Caught unawares by a raging midlife crisis, Gary (Steven St. Croix) finds himself adrift in a sea of lust and jealousy when his stepdaughter (Candi Summers) brings her best friend Lola (Violet Blue) home for the holidays. His marriage to his wife Helen (Katie Morgan) already crippled by his blind jealousy, Gary falls head over heels for the pretty, Shakespeare-quoting drama student, but is he willing to give up his life, his wife, his reputation and his pride for a taste of the forbidden fruit? As his struggles sink him deeper into a morass of immorality and sin, he finds that the innocent Lola may not be the naif he thinks she is. Acclaimed director D. Cypher blends Shakespeare, dirty sex, comedy and a nod to great literature and uses the viewpoints of three different characters to guide our tour through one man's greatest fantasy and his worst nightmare.