America’s original playboy, Hugh Hefner, has filed for divorce after 11 years of estrangement from his wife and former Playmate Kimberly Conrad. TMZ reports that the Playboy magazine publisher claimed “irreconcilable differences” in his L.A. County court documents, listing the date of his separation from Conrad as January 21, 1998. Why the sudden need to make it official? Many have speculated whether Hef, who has gone through a slew of girlfriends in the intervening years, will ever marry again, but the answer could just as easily be financial: Since their 1989 marriage, Hef has supported Conrad, who still lives next door to the Playboy mansion with her two sons. Hefner is reportedly asking the judge to set spousal support at $20,000 months, justifying the relatively small amount with the fact that he’s already given Conrad some $12 million since their separation.