"The Curious Complications of Role Playing" is a film about Nancy, a woman in her mid 20s who just happens to be a dominatrix at an S&M dungeon. For the first time in her life, Nancy is falling in love with Colin, a sweet teacher in his mid 20s, who doesn't have any idea what Nancy's profession is. At the end of their date, Nancy and Colin have sex for the first time. Although it's not exactly bad, Nancy finds it way too "sweet" and "polite". Panicked, Nancy ditches Colin in the morning to go to work. After having a particularly awkward S&M session with spaghetti, Nancy realizes she's much rather be spending time with Colin than her clients. Nancy meets Colin outside his school and insists he come over to her place. Nancy welcomes Colin, sprawled out on her bed in a negligee and tells him she wants to act out one of his sexual fantasies. Nancy then plays out a school girl fantasy Colin has, and although she attempts to be submissive, her inner dominatrix comes out when Colin has a hard time taking charge. After she hurts and humiliates Colin, he questions her behavior and she throws him out. Nancy knows she has to reveal to Colin her true colors, and does so when she shows up at Colin's home in her leather skirt and bustier. In the end it's through S&M that Nancy tests both her and Colin's boundaries to discover whether they can find a common ground.