...Through Risk
S2 episode 2 Aired on October 23, 2015

Hoping for some downtime at Adriana’s house to figure things out, Grace instead finds herself getting swept up into preparations for Adriana’s next party. Spurred on by both Adriana’s encouragement and her need to prove to a competitive member of Adriana’s team that she’s not just a middle-aged housewife, Grace recruits a potential escort to attend the party. Adriana is pleased that Grace is exploring her “shadow side.” 

Meanwhile, Neil and Simon have suddenly found themselves almost working together. But when Simon arranges a date for Neil with Kate, who turns out to be a blogger hoping to write an exposé on the escort business, Neil figures out how to turn a potentially damaging situation into something that could take his own “business” to the next level. 

Emma, Simon’s father’s wife, returns to see Simon at his apartment. It’s evident that they’ve shared a very intimate history. She pleads with him to return the paintings to his father. Unable to resist, Simon reaches for her. Simon then sneaks into Adriana’s house to retrieve the paintings she stole from him. He shows up on his father’s doorstep with the canvases but throws them in the fire. His father surprises him by pulling him into a hug, relieved to have his son back at last, which is what he really wanted—because he has stage 4 cancer and little time left.