2010 - Present
Hugh popped the question on Christmas Eve, 2010 and gave the Playmate a big diamond ring.
February 2009 - December 2010
Hugh and Crystal met on Halloween of 2008. They started dating in early 2009 and became his 'number one girlfriend...
January 2009 - January 2009
Bikini model Jenna Bentley was linked to the ultimate Playboy Hugh Hefner in 2009.