Anyway, it's not like Oliver has much time to sulk. He's got a mob to infiltrate! Oliver goes to meet mafia man Frank Bertinelli, whose men have been targeted by the motorcycle shooter. He figures if he gets close enough to Bertinelli he'll be able to figure out who's behind killings. During their meeting, Bertinelli says he wants the contract to build the Queen Consolidated Applied Science Center. Though Moira wasn't in support of it, Oliver agrees to give it to him. Afterward, Bertinelli introduces Oliver to his daughter Helena (aka the motorcycle shooter!), and then sends them to dinner to discuss the contract.
Speaking of dinner, Tommy and Laurel head to an Indian restaurant on their date. Things seem to be going well until Tommy attempts to pay the bill, only to have his card rejected and then, to add insult to injury, confiscated. Ouch.
At the other dinner, Helena wastes no time asking Oliver about his time on the island. She wants to know if there was ever a day on the island when he actually felt happy about getting away from everything. He tells her there were many days where he didn't feel lost, but free. It's supposed to be a "deep" conversation, but it feels contrived especially because it doesn't really make sense for Helena, who is supposedly a tough character, to let her guard down so quickly with Oliver. Also, and maybe it's just me, but the two characters really seem to lack chemistry. They continue to talk until well after the restaurant has cleared out. Oliver compliments Helena's cross necklace and she reveals that it was a gift from her fiance. He's clearly disappointed (at least a lot more disappointed than when he found out Tommy and Laurel were going on a date), but then she tells him that her fiance is dead. (He's still got a shot!). Oliver tells her it's nice to be around someone he can actually be himself with, which again feels completely contrived. The dinner date is interrupted when Oliver gets an urgent call from Dig. Before he leaves, Helena warns him to be wary of her father.
Dig tells Oliver that Bertinelli's enforcer, Salvati, has been paying visits to people who owe the mob protection money. Oliver isn't interested in intervening but Dig says people are ending up in the hospital because of this enforcer. Dig warns him that the next target is the owner of Russo's, and Oliver tells him he just finished up a dinner there with Bertinelli's daughter. "Oliver, you're supposed to be going undercover -- not speed-dating," says Dig (he really gets the best lines).
Before Bertinelli's enforcer can hurt the Russo's owner, Arrow swoops in. He's not the only one that shows up though. Helena, who has her motorcycle helmet on, also intervenes. Eventually, Arrow and Helena spar with each other and before she can get away he takes her helmet off. He's shocked to discover that his new crush is the motorcycle assassin.
Back at the Queen mansion, Moira gets a visit from a mystery man -- the same one we've seen her plotting with in previous episodes. He wants to know if her convictions have changed following her brush with death. She tells him they haven't. He seems convinced and leaves. (I, however, am not so convinced). Moira gets a much more welcome visitor later on when Walter finally returns home and tells her that he missed her.
Elsewhere, Bertinilli meets with China White, who tells him that she and the Triad are not responsible for the attacks on his employees. Det. Lance and his colleague listen in on the conversation and determine that Starling City's latest assassin isn't an experienced shot.
At his hideaway, Oliver wonders why Helena would target her own family, which prompts Dig to ask him if he's falling for her. After all, since when does Oliver care about the motivations of his enemies? Oliver insists he's in control of the situation but Dig doesn't believe him.
NEXT: Oliver makes a move on Helena...