At Cordelia's apartment, Wesley and Gunn play 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-flatulating demon. Angel bumps into a woman who runs a teen center. At the hotel, it is revealed that Angel took her wallet and has a dozens of pictures of her, 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, so Angel visits the shelter and talks to her. Anne raves about Wolfram & Hart's help with the shelter, and their plans for a charity fundraiser called the Highway Robbery Ball, designed to gain donations 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 help Wolfram & Hart in order 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.
Lilah and one of her thugs accost Merl for information while Angel shows up at the shelter late at night, and uses the pretext of bringing her some clothing donationsthe clothes are some that Cordelia has left at the Hyperion. 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 & Hart are going to steal the money from the fundraiser, leaving only scraps for her. 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 tells Angel that she's worked out he's a vampire but that doesn't faze her (even stating she thought vampires were cool until she met one). She states that she's seen terrible things happening to kids on the streets of LA and is willing to ignore just about anything if it means aid to the shelter. Angel points out that out of all the money that will be raised at the charity ball she'll likely only see around 5% of it, but Anne tells him even that would be enough to keep the shelter running for a couple of years. Angel urges her to think about where the other 95% is going, telling her that the money she'll make from the party will have blood on it even if she can't see it. He asks her to get him inside the fundraiser, telling her he has a video tape with footage that will expose Wolfram & Hart, assuring her its the right thing to do. Anne reminds him that all she cares about is helping the kids at the shelter, and refuses..
At the Ball, a video of Holland talking about the shelter entertains those at the fundraiser. Lilah introduces Anne to one of her superiors, Nathan Reed, while Lindsey reviews the security plans for the ball. While actors pretending to be bandits 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. With Lindsey and Lilah on the other side of the room it's Anne, who had actually been persuaded to help, who is the one to get the tape to the player. Lindsey and Lilah scramble across the floor to stop her, an act which is captured on film, but fail and the tape plays... but it contains only clips of Cordelia and Wesley acting goofy for the camera. It quickly becomes clear that Angel never had anything to incriminate the lawyers in the first placehe was just trying to embarrass them, a plan that has worked thanks to their frenzied attempt to stop him. To add even more embarrassment to the situation for Wolfram & Hart, Boone has taken off with the donations. Anne confronts Angel accuses him of having no intention of exposing Wolfram & Hart's scheme, and he confirms this saying they would have only covered it up so he's willing to settle for making the firm look bad. Anne reminds him that she's lost all the charity money but Angel tells her that he doesn't care, reminding her that the money was tainted, and leaves.
Lindsey and Lilah are hauled in front of Nathan for losing the money, embarrassing the firm and hiring an assassin to kill Angel who was actually in league with him. He warns them to start accumulating victories fast, when Lindsey demands to know why they can't be allowed to just kill Angel since he's so much trouble for them. Nathan informs him that according to the various prophecies Angel will play a key role in the upcoming apocalypse. What isn't known, however, is whose side he will be fighting on. Wolfram & Hart are keen for Angel to have turned evil by that point, and his obsession with Lindsey and Lilah is hoped to help contribute to that. Nathan finishes by warning the two that Angel is invaluable while they are replaceable.
An Angel dumps his files on Anne, he finds Boone waiting for him in the hotel's lobby and isn't surprised he came back. Boone throws the bag containing the charity donations, which amounts to two-and-a-half million dollars, down in front of him willing to lay it on the line for a fight between the two of them. Angel tells Boone he's gambling a lot, and Boone responds that he has to know who would win. The two then launch themselves at each other.
Later, a battered but victorious Angel presents the money and jewelry to Anne for the shelter telling her she'll need to hide it from Wolfram & Hart. Anne, undisturbed by the real and symbolic blood on the money, accepts it.
- Accidental Public Confession: Subverted; Lindsey and Lilah think Angel has tape-recorded them discussing their Evil Plan to steal the charity money. Angel points out that it's very difficult to bug someone as Properly Paranoid as them. The tape was only meant to be a distraction so Boone could steal the money himself.
- Actor Allusion: On video, Wes does an impression of Sean Connery. In Real Life, Alexis Denisof starred with Connery in First Knight.
