Jenny is sleeping on Agnes’ couch and searching for a manager to make her fashion dreams happen. Rufus pretends to be cool about that, and is also attempting to support Dan’s new decision to write about Chuck to score a recommendation letter to Yale.
Blair and her cronies are attempting to plan her 18th birthday party. But it is Eleanor’s new boyfriend, Cyrus, who Blair is dying to meet, that ends up dominating the conversation. Serena, meanwhile, keeps getting distracted by lovey text messages from Aaron and bails to go meet him.
Text messages from Aaron lead our girl Serena to Times Square, where she gets a message that tells her to “Look Up.” She sees herself on the huge Jumbotron and is giddy with excitement. Aaron shows up behind her and they broadcast a kiss over all the people and traffic. Serena is smitten and agrees to pose for him in his studio.
Dan meets with his mentor, Noah Shapiro, along with the editor of New York Magazine. Having figured out that Charlie Trout is Chuck Bass, son of Bart Bass, two older men convince Dan to write an expose on the man behind Bass Industries. They want him to dig up dirt on Bart.
If he comes up with a story, his work will be printed in New York Magazine with more assignments to follow. Dan says he can’t pass up the opportunity and goes to talk to Bart, feigning interest in the construction business.
Bart says that he will allow Dan to shadow him two days a week, but Chuck is extremely suspicious of the situation. Chuck eventually sees Dan with Noah Shapiro and calls a friend at New York Magazine to get the details.
Earlier, Chuck surprised his father with season tickets to see the Rangers, but Bart blew him off and told his son that he’s too busy. Still, Chuck is working like a madman to get to the bottom of whatever Dan's up to.
Eleanor is too busy to pay attention to Blair as well. Instead of attending Blair’s party, Eleanor decides she is going to go to see Cyndi Lauper with Cyrus - who is the opposite of what Blair expected. Short, loud, not that proper or concerned with some of the things she is.
In other words, it's not long before Blair decides to scheme and dig up some dirt on him. She asks him to lunch where he confides in her about why he and his first wife divorced - he fell in love with a woman he met when he was in the Vietnam War. The woman later died, but the love he felt for her has never been equaled until Eleanor.
On the hunt for a manager, Jenny and Agnes bicker during a business meeting and Jenny flips out. Displeased with her lack of progress, Jenny decides to take matters into her own hands and calls up Scott Smith, one of the people who rejected them, and tells him she's ditched Agnes and wants in.
Smith says that he would be happy to represent Jenny without Agnes, and just needs a parent’s signature on the paperwork since she isn’t 18.
Serena heads to Aaron’s studio and is all excited and ready to be his muse for the day. The following day, Serena is excited to see the pics he took transformed into some sort of installation and seems to be falling for him when they are interrupted by a girl named Danielle who shows up at Aaron’s studio for a photo shoot.
Dan gets a tip from a source who says that he has dirt on Bart Bass. Dan meets a scruffy guy in an alley who tells him about how Bart torched a building so that he could collect the insurance money in the 1980s.
When Dan confronts him about the building, Bart mentions a death and says he’s been haunted by it ever since. Dan is shocked to hear somebody died, but before he can find out more, Chuck steps in and tells his Dad not to zip it - Dan is writing a piece for a magazine.
Bart attempts to bribe Dan to kill the story. Dan goes to leave, but Chuck catches up with him and warns him against using the material - it will destroy his family and he practically begs Dan to do the right thing.
Dan’s conscious gets the best of him and he decides not to publish it - but he does mail the short story about Chuck to Bart and tells him to read it.
The story makes Bart stop and think, sitting down with Chuck and explaining that Chuck is not responsible for his mother’s death. Bart agrees that he's been a terrible father and it’s time he gets to know his son. Chuck takes Bart up on his offer to go see the hockey game after all.
At Blair’s party, Eleanor confronts Blair about her having lunch with Cyrus and tells her to stop meddling. Blair tells her mother that Cyrus cheated on his first wife. Hartbroken, Eleanor asks him to leave, which he does.
Then Cyndi Lauper shows up and tells Blair that Cyrus bought out her show so that she can come to Blair’s birthday party. Blair looks star-struck and Cyndi tells her that Cyrus is really in love with her mother.
She runs outside to catch Cyrus, and upon finding him, realizes he’s one-upped her and beat her at scheming. He knew what she was doing the whole time and he played along and won. Blair has a newfound respect for Cyrus.
Whether that respect continues after the next morning - when she sees them together and finds out he has, apparently, already moved in - or more schemes are on the way remains to be seen.
As for Serena and Aaron, she decides to give him another chance because she met Cyrus at the party and he happens to be Aaron’s father. Cyrus says that Aaron seems to really like her and that she’s special.
Serena decides to stop by Aaron’s studio and surprise him, but the plan backfires as Aaron and Danielle are having a romantic dinner.
When Serena tries to storm out and get upset, Aaron gives her a talk about how they never decided to have an exclusive relationship and that he likes to date a lot of people. Serena storms out.
But when Aaron shows up at Serena’s to pick her up for their date (which she had asked him on but then blew off), Serena decides to throw caution to the wind yet again and go with him anyway.
When Jenny shows up at Agnes apartment, Agnes greets her with a handful of her dresses. Agnes is livid at Jenny for going behind her back - which she learned when Scott Smith's office called the wrong number looking for the signed contracts and got her instead.
Agnes ends up burning all of Jenny’s dresses in a trash can fire and tells Jenny to get out of her apartment. Jenny goes back to Rufus to try to get him to sign the papers so that she can start working with Scott Smith.
Rufus refuses and Jenny leaves again. She tells Smith the news - that her parents will not sign the papers - and he tells her that the only way to proceed is emancipation. As in file suit and sever legal ties with them.
She says that she will do it. Gulp.
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