Christy ventures back into the dating world for the first time since she has been sober. Bonnie babysits Roscoe and decides to teach him blackjack.
Christy is a waitress at a posh Napa Valley establishment who is four months sober and doing her best to be a good mom and overcome a history of questionable choices. Her sobriety is tested when Bonnie, her recovering alcoholic mom, reappears chock-full of passive-aggressive insights into Christy's many mistakes.
Bonnie joins Christy's already complicated circle of relationships: her handsome, married boss - and lover - Gabriel; the restaurant's hot-tempered chef, Rudy; her pretty, 16-going-on-25-year-old daughter, Violet; her sweet but overly honest son, Roscoe; her irresponsible ex-husband and Roscoe's father, Baxter; and Violet's clueless boyfriend, Luke. Christy tries to remain positive as she pursues her new path in life, but she faces an uphill battle, surrounded by a dubious support system - and a copious amount of dysfunction.