Women Dating Older Men
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M. Dating Older W. | W. Dating Older M. | M. Dating Taller W. | W. Dating Taller M.
They say men should half their age and add seven...
Jean Acker Born: 1978 Rudolph Valentino Born: 1895


Anna Nicole Smith Born: 1967 J. Howard Marshall II Born: 1905


Kendra Wilkinson Born: 1985 Hugh Hefner Born: 1926


Mary Murphy Born: 1931 Adolph Zukor Born: 1873


Milly D`Abbraccio Born: 1964 Roberto Rossellini Born: 1906


Janine Habeck Born: 1983 Hugh Hefner Born: 1926


Holly Madison Born: 1979 Hugh Hefner Born: 1926
Holly first caught Hef`s eye when she visited the Mansion for Midsummer Night`s Dream, the year`s most elegant party. Two days after their first date, Holly moved in but found herself vying with several other girlfriends for Hef`s attention. (He`s since downsized from seven girlfriends to three.)


Buffy Tyler Born: 1978 Hugh Hefner Born: 1926


Paris Hilton Born: 1981 Robert Evans Born: 1930


Dalene Kurtis Born: 1977 Hugh Hefner Born: 1926


Heather Kozar Born: 1976 Hugh Hefner Born: 1926


Jill St Marks Born: 1971 Telly Savalas Born: 1922
Friends only, professional acting relationship on set only. This was non-sexual
Brande Roderick Born: 1974 Hugh Hefner Born: 1926


Bridget Marquardt Born: 1973 Hugh Hefner Born: 1926


Jill Vandenberg Curtis Born: 1971 Tony Curtis Born: 1925


Judith Exner Born: 1934 Joseph Kennedy Born: 1888


Tina Jordan Born: 1972 Hugh Hefner Born: 1926


Andrea Ownbey Born: 1983 Zolar Born: 1937


Aida Yespica Born: 1982 Silvio Berlusconi Born: 1936


Jill St Marks Born: 1971 Tony Curtis Born: 1925
Professional working relationship only.