Ned Rochlin, an organic farming hippie, loves unconditionally. His overly trusting nature often makes him come across to the world as an idiot. It is one of those trusting but idiotic acts which lands Ned in jail. After he is released on parole, Ned loses everything: his organic farming girlfriend Janet, a place to live as Janet claims the farm as her own, and perhaps most importantly his dog Willie Nelson as Janet also claims him as hers despite she only doing so to spite Ned. Not wanting to burden his oft neglected mother Ilene, Ned becomes the responsibility of his three sisters, Liz, Miranda, and Natalie. A family pact prevents them from doing the easiest thing, which is to give Ned money to live where he wants. Instead, Ned is shuttled between the sisters, whose own lives are affected by Ned's overly trusting acts. Liz and her documentary filmmaker husband Dylan Anderson's politically correct parenting of their adolescent son River is stifling his happiness. In addition, Liz is unaware that more than Dylan's eyes are wandering. Miranda, a writer for Vanity Fair, has the biggest assignment of her career and will do whatever needed to get the story she wants. In that singular focus, she and her neighbor Jeremy don't have the clarity to tell each other that they truly do like each other. Bisexual Nat, in a long term relationship with a lawyer named Cindy, lives in a communal situation in an effort not to make that final commitment to Cindy, who literally and figuratively wears the pants in their relationship. In Ned's acts, he may expose the issues that each of the sisters faces and that they were unwilling to address on their own.