Kate Madison's stylish second-hand clothing shop has been a big success in New York, supporting her and her four kids since her husband's untimely death. Now her children have grown up, they are ready to forge lives of their own. They all choose to play against the odds, much to their mother's dismay. Isabelle, a dedicated attorney, is in line to make partner at her Wall Street firm, when she falls for a client she represents in a criminal case. She tells herself she can make a life with him - but can she? Julie, a young designer, meets a man who seems too good to be true and falls under his spell. She marries him quickly, gives up her job, moves to LA to be at his side - is all what it seems? Justin is a struggling writer who pushes for children with his partner before they're financially or emotionally ready. Will the strain on the relationship take too high a toll? Willie, the youngest, a tech expert, makes a choice that shocks them all, with a woman fifteen years older. Kate - loving, supportive and outspoken - can't keep her children from playing against the odds. Can the odds be beaten?