Entertainment

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

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.

hef1 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present 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

janet pilgrim Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

joni mattis Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

joyce nizzari Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

cynthiamaddox Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

donna michelle Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

gale olson Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Mary Warren

mary warren Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

Dated Hefner: In the mid 1960s
Occupation: Model

Carol Imhof

carol imhof Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

suze randall Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

barbie benton Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

karen christy Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Marilyn Cole

marilyn cole Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Daina House

daniahouse Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Lillian Müller

llianmuller Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

pattimcguire Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

sondratheodore Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

heatherwaite Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

Dated Hefner: 1978
Occupation: Former Playboy mansion secretary

Candy Loving

candyloving Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

terri welles Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Shannon Tweed

shannon tweed Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

carrieleigh Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Marina Baker

marinapepper Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

kimberley conrad Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

amandabently Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

brande roderick 300x225 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

sandybently Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

heather kozar 200x300 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

jill st marks 197x300 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Buffy Tyler

buffy tyler 220x300 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Katie Lohmann

katie lohmann Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

jessica paisley 200x300 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

Dated Hefner: 2000 to 2002
Occupation: Model

Kimberley Stanfield

kimberlystanfield Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Regina Lauren

reginalauren Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

stephanie heinrich 300x185 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Christi Shake

christi shake Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

sandee westgate Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

cathyomally Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

dalene kurtis Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

michellewinchester1 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

Dated Hefner: 2001 to 2002
Occupation: Model

Renee Sloan

reneesloan1 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

charis boyle Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

cristal camden Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

tiffanyholiday Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Tina Jordan

tina jordan Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

triciawerttz Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Teri Harrison

teri harrison Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

stacy burke Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Izabella St. James

isabellastjames1 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

lana kinnar Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Zoe Paul

zoepaul1 Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

holly madison Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

bridget marquardt Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Sheila Levell

sheilalevell Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

kendra wilkinson Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

janiehabeck Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Crystal Harris

crystal harris Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

Dated Hefner: 2008 to present
Occupation: Model

Dasha Astafieva

dasha astafieva Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

karissakristinashannon Hugh Hefners Harem: A Look at the Girlfriends from Past to Present

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

Leave a Comment

  1. joe says:

    well..I never thought today could get any more depressing, and there ya go.

  2. Barry says:

    Nice list, seems like the only three with real occupations are Kendra and Bridget (with their television shows) and fine art photographer/publisher Carrie Leigh (with Nude Magazine) wonder what the rest of them are really up to.

  3. jman says:

    he went to Illinois, not NU. but a great resume nonetheless.

    • sarah says:

      he got his BA at the university of illinois and attended graduate school at northwestern university for one semester.

  4. Mark says:

    i knew he had a thing for blondes, but… wow!

  5. mary says:

    i think you got some fo the dates wrong…

  6. Playmate says:

    You're missing many girls. Hef never dated Janine or Dasha. TOTALLY FALSE.

  7. Natalie says:

    sick!!! He could be the twins great grandfather!

  8. pootie tang says:

    I seriously hope the date is wrong on Tiffany Holiday because it says he was dating her when she was 15-17 years old!

  9. tiffsfan says:

    tiffany holiday was not a porn star, thats someone different. this one is just a model, and her birthday is wrong. shes 28 now, not 22.

  10. MMO says:

    Warren was the best, hands down.

  11. MFL Lingerie says:

    I’ve recently started a blog, the information you provide on this site has helped me tremendously. Thank you for all of your time & work.

  12. angelique says:

    wow…. no black women??!! lol

  13. stew says:

    skum prostitutes money for sex

  14. Pariuri says:

    Gorgeous girls, but no black women ?!

  15. Smoothchic says:

    60 women???? D guy is already dead inside.

  16. James says:

    He had to be Jesus reincarnated. If you went through what He went through, why not?

  17. intheknow2010 says:

    sandee westgate is a pornstar. not tiffany and her age is wrong. hef never dated dasha or janine. Also there are a few missing and then there are some who do have current occupations that are not listed.

  18. wondering_why says:

    I was one of the above's boyfriend and later husband combined for nearly 7 years starting in high school then college. Just as handsome as she was attractive with an athletic body and a brain to match. The entire issue is more than disturbing! Divorced 10 months after she started working for the local club. In comparison its like a 20 year old clunker parked on the new sports car lot. What makes a women want to be known for this? No one I know or knew us as a couple can even imagine her doing this. (about 5,000 or so)If there was no money involved this page would have one or two pictures of girls none want to see, wouldn't it? How shallow can people be!

  19. http://amog.com says:

    what a collection, thank's for sharing this!it'a great post!

  20. fullbet says:

    Very nice Karissa and Kristina Shannon. Thanks

  21. Thanks for sharing these info with us! I was reading something similar on another website that i was researching. I will be sure to look around more. thanks&

  22. miere albine says:

    This i can say that was a golden live. Now i think he can do anything to that young girl, but it was the best in his life.

  23. This is a lucky man. But i think that now is too old for some of his womens.

  24. Giorgio says:

    My list is a little shorter with only 49 counting and my girls are multinational. I am 49.
    He has no Indian woman experience on his resume, he has no idea what he was missing.
    While blondes are somehow attractive in their stupidity, I would prefer a Chinese long legged girl with slim body and silky skin.
    But, hey, Hef, keep up the good work, is all fun.

  25. janyloyal says:

    Nice Postings under discussion. I really like it.

  26. Guest says:

    Who is the tall blonde all the way to the left in the Tricia Wertz picture?

  27. kendra says:

    Goes to show how Latina girls, Asian girls and black girls have enough class to not date some old perverted man for fame.

  28. James says:

    Hmm, it appears to me that he has an emptiness inside that no matter how hard he tries… he can't fill.

  29. whst a nice girls…

  30. www.pcultau.ro says:

    what a huge colection, and only beautifull women.

  31. premierleaguebg says: