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Hugh Hefner, founder of Playboy, married three times. In order, his wives were Mildred “Millie” Williams, Kimberley Conrad, and Crystal Harris, who later took the name Crystal Hefner. Each relationship began in a different setting: Williams was a Northwestern University classmate, Conrad first met him during a 1988 photo session at the Playboy Mansion, and Harris met him at a Halloween party at the mansion in 2008. The sections below cover each woman’s first meeting, the time between meeting and marriage, and where the published accounts disagree.
The three wives at a glance
| Order | Wife | How they first met | Meeting to marriage | Marriage |
|---|---|---|---|---|
| First | Mildred “Millie” Williams | Northwestern University classmates (the sources do not give a date for their first meeting) | Not stated | Married 1949; ended in the late 1950s. CBS’s 2017 obituary gives 1958; The Daily Beast’s 2026 retrospective gives 1959. |
| Second | Kimberley Conrad | Visited the Playboy Mansion for a photo session in January 1988 and became acquainted with Hefner there | About 18 months (January 1988 to July 1989) | Married July 1989. How and when the marriage ended is not stated in the sources cited here. |
| Third | Crystal Harris (later Crystal Hefner) | Halloween party at the Playboy Mansion, 2008 | About 4 years 2 months (Halloween 2008 to 31 December 2012), including a called-off 2011 wedding | Married New Year’s Eve 2012; remained his wife until his death in 2017 |
Mildred “Millie” Williams: the first wife
Williams was Hugh Hefner’s first wife. The retrospective account available for this article describes the two as Northwestern University classmates, and they married in 1949. Because the sources are brief on this period, the story of how the relationship developed in college is not documented in detail.
Their marriage ended in the late 1950s. The reports disagree on the exact year: CBS’s 2017 obituary gives 1958, while The Daily Beast’s 2026 retrospective gives 1959. Readers who need a precise date should treat either year as a reported figure rather than a settled one.
Kimberley Conrad: the second wife
Kimberley Conrad’s meeting with Hefner is the best documented of the three. The Washington Post’s 1989 wedding report says she came to the Playboy Mansion for a photo session in January 1988, and that she became acquainted with Hefner on that visit.
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According to the same report, Hefner invited her to a movie screening. She declined, explaining that she did not want to be a “one-night stand.” A few months later, he asked her to become his “Playmate for life.” The couple married in July 1989. The Washington Post account is contemporaneous with the wedding, which makes it more reliable than later summaries that repeat the story without a source.
Crystal Harris: the third wife
Crystal Harris met Hefner at the Playboy Mansion’s Halloween party in 2008. An Entertainment Tonight report from 2011 says she moved into the mansion two weeks after that party.
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The couple planned to marry in 2011, but Harris called off the wedding shortly before it was to take place. They later reconciled and married on New Year’s Eve 2012. She remained his wife until his death in 2017. Harris is also known as Crystal Hefner, and both names refer to the same person.
The Guardian’s 2024 interview, connected to her memoir, is one of the later first-person accounts of her time in the household. Her recollections there are her own perspective and should be attributed to her rather than presented as independently verified fact. Her memoir, Only Say Good Things: Surviving Playboy and Finding Myself, is the natural next read for readers who want her full account in her own words.
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Keeping the three stories apart
Three distinct milestones are easy to confuse in this story: meeting, engagement or dating, and marriage. Williams’s account is a school connection, Conrad’s is a photo-session visit followed by a movie invitation and a proposal, and Harris’s is a party meeting that led to her moving into the mansion before the marriage. The published accounts describe how each relationship began. They do not establish the private dynamics of any of the marriages, and this article does not take a position on disputed personal recollections.
For a clear timeline, use the order of marriages (1949, 1989, 2012) and the setting of each first meeting rather than trying to date the courtship in months.
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