Waldman was born in Newton, Massachusetts, and she graduated from Simmons College with a degree in Economics. Prior to her broadcasting career, Waldman worked for many years as an actress and singer in musical theatre. Her most notable role was as Dulcinea in "Man of La Mancha." Her rendition of "There Used To Be a Ballpark" appeared on historian David Pietrusza's 1995 WMHT-TV documentary "Local Heroes: Baseball on Capital Region Diamonds." Also, she has performed the National Anthem at many Yankee home games (most recently before the 2020 Yankees home opener on July 31) as well as the 1986 ALCS Championship game 7 at Fenway Park.