Jessie Medina knows the job of School Development Director won't be easy, given that she is a woman working for a boy's school and that she is proposing new projects in a school operating on antiquated fundraising ideas. Jessie attempts to stage a concert to benefit the school, with or without the support of the alumni association's president, Roland Tobias. Though he seems intent on making her life difficult, she finds that the very man who challenges her at every turn can be her biggest ally. Balancing the new job and a personal relationship may hit a little too close to home and a little too close to the fears in her own heart.