Romi Rain was born into a family of Italian descent in Boston, Massachusetts. She began working as a nightclub dancer and stripper shortly after moving to Los Angeles at age 18. She also worked as a cocktail waitress in Las Vegas and dabbled in Glamour and Pinup modeling before getting picked up by the Playboy Morning Show. From that point on she became a regular at Playboy Mansion parties and started webcamming for Playboy Live. She then progressed to doing softcore porn on Playboy TV. After getting her multi-page spread in Hustler, she felt experienced enough to enter the hardcore porn industry.