Charismatic multi-millionaire Ray Jones, a pivotal figure in the lives of Whitney, Laura, Damian and Caseman, returns to town and turns their worlds upside-down -- starting with a nude proposal. Meanwhile Carlos interviews for a high-end law firm, and a traumatic event has Damian considering new job options.

Ray hires Laura and Caseman to decorate his new office space, and while working together, they figure out that they have chemistry. However, Ray learns that Caseman means more to Whitney than he originally thought. Meanwhile Damian goes to work for Ray and uses his boss' name to pull a favor for Carlos, who lands a new job, and Mae finds out about a woman who may be her mother while babysitting for Laura and Caseman.