At Cordelia's apartment, Wesley and Gunn play the board game Risk, until Cordelia tries to kick them out so she can sleep. They discuss plans to start their own company without Angel until Cordelia gets a vision about a large two-headed, fire-breathing demon. Angel bumps into a woman who runs a teen center. At the hotel, Angel reveals that he took her wallet and has dozens of pictures of the woman, including shots of her with Lindsey. Wesley and Gunn slowly approach the demon in the sewers and find themselves in over their heads with the 20-foot demon.
Angel confronts Merl in his apartment, demanding information about Anne, the woman running the shelter. She's connected to Wolfram & Hart but despite a couple of name changes in the past the woman herself is clean, so Angel visits the shelter and talks to her. Anne raves about Wolfram & Hart's help with the shelter and the plans for a charity fundraiser named the Highway Robbery Ball to gather money with the help of celebrities. A large demon named Boone confronts Merl for information on Angel and Merl is persuaded to provide that information.
Angel surprises Lilah in her car and expresses his happiness at being able to play the game now that he understands that there aren't any rules. Lilah tells Lindsey how worried she is about Angel, but their discussion is cut short as Boone arrives unannounced, wanting to deal with a grudge against Angel. Boone explains his past with Angel and the fact that they have a battle to finish. Wesley and Gunn rave about slaying the demon and despite their incredible fear, they're excited about their victory. The group leaves to look at a prospective location for their new business while arguing over its name.
Angel shows up at the shelter late at night, and Anne jokingly asks if he's stalking her. Angel offers all the evidence necessary to confirm that he is, and then tries to warn her that Wolfram and Hart are going to steal money from the fundraiser. Lindsey arrives and pretends to be protecting Anne, bringing Boone with him to fight with Angel. Lindsey tries to defend the law firm to Anne but the information Angel's provided her worries Lindsey, and he discusses the dangerous possibilities with Lilah.
Wounded from the fight, Angel returns to the shelter and Anne expresses that she is willing to ignore just about anything if it means aid to the shelter. Angel gives her a tape to play at the fundraiser, but Anne refuses to risk the shelter. At the Ball, a video of Holland entertains those at the fundraiser. Lilah introduces Anne to one of her bosses, Mr. Nathan Reed, while Lindsey reviews the security plans for the ball.
While actors collect money and jewelry from the rich attendees, Angel reveals his presence, which leads to a fight between the vampire and Boone on the balcony, and they eventually fall to the main floor. Lindsey searches for the incriminating tape, but it's revealed that Angel is not in possession of the tape and Boone is actually working with him. Anne plays the tape before Lindsey and Lilah can stop her, but it contains only clips of Cordelia and Wesley acting goofy for the camera, so its apparent that Angel never had anything to incriminate the lawyers in the first place. To add even more embarrassment to the situation for Wolfram & Hart, Boone has taken off with the donations.
Lindsey confronts Mr. Reed about not being able to kill Angel, and it is revealed that Angel is an important figure in the upcoming apocalypse, but because his role is unclear, he must stay alive. Boone confronts Angel at the hotel, offering up the 2.5 million dollars in charity donations as the stakes for a fight between the two of them. Again wounded from battle with Boone, Angel presents the money and jewelry to Anne for the shelter, who is undisturbed by the real and metaphorical blood on the money.