Desmond Green is an aspiring college student with aspirations to become a lawyer. However, Desmond has a criminal record that causes his college admissions to be rejected and prevents him from finding a good-paying job. Desmond takes the necessary classes he needs while paying for them as a male escort. Darlene is a divorced lawyer in her late 40's who is an e-magazine publisher and criminal justice professor who seeks pleasure through a dating app. Regardless of achieving success, her last marriage has left her suffering low self-esteem and loneliness. To regain her confidence, she seeks Desmond's services, hoping to find the confident woman she was thirty years ago. However, Darlene and Desmond get more than they bargained for. Both become involved in emotional and physical entanglement, as they both must overcome their age-gap taboo, classism, and bigotry.