- An Axe to Grind: Wes & Gunn hunting the two-headed fire-breathing thing.
- Armour-Piercing Slap: Anne slaps Angel when she finds he used her as a distraction to steal the money himself.
- Bad "Bad Acting": Cordelia is shown on tape rehearsing for an audition by using a coat rack. One of the celebrity actors quips that he finds the coat rack more convincing.
- Bald of Evil / Four Eyes, Zero Soul: Nathan Reed, Lindsey and Lilah's new boss.
- Battle Discretion Shot: Gunn & Wes fighting the two-headed tunnel creature. Angel's final battle with Boone.
- Chekhov's Gunman: Anne Steele was last seen in the BTVS episode "Anne", where she called herself Lily and was a runaway herself.
- Continuity Nod
- Anne mentions how she used to be a Vampire Vannabe until she met an actual vampire, referring to the events of BTVS "Lie to Me".
- One of the fundraising celebrities recognizes Wesley as "the guy who's dating Virginia Bryce." Likewise the 'Wyndam-Price Agency' argument — both callbacks to "Guise Will Be Guise".
- "We'll catch you when you fall!" is from Cordelia's proposed advertisement for Angel Investigations in Season One.
- Crash-Into Hello: Angel uses this to lift Anne's wallet as well as get an introduction.
- Creator In-Joke: "This thing where your character's gay...is that just for ratings?" How many times do you think Alyson Hannigan was asked this? Also Wesley doing a James Bond impersonation — his character was first described as "Thinks he's Sean Connery when he's actually George Lazenby."
- Danger Takes a Backseat / Nothing Good Ever Happens In A Parking Garage: Angel does this to put the frighteners on Lilah Morgan; it's not as if she can see him in the rear mirror.
- Door Judo: Poor Merle.
- Egocentric Team Naming: Wesley, Cordelia and Gunn all want their new agency to be named after themselves.
- Evil Is Petty: Wolfram & Hart's plan is, basically, to overcharge a charity event so those in need get scraps instead of the full amount. Even Faith at her worst would see this and go, "Oh come on!"
- Fartillery: Wes and Gunn are about to take on the creature Cordelia saw in her vision.Wesley: "No, no, wait. Wait. Wait until its back is turned...Now!"
[They jump out into the main tunnel only to flinch back from a jet of flame]
Gunn: "I thought she said he breathed fire!"
- Felony Misdemeanor / Cut Lex Luthor a Check: Compared to Wolfram & Hart's usual actions and the vast resources at their disposal, embezzling a few million dollars from a charity ball is definitely more "naughty" than "evil".
- Grey-and-Gray Morality: The Senior Partners are deliberately setting out to blur Angel's moral boundaries.Nathan: "Which side he's on is the gray area, and we're gonna continue making it as gray as possible."
- Have We Met?: Averted; Angel (posing as a human) and Anne (then calling herself "Chantarelle") had a brief encounter in "Lie to Me", but neither of them appear to remember each other.
- Honor Before Reason: In their first fight back in the 1920's, Boone let Angel leave because the sun was coming up, and he wanted to defeat him personally rather than watch him get dusted. When Lilah and Lindsey ask why, he even says "Don't you know anything about honor?" In the present day Boone has a chance to walk away with over two million dollars, but he returns to challenge Angel to single combat, winner takes all simply because he has to know who's better.
Anne: (referring to the sticky red substance all over the money) What's this?Angel: Blood.Anne: It'll wash.
- Inverted by Anne.
- Humans Are the Real Monsters / The Triple: Angel is surprised that Anne isn't afraid of him, given that she's met vampires before.Anne: "Well, I've seen worse things since. A fourteen-year-old girl sitting in her own blood after a rough trick and dozens of people just walking right by, so no, vampires, demons, even lawyers pretty much don't impress me."
- Hypocritical Humor:
- Wesley is talking about the new agency they'll create. "We'll catch you when you fall!" Vision Girl promptly keels over in the background without anyone noticing.
- Lindsay protests to Lilah that it can't be his fault if Angel has proof because he he never talked about stealing the money in public... and he says that in public, something Lilah is quick to point out.
- The Informant: Merle spends a lot of the episode getting information for Angel or selling out information about Angel whenever threatened.
