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The Many Loves Of Hugh Hefner

Lifelong ladies man Hugh Hefner finally married Crystal Harris on New Year's Eve. In honor of their recent nuptials, let's take a look at the other ladies in Hef's past.

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Playboy founder Hugh Hefner has had countless lovers over the years — some more notable than others. Here's a chronological history of the wives, girlfriends, and Bunnies who found themselves in his bed. Because Hef has never been a one-woman man, there's a lot of overlap.

Mildred Williams (1949-1959)

Hef married his first wife in 1949. Mildred cheated on Hugh while he was in the Army, but she later gave him a free pass for sleeping with other women.

Barbi Benton (1969-1976)

Partnered for eight years, Barbi and Hugh met on the set of Playboy After Dark. Hef later said that meeting Barbi was his favorite memory of doing the show.

Lillian Muller (c. 1974-1976)

When not dating Hugh Hefner, Lillian made her mark in the music video world, appearing in Van Halen's "Hot For Teacher" and Rod Stewart's "Da Ya Think I'm Sexy?"

Kimberley Conrad (1989-2010)

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Hugh's longest marriage was to Kimberley Conrad, with whom he had two sons. They separated after nine years but stayed married until 2010.

Izabella St. James (2002-2004)

Polish Playmate Izabella is best known for writing a tell-all memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion, the first book written by one of Hugh's exes.

Bridget Marquardt (2002-2008)

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One of the Girls Next Door, Marquardt was never actually a Playboy Playmate. There are still plenty of nude pictures of her online.

Holly Madison (2003-2008)

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Another one of the Girls Next Door, Holly broke up with Hef because he wouldn't put a ring on it. She has since moved on to other reality TV endeavors.

Kendra Wilkinson (2004-2009)

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Kendra lasted longer than the other Girls Next Door, but she and Hugh eventually parted ways. Now going by her married name Kendra Baskett, her current series is Kendra on Top.

Kristina and Karissa Shannon (2009-2010)

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Along with Crystal Harris, Kristina and Karissa were Hef's rebounds after his break-up with Holly. They also appeared on The Girls Next Door.

Crystal Harris (2009-2011, 2012-)

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Crystal and Hugh have been on-again, off-again, but now they're officially married. Their New Year's Eve wedding was held at the Playboy Mansion.

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