Most of the general public is fascinated by Hugh Hefner; most men envy him and see him as some sort of hero.

Women find him attractive due to his money, fame, and sex appeal, and even those who don’t feel this way about Hef still find him to be very interesting.

His ideals on sexual curiosities and interests were not well thought of in his earlier years, as he was at times a topic of controversy. Luckily times have changed.

Though he’s 83 years old, he has no shortage of girlfriends and is able to pull off what many men have been trying to successfully do for years - dating more than one woman at a time!

Here is a LONG list of Hef’s girls throughout the years.

Mildred Williams

Date of Birth

10 March 1926, Chicago, Illinois, USA

Nickname

Millie. Mildred Williams

Born: March 10, 1926
Married to Hefner: 1949 to 1959
Miscellaneous Information: Hugh met her in college at Northwestern University

Spouse

Hugh M. Hefner	(25 June 1949 - 1959) (divorced) 2 children
Edwin Gunn	(? - present) (separated)

Trivia

Mother of Christie Hefner and David Hefner. Her second husband, Edwin Gunn, adopted them, but the children changed their names back to Hefner after Mildred and Gunn separated.
First wife of Hugh M. Hefner.
Ex-sister-in-law of Keith Hefner.

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Kimberley Conrad


Born	August 6, 1962 (1962-08-06) (age 48) Moulton, Alabama, U.S.
Spouse	Hugh Hefner (m. 1989–2010) (divorced); 2 children

Kimberley Conrad (born Kimberley Conradt on August 6, 1962) is an American model and actress.

Kimberley Conrad
Playboy centerfold appearance
January 1988
Preceded by	India Allen
Succeeded by	Kari Kennell
Playmate of the Year
1989
Preceded by	India Allen
Succeeded by	Renee Tenison
Personal details
Measurements	Bust: 36" Waist: 24" Hips: 36"
Height	5 ft 9 in (1.75 m)
Weight	122 lb (55 kg; 8.7 st)

Conrad was chosen as Playboy's Playmate of the Month in January, 1988 and became Playmate of the Year 1989. Conrad was born in Alabama and raised in Nevada and British Columbia.

Personal life

She is probably best known for marrying Playboy founder Hugh Hefner in July 1989, an event which sparked worldwide media attention. The comic strip Doonesbury referred to the event as the belated end of the 1970s. The Hefners had two sons together: Marston Glenn Hefner (shares birthday with his father: April 9, 1990) and Cooper Bradford Hefner (September 4, 1991). After nine years of marriage, Conrad and Hefner separated although remained married. Hugh Hefner was quoted, "I would've been happy to divorce her when we separated, but she wanted to remain married for our boys."^[1] Conrad then moved into a house next door to the Playboy Mansion. After an 11 year separation, Hefner filed for divorce stating irreconcilable differences in September 2009 after his youngest child turned 18;^[1] the divorce was finalized in March 2010.^[2]
Conrad is a vegetarian and has worked with PETA.^[3]

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Crystal Harris



Playboy centerfold appearance
December 2009
Preceded by	Kelley Thompson
Succeeded by	Jaime Faith Edmondson
Personal details
Born	April 29, 1986 (1986-04-29) (age 24) Lake Havasu City, Arizona^[1]^[2]
Measurements	Bust: 34D^[2] Waist: 25 Hips: 35
Height	5 ft 6 in (1.68 m)^[2]
Weight	124 lb (56 kg)

Crystal Harris (born April 29, 1986)^[1] is an English born American^[1] model and singer who was the Playboy Playmate of the Month for December 2009.^[2] On December 24, 2010, she became engaged to Hugh Hefner, to become his third wife.^[3]
Harris' British parents were entertainers, who were working at the England-themed amusement park in Lake Havasu City, Arizona, the present location of the 19th century London Bridge. After her birth, they returned to England, before returning to the United States and settling in San Diego, California, where she and her two elder sisters grew up.^[1]
Harris attended La Jolla High School and went to San Diego State University, majoring in psychology,^[1] where she started modelling. It was during this period that she came to the attention of the Playboy organization.

Harris met Hugh Hefner on Halloween 2008.^[1] She then appeared as "Co-Ed of the week" on Playboy.com magazine in the week of October 30, 2008, under the name Crystal Carter.^[4] From late 2009 Harris has appeared in E!'s The Girls Next Door.^[5]
In January 2009, she started dating Hugh Hefner,^[6] joining the Shannon Twins after his previous number one girlfriend Holly Madison left him.^[7]
In April 2010, Harris signed a recording contract with Organica Music Group, a label run by producer Michael Blakey.^[8] Crystal Harris was first exposed to the entertainment industry through her late father, Ray Harris, who was a singer and songwriter.^[9]
Harris also appeared in an episode of The Hills in season 2.