Milano studied acting at The Lee Strasberg Institute and under Robert Carnegie and Jeff Goldblum at the Playhouse West. Beside several stage plays in the Los Angeles area, Milano portrayed Sophia in the 1996 short comedy Dick Richards, alongside Ashley Judd, Scott T. Trost, and Sean Whalen. She had guest roles in two Jack & Jill episodes (2001, with Stephen Macht, Clayton Rohner, and Michael Kagan) and in the Monk episode Mr. Monk Gets Drunk (2005, with Daniel Roebuck, Richard Libertini, and Peggy Miley). Also in 2005, she portrayed Maria Flores in the drama Transit and lent her skills to several independent productions.