How do you paint a regret? As single parents each with two young daughters, Tearza and Ryan struggle with loss, love, and their mistakes. Tearza is devastated with guilt over her husband's sudden suicide and the loss of her job. She's worried about the grief consuming her daughters, Marci, and Ella, and afraid to move forward because every time she loves something she loses it. Ryan lost his wife through divorce due to Post-Partum Depression which led to her chemical dependency. Obsessed with his desire to make partner in a prestigious law firm, he struggles to balance work and his two daughters, the same age as Tearza's. Wounded by his past mistakes and broken promises as a husband, he fears he's failing as a father and mother to Sarah and Gracie. Time is running out. If he doesn't make changes soon, he'll regret it for the rest of his life. Together, Tearza and Ryan learn to make difficult choices that come with risk. Their relationship follows the circle of life through four seasons in one year. Along the journey, they discover how their worst regrets become their greatest blessings.