- In the Hood / Dressing as the Enemy: Angel takes the place of the vampire-detecting demon.
- Ironic Echo: Angel says there's "blood on that money" that Wolfram & Hart are raising for the shelter. When Angel gives the money to Anne, it's literally true as he had to fight and presumably kill Boone to get it.
- Is This Thing Still On?: The fake tape shows Wes and Cordy arguing and goofing off in front of the camera.
- Meaningful Name: 'Anne' is Buffy Summers middle name; Lily asked if she could use that name at the end of "Anne". 'Steele' shows how her character has changed from that Cloud Cuckoolander runaway who would attach herself to any strong protector, to the motivated and self-confident helper of runaways she is now.
- Multiple Head Case / Playing with Fire: The unseen creature in Cordelia's vision.
- Must Be Invited: Angel doesn't need an invite to walk into Merle's place because he's a demon. He does make sure to get an invite to the charity fundraiser from Anne so he can sneak into the joint. note
- Noble Demon: Boone, a Blood Knight of a demon with a sense of honor.
- Noodle Incident: That "disagreement over a senorita" in Juarez in the 1920's that caused Boone to challenge Angel in the first place.
- Not So Dire: Wesley and Gunn staring each other down and talking about "facing the odds." Turns out they're playing Risk.
- Oh, Crap!: Gunn and Wes sneak a quick peak at whatever's roaring away in the tunnel ahead. They duck back with terrified expressions.Gunn: "The tunnel is almost twenty feet tall. It was crouching!"
- Perp Sweating / Rule of Three: Poor Merle again.
- Photo Op with the Dog: The charity event. Holland also had one done in the charity's promotional video.
- Posthumous Character / We Care: The late-unlamented Holland Manners appears in a video promoting Anne's shelter for runaways, apparently produced by Wolfram & Hart.
- Power Fist: Boone has steel cords that magically wrap around his fists to make knuckle dusters.
- Power Trio: After disposing of the double-headed fire-farter, Cordelia, Wesley and Gunn realise they do in fact make an effective demon-fighting team without Angel. If only they can agree on a name.
- The Reveal: The Senior Partners want Angel alive because "the vampire with a soul" is meant to play a key role in the Apocalypse. They just don't know which side he'll be on.
- Running Gag: The stylised angel on the Angel Investigations card being mistaken for a lobster.
- She Is Not My Girlfriend: Angel donates Cordelia's clothes, saying they were left at his place by someone who won't be returning. Anne naturally assumes he means an ex-girlfriend — Angel immediately blurts out, "God no!"
- Shout-Out: When Angel examines her driver's license, Anne's address is listed as "Willoughby Ave." Anne Steele and John Willoughby are characters in Sense and Sensibility.
- Sinister Surveillance: After Angel's apparently innocuous meeting with Anne, we discover he has extensive photographs of her in his apartment.
- Stealth Hi/Bye: Angel somehow vanishes from the backseat of Lilah's car without opening the door.
- Two Lines, No Waiting: The Angel plot and the Wes/Gunn/Cordy plot — a trend that continues until "Epiphany".
- Villain Ball / Stupid Evil: So a vast and powerful law firm that likely makes billions has to organize and steal from a charity fundraiser? For the Evulz or what? They're not even using the youth center as a front for interdimensional slave labor or anything.
- It's for PR.
- Villain with Good Publicity: Yet another attempt by Wolfram & Hart to do this.
- Villainous Demotivator: When Lindsey complains about how they're not allowed to kill Angel, Nathan says the aim is to bring Angel over to the Dark Side and if Angel killing Lindsey and Lilah achieves that, that's just too bad. "You're expendable. Angel isn't."
- What the Hell, Hero?: Angel says the Wolfram & Hart intend to steal the 95% of the money raised but then he lets Boone steal all of it. Fortunately Boone has his own sense of honor.
- World's Smallest Violin: Lilah says that if Boone kills Angel the Senior Partners will be pissed.Lindsey: "Boo-hoo. Let me wipe away the tears with my plastic hand!"
- You Have Failed Me: Nathan tells Lilah and Lindsey that he's not as fond of them as Holland was, and if they want to save themselves they need to start "piling up wins, fast".