another affair with a gay congressman's wife. Natalie Zea as Karen Darling; The eldest daughter in the Darling family, with four failed marriages under her belt. She possesses an MBA from Columbia University, as well as running the family's charitable foundation. Nick and Karen were romantically involved at one point in time when they were younger (she lost her virginity to him). Nick proposed to Karen in Italy when they were both 19. They never ended up getting married, making Karen resent the fact that it didn't turn out that way. She later begins a relationship with Simon Elder so she can spy for her father, but ends up forming slight feelings for him, alienating her from the rest of her family. Her relationship with Simon ends when he trades her for a business deal with Tripp on their wedding day. She later finds out that she is pregnant with Simon's baby, but loses it in a miscarriage when she falls down the stairs at the Darling house. Karen starts a relationship with Nick in Season 2. Glenn Fitzgerald as Brian Darling Sr.; The middle child of the Darling family. In his 30s, he is an Episcopal priest, even though he has an illegitimate child who he won't admit is his. He loathed Nick George as a child, which continued when Nick first started working with the family. He and his first wife, Mei Ling, divorce when she finds out he has an illegitimate child, Brian Jr., and marries Andrea later, a cancer survivor. Andrea throws Brian out when she finds out that he went to DC for a tryst with his ex-wife and he turns to Nick for help. The two bond and the animosity is lessened between them. He resigns from Darling Enterprises after a position of vice-chairman which he believed was supposed to be given to him went to Nick, also with the partnership between Tripp and Simon Elder. He rejoins the church after Andrea becomes healthy again. Seth Gabel as Jeremy Darling; Juliet's twin brother and the youngest member of the Darling family. Addicted to cocaine, he is frequently seen hung over, chain-smoking and pleading with Nick George to get him out of a jam. Completely oblivious to other people's suffering and unable to imagine a life worse than his, Jeremy often fears that he is the family disappointment and that his father abhors him. Jeremy