A native daughter whose family has lived there for three centuries, Hildy Good was once the most successful realtor in Wendover, MA, a quaint and now largely upper middle class coastal village, and one of the most successful small business owners on the North Shore, that was before among others Scott, her now out gay ex-husband, and their two young adult daughters, Tess and Emily, held an intervention that sent her to rehab for a drinking problem, something that Hildy does not admit that she had, especially in comparison to her long deceased mother. Coming out of rehab, Hildy drinks on the sly, she countering her now admitted drinking problem, which she doesn't see as much of a problem, a result of rehab, does not attend therapy or AA meetings, and is having financial problems in her real estate company being in a free fall in most business in town having been taken over by her former associate Wendy Heatherton, who stole her client list when Hildy was in rehab, although Hildy puts on a false front of not having any financial issues in she still largely offering financial support to Tess and Emily when they need it. In having sold her the house in which she and her young family live, Hildy develops a friendship with Rebecca McAllister, a lonely and needy woman new to town, that friendship for Hildy in Rebecca not only not judging her drinking, but partaking in it with her in their private time together. That neediness for Rebecca has resulted in her having an affair with married psychiatrist Peter Newbold, she once a patient of his. Peter has asked Hildy, who used to babysit him when he was a child, not to divulge that he has asked her possibly to sell his house if an out-of-town job comes through, Hildy taking from that that Peter's own marriage is in trouble. And despite her own troubles, Hildy offers her services to struggling Cassie and Patch Dwight to prepare their house for sale in they not having the funds to do so in all their attention, financial or otherwise, directed toward their autistic son, Jake Dwight. With the Dwights' house, Hildy asks another native son, Frank Getchell, owner of his own maintenance company, to assist despite Frankie being already stretched to the limit with work. In that process, Hildy contemplates starting something with Frankie, her high school crush, who may provide some stability that she needs in life.
