At the Starling City Museum, a security guard, Jerry stares at the Sherwood Ruby. His partner comes up and makes sure that he's okay, and Jerry says that Mrs. Hill wants them to move the gem to the vault because of the recent string of robberies. The two guards disable the security system and then Jerry knocks out his partner and takes the gem. The alarms go off and Jerry misdirects the security teams via the radio. He then meets with the man he's working for, Dodger, who is waiting in the shadows, and demands that the man take off the explosive collar he's wearing. Dodger does so and tasers Jerry unconscious.
At the lair, Oliver is sparring as Felicity works on the computers. Diggle tells Oliver to take it easy while Felicity brings up a file on the next person on the list, Ken Williams. When Oliver tries to leave, Felicity overrides the lock and seals him in. He comes back and Felicity tells him that ken is the widowed father of a ten-year-old boy. She refuses to help orphan people and suggests that he do some real good, but Oliver ignores her and reboots the system. Disgusted, Felicity says that she made a mistake by working with them and leaves.
Oliver tends to Slade, who is suffering from infection after Oliver took the bullet out of his arm. He plans to go back to the cave to get the herbs that Yao Fei had, but Slade warns him that he we won't last an hour.
At the manor, Frank Chen comes to see Moira and apologizes for being occupied with his interests in China. However, he's returned to Starling City since the Undertaking is close to completion. Moira tells her friend that she wants out now that The Hood is coming after her. She points out that Frank got into it because of what happened to his daughter Amanda and she and Robert joined to make the city a better place.
Oliver and Diggle go to Felicity's office and Diggle worries that she might decide to go to the police. Felicity comes in and Oliver admits that he was worked up on adrenaline and would like her to hear him out. He tells her that Ken returned the money that he stole and put his son to bed. As they talk, Felicity brings up a newscast on the Dodger, a thief who coerces people to steal for him by putting explosive collars on hostages. Oliver tells Felicity that he does go after people other than the ones on the list and asks her to help them take the Dodger down.
The next day, Dodger meets with his fence and gives him the Sherwood Ruby. When the fence, Cass Derenick, suggests he might not pay and his bodyguards pull guns on dodger, Dodger tasers all three of them unconscious, takes one of their guns, and then shoots Derenick dead.
Oliver, Diggle, and Felicity go to the diner and work out where Dodger will strike next. Carly comes over and says that she's dealing with a rowdy crowd, and Diggle offers to help them. Once she leaves, Felicity and Oliver point out that Carly is interested in Diggle, but he refuses to discuss it out. Diggle agrees to ask her out if Oliver will ask McKenna out, and then goes to talk to Carly. Felicity suggests that Oliver distract McKenna with some flirting and put a transmitter on her phone so they can listen in on her official calls. Meanwhile, Diggle hesitantly invites Carly out on a date and she says that she's been waiting for him to ask.
Laurel and Thea are getting lunch at a hot dog vendor from one of Laurel's former clients. As they talk, a purse-snatcher grabs Laurel's Thea's and runs off. The two women run after him and chase him into a dead-end alley, but he easily scales the gate and runs off. Laurel spots a wallet chain belonging to the thief that snagged on the gate and figures they can trace him.
Oliver stops by the station to see McKenna, who is surprised that he's coming anywhere near a police station. He thanks her for helping and compliments her on the fact that she got a promotion. McKenna admits that she's not having much luck and goes to put away some files, and Oliver slips Felicity's bug onto McKenna's cellphone. When she comes back, Oliver admits that he missed her and McKenna says that she hasn't been having much fun recently. He invites her out for dinner and she immediately agrees for that night.
Oliver returns to the cave and takes some of the herbs. An injured man, his hands tied behind his back, staggers into the cave and begs him for help.
Back at the lair, Oliver and the others listen in as Quentin calls McKenna and tells her that Derinick has turned up dead and his bodyguards were tasered unconscious just like Jerry at the museum. They figure that Dodger will be looking for a new fence and they set out to find him.
When Oliver comes home, he finds Thea checking on the chain from the thief's wallet, trying to identify the customer. Oliver has dressed for his dinner date and Thea points out that he seems nervous. He admits that McKenna knew him before the island, but is interrupted when Thea gets a call from one of the stores she's been calling. They have the purse-snatcher's name and address, and Thea calls Laurel to tell her that she's identified the thief, Roy Harper.
Diggle takes Carly to the park and they talk about her dead husband. She points out that Diggle bring up his brother on a romantic date wasn't a good idea, and tells Diggle to get out if it's too complicated for him to handle.
Oliver and McKenna go to a club and she asks him about his time on the island. She admits that she hasn't been on a date for a while and figures that Oliver must have changed. He admits that he had to make some tough choices and it changed him, but tells McKenna that he doesn't want to talk about it. Her cell phone rings and she tells the caller to put what the CI told them and put it in the warrant. Once she leaves, Oliver calls Felicity and has her check the bug.
The man says that his name is Alan Durand and he was on a fishing excursion when a fire swept over the boat. Alan says that he's the only one who made it and he got to shore, but then the soldiers found him and beat him. He then asks Oliver to untie him.
Dodger meets with his new fence, Claire Abbott, who has hired more bodyguards after she heard what Dodger did to Derenick. He figures that she has a better sense of judgment and asks if she can move the Sherwood Ruby. As they haggle over the price, McKenna and her men burst in. When Claire's men open fire, Dodger slips away in the confusion. McKenna tackles Claire while Dodger gets outside... and The Hood fires an arrow into the wall next to him. When Dodger refuses to surrender, The Hood closes in and Dodger throws an exploding collar at him, covering his escape.
Back at the lair, Felicity asks Oliver and Diggle about their dates. Neither man wants to talk about it and Oliver has her pull up the records on everything that Dodger has stolen. They all come from the Ominous Decade but nobody else sells the items. Oliver notices an advertisement for a charity and suggests that they set a trap after buying a suitable artifact.
Quentin brings Roy in and interrogates him while Laurel and Thea watch. Roy says that his father is dead and Quentin reviews his resume of minor crimes. The thief admits that he steals for his mother, who was addicted to Vertigo. She kicked the habit but her medical bills are adding up, and Roy says that he doesn't have the money that some people do. Thea, watching, says to let him go.
At the manor, Frank gives Moira an address and says that "they" will meet with her. Moira asks him if he can find a lead on where Malcolm is keeping Walter. Frank agrees but warns that they're both damned.
That night at the auction, an Ominous Decade brooch is in the place of honor. Oliver and Diggle patrol the crowd and confirm that the police are there as well. They're surprised when Felicity comes in wearing a fancy dress and tells them that she's put a transmitter on the brooch. Diggle spots McKenna but Oliver figures that he should stay away from her.
Felicity is monitoring the tracker and discovers that the brooch is on the move. She notices Dodge walking by with it and confronts him, and he turns and says that he'll just take it. Meanwhile, Oliver goes to check the bait when Felicity comes over... wearing one of Dodger's collars. She tells them to stay away but Oliver takes off while Diggle tries to disarm the collar. Felicity uses the tracker to give Oliver directions and he knocks out a biker and takes his motorcycle. He catches up to Dodger's car and finally takes out the tire with a flechette. The thief crawls out of the wreckage, takes out hiss detonator, and warns the helmeted Oliver not to do anything stupid. Oliver throws a flechette, severing his median nerve, and takes the remote from Dodger's paralyzed hand. Diggle removes the collar a second later and Dodger wonders why Oliver is after him when they both rob from the rich. He tries to hit Oliver with the taser but Oliver turns it back on him, says he's not Robin Hood, and walks away.
Oliver refuses to free Alan, figuring it's a trap. Alan insists that his guards were called away to deal with an altercation and Oliver finally tells him to turn around. As he starts to cut the ropes, Oliver hesitates and then says that he can't. When Alan wonders why, Oliver says that he doesn't know him and walks out of the cave.
The next day, Diggle meets with Carly and admits that he was thinking about how Andy would have been angry to see them together. However, Diggle figures that Andy would have been even angrier if Diggle did anything to hurt her. She tells him to go with his heart, not his head, and Diggle kisses her.
Thea goes to Roy's home in The Glades and knocks at the door. Roy figures that she's there so she can make herself feel good helping the poor, and knows all about her partying from the tabloids. She points out that she also had a dead father, a missing step-dad, and a damaged brother. Roy admits that she has some guts to come down to The Glades, and then gives her back her purse. As she leaves, Roy tells her not to believe every sob story a crook gives to the police and wishes her a good night.
McKenna is working at the station when Oliver comes in. She admits that she's ticked at him for shutting her out, and Oliver says that he lost the part of himself that enjoys life. He explains that he's not sure if he's worthy of being with anyone. McKenna kisses him and assures him that he is. As they prepare to leave for dinner, Quentin comes in and asks McKenna to help him with the vigilante investigation. She agrees and assures Quentin that they'll bring The Hood in.
Oliver goes back to the wrecked plane and gives Slade the herbs. He thanks Oliver for his help and asks if he got into any trouble, and Oliver says that nothing happened.
Moira meets with China White, who says that she'll be glad to help the friend of a friend. When China asks what she can do, Moira asks her to kill Malcolm.