Blair and Serena are both trying to stay away from Valentine's day this year. Blair is really busy at the magazine...
The Thorpes decide to meet with the Basses to talk business decisions. Ben is looking for a job and Dan offers to help by getting him a catering waiter job.
"W" wants to follow an "It" girl on Valentine's Day and Blair suggest Raina. But in the back of her mind, she's just trying to watch what Chuck is up to. Serena decides to tell Raina that Blair still has feelings for Chuck and Raina decides to cancel her involvement in the "It" girl article.
Nate's father tells Chuck that Mr. Thorpe is planning to break Bass into small pieces. Chuck is in denial, believing that Mr. Thorpe couldn't have lied to him. Chuck also discovers that Lilly used to date Mr. Thorpe, so he uses it for an advantage, telling Mr. Thorpe that he will go on board if he tells them this conflict of interest.
Dan pitches an article to Blair for "W" after they see another movie. Blair finds out about Serena telling Raina and is unhappy. She also knows that Ben lied to Serena about tutoring and sends Serena to the party.
The party is full of people - Chuck spends time with Raina and Blair approaches Serena to make sure she notices that Ben is a waiter at the party but she doesn't seem to mind.
Lilly approaches Chuck and tells him that she has fought for him and threatens him for his actions. Mr. Thorpe announces that even though all of this has happened, he is still deciding to break up the company.
Dan and Blair are seen hiding and watching Chuck and Raina fight. She finds out that Chuck does actually have feelings for Raina and she holds Dan's hand, showing her sadness.
Blair decides to give Dan's article to "Vanity Fair".
Nate's father ends up getting fired from Thorpe but gives Chuck all of the passwords to the system. Eric is spotted meeting with Damian in a dark alley and threatens to tell the world that Lilly has lied about Ben.