Taking chances is part of life, but when you bet your future against the odds, it's a high risk game. 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 and 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, ignoring the danger signs. 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? No matter how much she loves him, in the end, the risks are their own and the hardest lesson as a mother is that she can't protect them from the choices they make.