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Ben makes his first appearance in The Undergraduates, when Juliet goes to see him in prison. She informs him that the guys (Nate Archibald and Dan Humphrey) were easy to dupe but the girls (Serena van der Woodsen and Blair Waldorf) are presenting a challenge. However, she promises they will get it done. Soon after, he and Juliet fail to get Serena kicked out of Hamilton House and Columbia University. Meanwhile, Nate thinks Juliet is cheating on him and assumes Ben is her real boyfriend. She explains that Ben is her brother, and he is troubled. Meanwhile, she tries to frame Serena for trading sex for grades, and then tells Ben that Nate has distanced himself from Serena. However, her plan fails and Serena is, again, not kicked out of the school. Ben becomes agitated, and begins to become suspicious of Juliet's relationship with Nate (Goodbye, Columbia). Soon after, Nate's father Howard Archibald is attacked in prison, and he is imprisoned at the same facility Ben is. Later, Ben tells Juliet that he did so as a warning to her and in order to keep Nate safe, she breaks up with him (Easy J).
Soon after their break up, Juliet convinces her and Ben's cousin Colin Forrester to bring her as his plus one to Blair's birthday party. At the party, Nate asks Colin if he is Ben; and Colin realizes Juliet has been communicating with Ben in prison. When Juliet realizes Colin and Serena are having an affair, despite being teacher-student, she tells Ben. He orders her to get proof of them together and use it to get her expelled from Columbia. Juliet then places a camera in Colin's office to record them (War at the Roses). When Colin finds out, he cuts Juliet off both emotionally and financially forever, the same way he did Ben (Juliet Doesn't Live Here Anymore). As revenge, Juliet teams up with Vanessa Abrams and Jenny Humphrey to destroy Serena forever. At Chuck's Saints & Sinners party, they're able to ruin her relationships with Dan, Nate, and Blair. After the party, Juliet drugs Serena and leaves her alone in a motel room in Queens, and sends an email to Dean Reuther withdrawing her from Columbia (The Witches of Bushwick). In Gaslit, Serena is taken to the hospital for an overdose and Lily van der Woodsen has her involuntarily committed to the Ostroff Center. After she's away, Juliet informs Ben that she not only got Serena out of Columbia but got everyone to look at her differently. She tells him that she drugged her, and Ben is shocked; telling her that she went too far.
In The Townie, Serena enters counseling and begins to talk about Ben. She explains that she first met Ben at The Knightley School, where she ran away to boarding school, and he was her english teacher. He began tutoring her and they spent a lot of time together, growing close. One day, they ventured across state lines to a library and had car trouble on the way back during a storm. They stop at an inn and Ben goes to fix the car to bring Serena back to school. She tries to convince him to get a room with her, so they can consummate their feelings for one another, but he refuses her because he is her teacher. Meanwhile, Blair and Dan embark on a witch hunt for Juliet in Cornwall, Connecticut, where the school is located. They learn from Damien Dalgaard that after Serena left Knightley, Ben was fired for sleeping with a student. After learning this, they find the home of Ben and Juliet's mother and find out that they're siblings. When Juliet sees all three of them together, she heads to Manhattan to finally confront Serena. When she sees her, she explains that thanks to her signature on the affidavit; Ben is serving a five year sentence for statutory rape. Serena is confused, saying she never signed an affidavit; until she realizes Lily did for her. She confronts Lily at her holiday party, after promising Juliet to get Ben out of prison. Lily says that when Serena wanted to come home, no decent private school would accept her with her record. When she went to Knightly to speak with the administration, she overheard some girls gossiping about Ben and Serena. She told the administration that she had concerns with a teacher sleeping with her daughter; but then got involved with the state investigation. To cover her tracks. she signed the affidavit as Serena; effective committing fraud and getting Ben arrested. After her revelation, Serena leaves on a mission to get Ben out of prison.
When she returns, she and Chuck find the affidavit and try to blackmail Lily into getting Ben released. Lily tells her that the information about what she did can never get out, or else she will be arrested and the family will be ruined. Later, Serena goes to see Ben in prison but finds he was released. Outside, they meet up and go out for coffee (The Kids Are Not Alright). Soon after, they meet for breakfast and he tells her he's moving away to work for a friend. Disappointed, she asks Rufus Humphrey if Ben can move into the loft with Dan. Right after, Serena learns Ben wants nothing to do with her because Lily attempted to pay him off to leave town. When Rufus finds out, he agrees to let Ben move in to the loft. Meanwhile, Ben runs into Damien; who tells him that he knows he was the witness who saw him with Serena at the inn. Soon after, Ben physically threatens Damien; saying that he'll tell his father about him dealing drugs if he doesn't stay away from the VDW's (Damien Darko). Afterwards, he moves in with Dan, who is more than unhappy with the new arrangement. Dan teams up with Eric and Damien to get rid of Ben, and they set up a situation at a party to make it look as if Ben punched Damien. While Dan calls his PO to tell the story, Eric punches Damien. They confront Ben in front of Serena, and he is arrested for violating his parole. Right after, Damien tells Eric that he was only using him to get rid of Ben and they can't be friends anymore. The next day, Ben is released from jail when Dan tells the truth and they get on friendlier terms. He also enters into a relationship with Serena (Panic Roommate).
On Valentine's Day, Ben takes job with a catering company but lies to Serena that he's tutoring. Meanwhile, Blair brings Serena to the party to show that Ben was lying. After the party, they meet at a bar and he apologizes for lying about his job (It-Girl Happened One Night). On Eric's 18th birthday, he is blackmailed by Damien, who knows about the affidavit, into helping him complete a drug deal. When it fails, Damien demands a check for $100,000 to pay his clients back. When Lily finds out the whole story, she writes him a check herself and he leaves. Downstairs, he is confronted by Ben, who explains to him that he was the one who had Howard beat up and he could have Damien killed at any time. As a result, Damien gives back the check and Ben returns it to Lily. However, unbeknownst to them, Vanessa overheard the whole conversation (While You Weren't Sleeping). Soon after, Serena wonders why Ben hasn't been talking to her. She goes to see him at the loft and discovers his mother is visiting. The three of them meet up later and have a tour of the Waldorf penthouse, where Serena is living. When she excuses herself, she overhears Cynthia tell Ben that he has no chance of starting a new life when he's with Serena. Meanwhile, Lily knows Bass enemy Russell Thorpe knows about the affidavit and assumes Ben gave it to him. When Serena goes to look for it, she discovers it's missing and jumps to the same conclusion. At Chuck's party, Lily learns that Cynthia, not Ben, took it. Meanwhile, Ben and Serena break up, due to his not being able to get past what happened to him while with her. This is Ben's last appearance in the series.
- The Undergraduates
- Goodbye, Columbia
- Easy J
- War at the Roses
- The Townie
- The Kids Are Not Alright
- Damien Darko
- Panic Roommate
- It-Girl Happened One Night
- While You Weren't Sleeping
- Empire of the Son
- He likes to read Shakespeare.
- He is a fan of spicy food.
- His cousin Colin Forrester cut him off in every way after he was sentenced.