Hugh Hefner’s Harem: A Look at the Girlfriends from Past to Present

• John Fitzgerald
• Wednesday, May 27, 2009

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

Born: March 10, 1926
Married to Hefner: 1949 to 1959
Miscellaneous Information: Hugh met her in college at Northwestern University. Pictures of her are non-existent!

Janet Pilgrim

Born: June 13, 1934
Dated Hefner: Some time in the 1950s
Occupation: Model
Miscellaneous Information: She was Playmate of the Month in July and September of 1955 and again in October 1956.

Joni Mattis

Born: November 28, 1938
Died: September 4, 1999
Dated Hefner: 1960 to 1961
Occupation: Model
Miscellaneous Information: She was Playmate of the Month in November 1960.

Joyce Nizzari

Born: May 20, 1940
Dated Hefner: Some time in the early 1960s
Occupation: Model, dancer, and actress
Miscellaneous Information: Nizzari was Playmate of the Month in December 1958.

Cynthia Maddox

Born: April 24, 1905
Dated Hefner: Some time in the early 1960s
Occupation: At first, she worked as a secretary at the main office in Chicago, but worked her way up to assistant cartoon editor of Playboy magazine. She also posed for Playboy many times.
Miscellaneous Information: She broke up with Hef when she learned that he didn’t want to marry her.

Donna Michelle

Born: December 8, 1945
Died: April 9, 2004
Dated Hefner: 1963
Occupation: Model, actress, and photographer
Miscellaneous Information: Donna Michelle was Playmate of the Month in December 1963 and became the Playmate of the Year in 1964.

Gale Olson

Born: October 27, 1947
Dated Hefner: 1966 to 1969
Occupation: Model
Miscellaneous Information: She was Playmate of the Month in July 1968.

Mary Warren

Dated Hefner: In the mid 1960s
Occupation: Model

Carol Imhof

Born: March 13, 1948
Dated Hefner: 1970
Occupation: Model; Worked at the Playboy Club in Chicago
Miscellaneous Information: She was Playmate of the Month in December 1970. Imhof was also he 200th Playmate.

Suze Randall

Born: May 18, 1946
Dated Hefner: In the 1970s
Occupation: Photographer, pornographer
Miscellaneous Information: She worked for Playboy magazine in the 1970s and is still an active pornographer.

Barbie Benton

Born: January 28, 1950
Dated Hefner: 1971 to 1974
Occupation: Model, actress, singer
Miscellaneous Information: Barbie Benton was never Playmate of the Month, though some people think she was at some point because she appeared on the cover of the magazine several times.

Karen Christy

Born: March 11, 1951
Dated Hefner: 1971 to 1976
Occupation: Model
Miscellaneous Information: She was Playmate of the Month in December 1971.

Marilyn Cole

Born: May 7, 1949
Dated Hefner: 1972 to 1974
Occupation: Model
Miscellaneous Information: Cole was Playmate of the Month in January 1972.

Daina House

Born: December 30, 1954
Dated Hefner: 1976
Occupation: Model
Miscellaneous Information: House was Playmate of the Month in January 1976.

Lillian Müller

Born: August 19, 1952
Dated Hefner: 1976 to 1977
Occupation: Television and film actress, model
Miscellaneous Information: she was Playmate of the Year in 1976.

Patti McGuire

Born: September 5, 1951
Dated Hefner: 1976 to 1977
Occupation: Model
Miscellaneous Information: McGuire was Playmate of the Month in November 1976 and was Playmate of the Year in 1977.

Sondra Theodore

Born: December 12, 1956
Dated Hefner: 1977 to 1980
Occupation: Television and film actress, model
Miscellaneous Information: Sondra Theodore was Playmate of the Month in July 1977.

Heather Waite

Dated Hefner: 1978
Occupation: Former Playboy mansion secretary

Candy Loving

Born: September 4, 1956
Dated Hefner: 1978
Occupation: Model
Miscellaneous Information: Loving was Playmate of the Month in January 1979. She was also rated #6 in Playboy’s Top 100 Playmates, published in 2000.

