Chai earned her B.A. in Journalism from the New York University and worked as reporter for the NY Sports Report on NY Ch. 1 News. She has performed in several stage plays in San Francisco and Los Angeles and appeared in independent and short films such as Waiting, Housewarming, 17 Years to Earth, and Til Death Do Us Part. She had supporting roles in Sugar: The Fall of the West (1998, with Michael McKean), Devotion, American Born, and Pacemaker.