Diller's sexual orientation has been discussed in the media. In James B. Stewart's 2005 book DisneyWar, former Disney head Michael Eisner refers to Diller as "a homosexual." In 2001, "New York Magazine"'s Maer Roshan wrote:The recent wedding of Barry Diller and Diane Von Fürstenberg epitomizes the media’s convoluted approach to covering gay celebrities. I would not presume to speculate on their relationship, which is said to be a warm and genuine one. But it’s also true that Diller did not live as a monk before his marriage at the age of 59 – in fact, while Diller is often referred to as bisexual, he has lived most of his adult life as a more or less openly gay man. He has had both short-term boyfriends and long-term relationships (including one with a former editor-in-chief of "The Advocate"); he appears frequently at gay parties and gay benefits. His sexual orientation has even been referred to in print with regularity.