Terri Welles

Born: November 21, 1956
Dated Hefner: 1980 to 1981
Occupation: Actress, model
Miscellaneous Information: She was Playmate of the Year in 1981.

Shannon Tweed

Born: March 9, 1957
Dated Hefner: 1981 to 1983
Occupation: Canadian actress, model
Miscellaneous Information: Tweed was Playmate of the Month in November 1981 and was Playmate of the Year in 1982.

Carrie Leigh

Born: August 25, 1963
Dated Hefner: 1983 to 1987
Occupation: Former model, founder of Nude magazine (2007)

Marina Baker

Born: December 8, 1967
Dated Hefner: 1987 to 1988
Occupation: Former model and actress; currently a journalist and children’s book author; also a politician in England
Miscellaneous Information: Marina was Playmate of the Month in March 1987. She now goes by the name Marine Pepper in her journalism, author, and political days.

Kimberley Conrad

Born: August 6, 1962
Married Hefner: 1989 to 1999
Occupation: Model
Miscellaneous Information: She was Playmate of the Month in January 1988 and made Playmate of the Year for 1989.

Amanda Bentley

Born: May 18, 1978
Dated Hefner: 1999 to 2000
Occupation: Model
Miscellaneous Information: Amanda was on the cover of the May 2000 issue of Playboy with twin sister Sandy.

Brande Roderick

Born: June 14, 1974
Dated Hefner: 1999 to 2000
Occupation: Model, film and television actress
Miscellaneous Information: In 1998 and 1999, Brande Roderick was in erotic film. In 2000, she played the role of Leigh Dyer on the hit TV show Baywatch. Also, Roderick was Playmate of the Month in April 2000 and Playmate of the Year in 2001.

Sandy Bentley

Born: May 18, 1978
Dated Hefner: 1999 to 2000
Occupation: Model, television actress; no prominent roles in acting yet, but she’s made some guest appearances
Miscellaneous Information: Sandy was on the cover of the May 2000 issue of Playboy with twin sister Amanda.

Heather Kozar

Born: May 4, 1976
Dated Hefner: 1999 to 2001
Occupation: Model
Miscellaneous Information: Heather Kozar was Playmate of the Month in January 1998 and Playmate of the Year in 1999. She was also the St. Pauli Girl for 2002. She was even more well known for being one of Barker’s Beauties on the daytime television game show The Price Is Right.

Jill St. Marks

Born: November 22, 1971
Dated Hefner: 2000
Occupation: Model

Buffy Tyler

Born: April 18, 1978
Dated Hefner: 2000 to 2001
Occupation: Model
Miscellaneous Information: She was Playmate of the Month for November 2000.

Katie Lohmann

Born: January 29, 1980
Dated Hefner: 2000 to 2001
Occupation: Model and film actress
Miscellaneous Information: Lohmann was Playmate of the Month for April 2001.

Jessica Paisley

Dated Hefner: 2000 to 2002
Occupation: Model

Kimberley Stanfield

Born: November 18, 1981
Dated Hefner: 2001
Occupation: Model
Miscellaneous Information: Kimberly was Playmate of the Month for July 2001.

Regina Lauren

Born: August 8, 1975
Dated Hefner: 2001
Occupation: Model and television personality
Miscellaneous Information: Regina Lauren was on 5 episodes of Howard Stern’s television show in 2001. She was also on Stern’s radio show one time. Additionally, Lauren has hosted some documentaries on the Playboy Mansion.

Stephanie Heinrich

Born: November 13, 1979
Dated Hefner: 2001
Occupation: Model and actress
Miscellaneous Information: She was Playmate of the Month for November 2000.

Christi Shake

Born: August 22, 1980
Dated Hefner: 2001
Occupation: Model and actress
Miscellaneous Information: Christi was Playmate of the Month for May 2002 and has also been in several Playboy videos.

Sandee Westgate

Born: May 5, 1979
Dated Hefner: 2001
Occupation: Model
Miscellaneous Information: She was Playboy’s Cyber girl of the week for the first full week in December in 2001.

