All of Hugh Hefner's past and present girlfriends and wives. The ultimate playboy, Hefner has dated tons of women, most of them Playboy bunnies who he discovered. This long list of lovers and exes covers an entire lifespan yet the women seem to always be young. Hugh Hefner has only been married a couple times but he's dated continuously. Not that it's unexpected, but some of the gorgeous women on Hugh's arm have been caught on celebrity sex tapes with other high-profile men. Kendra Wilkinson, for example, is high on the list of celeb sex tapes and is no stranger to the attention. As of now, Heff himself has not been in the middle of a celebrity sex tape scandal, but who knows what the wily old man will get up to next? Here are all the playmates Hefner's been official with (who knows how many are "unofficial").
Check out this list of Hugh Hefner girlfriends and Hugh Hefners wife (or Hugh Hefener wives).
Hugh Hefner's Loves & Hookups,
Brande Roderick
Hugh Hefner hooked-up with Brande Roderick from 1999 - 2000.
Bridget Marquardt
Hugh Hefner counted Bridget Marquardt as one of his girlfriends from 2002 - 2008.
Holly Madison
Holly Madison was one of Hugh Hefner's girlfriends from 2001 - 2008.
Kendra Wilkinson
Kendra Wilkinson was in a relationship with Hugh Hefner from 2004 - 2008.
Kimberley Conrad
Hugh Hefner was married to Kimberley Conrad from 1989 - 2010.
Shannon Tweed
Shannon Tweed was reportedly one of Hugh Hefner's girlfriends from 1981 - 1983.
Crystal Harris
Hugh Hefner dated Crystal Harris on-and-off since 2008. The couple tied the knot in 2012.
Kristina Shannon
Hugh Hefner was romantically involved with Kristina Shannon from 2008 - 2010.
Anna Sophia Berglund
Hugh Hefner was involved with Anna Sophia Berglund in 2011.
Jenna Bentley
Hugh Hefner was reportedly hooking up with Jenna Bentley in 2009.