On 2nd of July 1968, David got married to Michelle Cook. They were in romantic love affairs since they were in their college days. As a married couple, they remained together for about a decade and finally dissolved their married life in 1978.
A few months later, David was seen with Merrill Markoe. Merrill Markoe is an author and writer. They dated each other as a boyfriend and girlfriend for about ten years and they finally broke up in 1988.
It seems like his love life with Merrill Markoe came to an end in 1988 as she found him being infidel towards her. In 1986, he met Regina Lasko and since then be began dating her secretly. Regina Lasko is a Production Manager and she is famous for her work in Another World, Saturday Night Live and many more. They dated each other for more than two decades and they finally got married on 19th of March 2009. At the end of 2003, they also welcomed their only child a son, Harry Joseph Letterman.
David was enrolled at Broad Ripple High School. He graduated from there but with the lower grades and that's why he joined Ball State University. He finally graduated from there in 1969 with a major in Radio and Television. He then joined WNTS and began serving them as a radio talk show host. Later he joined Indianapolis television station WLWI and he worked there as an anchor, and weatherman. From June 1980, he began running his own comedy show, The David Letterman Show.
In 2002, David Letterman sold his New Cannan, Connecticut home for $1.1 million. The 3,925 square feet and three bedrooms house which sits on 2.4 acres was listed in the market in 2001 for a listing price of $1.3 million and was bought by Letterman in January 1983 for $400 thousand.
Letterman bought a 108 acres estate in Westchester, North Salem, in two phases- first 88 acres in 1994 for $5 million and the rest in 2007 for another $5 million.
For hosting the show, Late Show with David Letterman, he earned the salary of $32 million per year. Though his annual income has dipped to $20 million he still has an estimated net worth of $425 million. Letterman makes his fortune with his production company Worldwide Pants Incorporated and from real estate investments.