Cathi O`Malley

Born: July 27, 1981
Dated Hefner: 2001 to 2002
Occupation: Model
Miscellaneous Information: Cathy was Playboy’s Cyber girl of the week for the third week of February 2002.

Dalene Kurtis

Born: November 12, 1977
Dated Hefner: 2001 to 2002
Occupation: Model and television personality
Miscellaneous Information: Kurtis was Playmate of the Month for September 2001 and was also the Playmate of the Year for 2002.

Michelle Winchester

Dated Hefner: 2001 to 2002
Occupation: Model

Renee Sloan

Born: December 24, 1972
Dated Hefner: 2001 to 2002
Occupation: Model, stunt woman, and actress
Miscellaneous Information: Renee Sloan is currently married to actor Scott Baio.

Charis Boyle

Born: December 31, 1976
Dated Hefner: 2001 to 2003
Occupation: Model
Miscellaneous Information: Charis Boyle was Playmate of the Month for February 2003. She was also Playboy’s Cyber Girl of the Week in August 2001.

Cristal Camden

Born: September 7, 1981
Dated Hefner: 2001 to 2003
Occupation: Model
Miscellaneous Information: Cristal has appeared on the television show The Girls Next Door.

Tiffany Holiday

Born: January 20, 1986
Dated Hefner: 2001 to 2003
Occupation: Playboy model and porn star

Tina Jordan

Born: August 21, 1972
Dated Hefner: 2001 to 2003
Occupation: Model and actress
Miscellaneous Information: She was Playmate of the Month for March 2002.

Tricia Wertz

Dated Hefner: 2001
Occupation: Model (she’s the one in the orange)

Teri Harrison

Born: February 16, 1981
Dated Hefner: 2002
Occupation: Former Hooters restaurant employee; currently a model and an actress
Miscellaneous Information: Harrison was Playmate of the Month for October 2002.

Stacy Burke

Born: May 27, 1975
Dated Hefner: 2002
Occupation: Model and porn star

Izabella St. James

Born: September 25, 1975
Dated Hefner: 2002 to 2004
Occupation: Writer and actress
Miscellaneous Information: Izabella St. James is the author of the book Bunny Tales: Behind Closed Doors at the Playboy Mansion which was published in August 2006.

Lana Kinnear

Born: July 29, 1976
Dated Hefner: 2002 to 2004
Occupation: Model, actress, and dancer

Zoe Paul

Born: February 15, 1974
Dated Hefner: 2002 to 2004
Occupation: Actress
Miscellaneous Information: Zoe Paul plays in the Lingerie Women’s Football Bowl for the New York Euphoria.

Holly Madison

Born: December 23, 1979
Dated Hefner: 2002 to 2008
Occupation: Model and television personality
Miscellaneous Information: Aside from hanging out in the playboy mansion and posing for Playboy, Holly’s latest adventure was that she was on Season 8 of Dancing with the Stars.

Bridget Marquardt

Born: September 5, 1973
Dated Hefner: 2002 to 2008
Occupation: Model, film actress, and television personality

Sheila Levell

Dated Hefner: 2003 to 2004
Occupation: Actress, television personality, and dancer
Miscellaneous Information: Sheila was the Playboy Cyber Girl of the Week for the first week in July 2004.

Kendra Wilkinson

Born: June 12, 1985
Dated Hefner: 2004 to 2008
Occupation: Model, television personality, and music video personality
Miscellaneous Information: Kendra is on the E! Network show The Girls Next Door.

Janine Habeck

Born: June 3, 1983
Dated Hefner: 2006 to 2008
Occupation: Model
Miscellaneous Information: Janine was Playmate of the Month for September 2006.

Crystal Harris

Dated Hefner: 2008 to present
Occupation: Model

Dasha Astafieva

Born: August 4, 1985
Dated Hefner: 2008 to present
Occupation: Ukrainian model
Miscellaneous Information: Dasha was Playmate of the Month for January 2009.

Karissa & Kristina Shannon

Born: April 7, 1989
Dated Hefner: 2008 to present
Occupation: Model
Miscellaneous Information: both appeared on the television show The Girls Next Door.

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