After living in Los Angeles for 10 years, O’Donnell returned to New York, where she feels more at home with the matter-of-fact attitude toward celebrity. In late 1999, she adopted a third child, Blake Christopher. O’Donnell received two Emmy awards in 1998 for “Outstanding Talk Show” and “Outstanding Talk Show Host” (the latter for which she illustriously tied with established talk show great, Oprah Winfrey).

In November 2000, O'Donnell admitted that she is planning to leave her talk show after her contract expires in 2002 in order to spend more time on her nonprofit organization, Rosie Adoptions. The organization helps facilitate the process of adoption between birth mothers and adoptive families. In early 2002, Rosie began making headlines again, with word that she would officially come out as a lesbian in her autobiography Find Me (April 2002).