Fleming was born on August 16, 1974, in Digby, Canada. She spent much of her early life in British Columbia, where her interest in performing began during her school years. Despite early family challenges, she remained focused on her creative path.

Before fully pursuing acting, she briefly worked as a model in Vancouver. However, her natural talent soon led her toward acting, where instructors and colleagues quickly recognized her quiet intensity and ease on screen.

Her early career included roles in Viper and a small part in Happy Gilmore. She later spoke fondly of that time, often reflecting on it with humor and humility.