Hugh Hefner’s Hottest Hook-Ups

For Playboy mogul Hugh Hefner, mixing business and pleasure is a way of life. Most of the many relationships he's had over the past six decades have been with ladies who have posed for his iconic magazine. The 86-year-old is back in the headlines for his re-engagement to 26-year-old Playmate Crystal Harris, so let's take a look at some of Hugh Hefner's hottest hook-ups over the years.

Barbi Benton Benton and Hef dated for a number of years and lived together between 1969 and 1976. The two have remained close friends.

Marilyn Cole Hef never officially dated Cole, but he admitted to being "involved" with her around the time she appeared as Playmate of the Month in January 1972. Fun fact: Cole came to the attention of singer Bryan Ferry upon being named Playmate of the Year in 1973. Ferry asked her to appear on the cover of the 1973 Roxy Music album Stranded, above.

Donna Michelle The December 1963 Playmate of the Month and 1964 Playmate of the Year spent some intimate time with Hef during her Playboy tenure.

Kimberley Conrad One of only two women to actually marry Hefner (so far), Conrad got hitched to him in 1989. They had two children together before officially divorcing in 2010.

Brande Roderick The Baywatch actress was Playmate of the year in 2001, around which time she and Hef hooked up briefly.

Bridget Marquardt Marquardt dated Hef at the same time as fellow The Girls Next Door stars Holly Madison and Kendra Wilkinson, though she never made it to the coveted spot of "#1 Girl."

Holly Madison One of Hef's few non-Playmate girlfriends, Madison became his "#1 Girl" in 2001, later appearing on The Girls Next Door. The two broke up in 2008, possibly due to Hef's refusal to marry her.

Kendra Wilkinson Wilkinson became one of Hef's girlfriends in 2004 after he spotted her modeling at a Playboy Mansion party. They split after she met her husband, former NFL wide receiver Hank Baskett.

The Shannon Twins After Hef's three The Girls Next Door girlfriends all left, he was quick to recover and soon invited identical twins Kristina and Karissa Shannon to move in with him.

Crystal Harris Around the time he started dating the twins, Hef also began shacking up with Harris, to whom he proposed in December 2010. She accepted but called off the wedding five days out. They got back together in June 2012 and are now officially re-engaged. We'll see how that goes.