While Diggle screws up a romantic walk with Carly by bringing up his brother (a.k.a. her hubby), Arrow has an equally disastrous dinner with McKenna, who can't seem to stop asking him questions about the island. Not exactly first-date convo. Her questions trigger some bad memories and Oliver tells her he had to make some tough choices. When McKenna pushes the topic, Oliver tells her he doesn't want to talk about it (and rightfully so!). Luckily for him, the conversation gets cut short when McKenna gets a call about The Dodger. After she leaves, Oliver calls Felicity and asks her to activate the bug on McKenna's phone.
Cue flashback: Oliver questions the man in the cave about his identity. The man tells him he was on a fishing expedition with his class when a mechanical failure on their boat prompted him to jump ship. Oliver continues to press him. He wants to know what happened to the rest of the class, and the man says he thinks he was the only one to make it out alive. He tells Oliver the guards on the island beat him, bound him, and left him to die. Though it looks like Oliver is about to help, he can't bring himself to trust the man enough to untie him. Instead, he leaves him there and goes off to give Slade the herbs. Later, Slade -- who is feeling much better -- asks Oliver if everything went okay during his expedition. Oliver tells him it was fine, but he's clearly haunted by his decision to leave the helpless man.
In Starling City, The Dodger meets with another buyer. They're about to complete the trade when McKenna and a slew of other cops arrive on the scene. The Dodger manages to get away unscathed, but Arrow catches him outside. He doesn't have the upper hand for long, though. The Dodger throws a bomb in Arrow's direction and slips away once again.
Back at the hideaway, Felicity asks the boys how their dates went, but they're not exactly in the sharing mood. (Side note: Any New Girl fans out there? For some reason Felicity's relationship with the guys reminds me off Jess' relationship with her roommates in season 1). They look into The Dodger's records and realize he has an affinity for Spanish antiquities. Oliver suggests they lure The Dodger to an upcoming cancer benefit with a jewel donated by the Queen family because yes, they are just that rich.
Meanwhile, Frank sets Moira up with someone who can presumably help her get out of the undertaking. But Moira's not done yet. She asks Frank for one more favor. She needs his help finding a lead on Walter. Apparently Malcolm is the only one who knows his whereabouts, and Moira tells Frank that if their "plan'' works, she can't let it ruin Walter's life. Later, Moira meets with China White and asks her to kill Malcolm. Ah, so that's her plan. Let's see how well this works out.
At the gala, Felicity shows up -- without her glasses! -- in a dazzling gold dress. I imagine this was supposed to be her Pretty Woman moment, but to my disappointment both Oliver and Diggle look only mildly impressed. Their reactions are the least of her worries, though. Felicity tracks The Dodger and discovers he's picked up the Queen family broach. Wait, I thought he was called The Dodger because he never committed his own crimes? Anyway, she tells The Dodger he needs to bid on the broach if he wants it. He's not exactly intimidated.
NEXT: Felicity sports a new accessory...