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Hugh Hefner, Crystal Harris

In 2008, Hefner met Crystal Harris at his annual Halloween bash at the mansion. Just months later she moved in – along with the Shannon Twins – and quickly slipped into the role of No. 1 girlfriend. While Madison couldn’t get Hefner to commit to marriage, Harris could. Hefner popped the question over Christmas in 2010 and she said yes. However, the road to the altar wasn’t smooth. Weeks before their June 2011 wedding, Harris called it off – and left Hefner red faced as he had already put her on the cover of the June issue of Playboy with the headline, "Introducing America's Princess, Mrs. Crystal Hefner." Oops! Although he swore off marriage (again!), he reunited with Harris a year later and in early December 2012 they announced that they were once again engaged. The star-studded nuptials are set to take place at the mansion on New Year’s Eve – though, as we’ve learned, anything can happen.

Hugh Hefner's Many Exes

Before Playboy mogul Hugh Hefner takes a trip to the altar to marry on-again, off-again girlfriend Crystal Harris, take a trip down memory lane with omg! as we look back at some of Hef's gal pals from over the years.

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