David Letterman & Regina Lasko – Together For 34 Years

Even though they started dating in 1986, they only decided to get married by 2009. David Letterman and Regina Lasko even had a six-year-old son by that time, born in 2003. We’re not surprised about David’s hesitance to get married again; after all, he had already gotten divorced once when he met Regina.

No matter his past, they seem to be the perfect match. Throughout their relationship, David’s been able to make a $400-million fortune. He found most of his success through hosting Late Night with David Letterman, which ended in 2015. He has since started a new show called My Next Guest Needs No Introduction.