Angelica Ross was born on November 28, 1980 in Kenosha, Wisconsin, then raised to the north in nearby Racine. Ross, a trans woman, has said she was perceived as feminine from a young age. In 1998, when she was seventeen, she came out as gay to her mother, an evangelical Christian. Her mother did not receive the news well as, according to Ross, "she told me I should commit suicide or she would, because she couldn't have someone like me as her child." Ross considered ending her own life and overdosed on medication but survived.Upon graduating high school at 17, Ross briefly attended the University of Wisconsin–Parkside before dropping out after one semester. Ross decided to join the U.S. Navy (after her parents signed a waiver so that she could join as a minor) in order to qualify for the G.I. Bill. Ross initially moved to Rochester, New York, before being stationed in Yokosuka, Kanagawa. After six months of service, she requested and received an "uncharacterized" discharge under the "Don't Ask Don't Tell" policy (which was then in force) due to being harassed by enlisted men who coerced her into saying she was gay.Ross moved back home, and made friends with a drag queen named Traci Ross who helped her begin her gender transition at the age of 19. Upon discovering that she was transitioning, her mother threw her out and Ross moved in with her biological father (who was slightly more accepting of her) in Roanoke, Virginia. Although Ross and her parents were estranged for a time, she states that their relationship has since been mended. During the six years that she lived in Roanoke, Ross worked as a waitress at Applebee's so that she could earn enough money to pay rent and attend cosmetology school. She was let go from her waitress job due to discrimination. Ross then moved to Hollywood, Florida and worked as a model and escort, then web manager, until 2003. She started a web development and graphic design business and took acting classes. She later moved to Chicago to become the employment coordinator for the Trans Life Center.