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In 1961, at the age of 20, he wed a woman named Margaret Hayes. Chuck Woolery's second wife was actress Jo Ann Pflug, with whom he shares a daughter, Melissa.The couple raised three children: adopted son Cary, who is now about 56 or 57 years old; daughter Katherine (known as Kitty), who is now about 48 or 49 years old, and another son, Chad,, who is deceased. Pflug, who is now 74 years old, is best known for her role as Samantha "Big Jack" Jack in the hit 1980s TV series The Fall Guy, starring Lee Majors. They announced their plans to divorce in early 1982.

No compromise could be reached and Griffin decided to fire Woolery.

Woolery also hosted such game shows as The Big Spin (1985), Scrabble (1984-1990), The Dating Game (1997-1999), Greed (1999-2000) and Lingo (2002-2007).

In 1991, he had his own daytime talk show, The Chuck Woolery Show, which only lasted a few months.

The family also included Chuck's older sister, Sue, who is described as a nursing assistant in an October 28, 1991 People magazine article by Tim Allis.

Chuck Woolery aspired to a career in the music industry, but enlisted in the United States Navy instead.

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