By Gretchen Edgren

The British magazine FHM once estimated that Hugh M. Hefner had made love to 3000 women in his lifetime.

An exaggeration, Hef says (but fails to supply corrected statistics). The important thing, he pointed out to Bill Zehme, his Playboy Interviewer in the January 2000 issue, is quality, not quantity. In fact, the first thing Mr. Playboy will tell you about himself is that he's a romantic -- and that, as such, he's into relationships, not mere statistics. Which may explain why nearly all of his Special Ladies, as he affectionately calls them, remain Hef's friends to this day.

No matter how many, or how few, women he's known and loved, there has always been at least one Special Lady in Hef's life. In high school, the object of his (unrequited) love was Betty Conklin. In college, his sweetheart was Millie Williams. He married Millie and expected to live happily ever after, the way people did in the movies that had shaped his images of The World As It Should Be. For the young Hefners, it didn't work out that way. Their marriage foundered -- in part due to the demands of an exacting mistress, Playboy magazine, and in part because Hef had never had a chance to sow his wild oats -- although the ten-year marriage didn't officially come to an end until 1959.

Click on the names at the right to learn more about each of the Special Ladies in Hef's romantic life.

Janet Pilgrim
Joyce Nizzari
Joni Mattis
Cynthia Maddox
Donna Michelle
Mary Warren
Barbi Benton
Karen Christy
Sondra Theodore
Heather Waite
Shannon Tweed
Carrie Leigh
Kimberley Conrad Hefner
The Foursome
The Girls Next Door
Hef's Bio
Timeline
Hef in the Media
The Playboy Philosophy

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