts to make him late for the party, which works for a time until they do arrive after a Gossip Girl alert is issued. As a result, Nate breaks up with Blair, who eventually learns it was Jenny who told him.

When she realizes Serena has entered the room she tries to kiss him but he refuses. Her first step is to find investors and she plans to crash an event at The Palace Hotel where many UES socialites will be and stage a guerrilla fashion show.

Jenny Rylance

Before the plan takes place, the guilt of stealing the letter convinces Vanessa to tell Nate she stole the letter and accept the consequences. At the show, Agnes drugs Jenny and leaves her at a bachelor party, which Nate witnesses her being taken to.

Offended, she does so. In the The Blair Bitch ProjectNate notices the change in Jenny's attitude after Blair is dethroned as queen and she's cemented as one of the girls of the steps. While living there he becomes closer friends with Jenny and develops a small crush on her, that he acts on in Pret-a-Poor-J after he finds her taking photos in her bra with her friend Agnes Andrews.

Serena confronts them both and reveals that she tried to call him at the wedding and that Jenny failed to pass on her message.