Hugh Hefner Was Known for Having Multiple Girlfriends at All Times

Fans of The Girls Next Door might remember Hugh Hefner as a lovable older man who just happened to have a trio of girlfriends flanked on either side of him at all times. But why did Hugh Hefner always have three girlfriends at once?

The A&E docuseries Secrets of Playboy dives into the details surrounding Hugh's life in the Playboy Mansion and the dynamic between him and all of the women who came through its doors.

Members of Hugh's inner circle and former girlfriends are interviewed in the docuseries. There seems to be an understanding that at different points in his life, Hugh had three main girlfriends at once, even if those women changed relatively often. However, while he always brought the three with him, he had others who were rarely seen.

As most know, three of his main girlfriends, Holly Madison, Bridget Marquardt, and Kendra Wilkinson starred with him on The Girls Next Door.

Even before their time came with the Playboy magnate, Hugh had different trios of women who were considered his main girlfriends apart from anyone else he might have had relations with at the Playboy Mansion.

In the final season of The Girls Next Door, Hugh and the original three women split up. He replaced them with three new girlfriends — Crystal Hefner (nee Harris) and twins Kristina and Karissa Shannon.

So, why did he always have three women on his arm? Well, Hugh has never talked about it outright — throughout his time as a public figure, it just became something he was unspokenly known for. Maybe it was a way to ensure that he always had one of his three main women by his side in case the other two were unavailable, or it was about something more intimate taking place behind closed doors.

Before his 2017 death, Hugh was married three times. He married his first wife, Mildred Williams, in 1949; they divorced in 1959. In 1989 he married Playmate of the Year Kimberley Conrad. Although they separated in 1998, they didn't officially get divorced until 2010. During their separation and after the divorced was finalized, Hugh continued dating women.

In fact, it was during the separation that part of The Girls Next Door was filmed. Hugh got married for a third and final time in 2012. This time, it was to Playmate Crystal Harris, whom he remained married to until he died in 2017.

Holly is featured in the Secrets of Playboy docuseries, but it isn't the first time she shared details of her time at the Playboy Mansion with Hugh and his other girlfriends.

In a 2021 interview on the Call Her Daddy podcast, Holly admitted that she now views her relationship with Hugh as a "was a very Stockholm syndrome type of thing." She also said that when she lived at the Playboy Mansion, it had a "cult-like atmosphere."

And there are similar sentiments echoed in the Secrets of Playboy docuseries.

Watch Secrets of Playboy on Mondays at 9 p.m. EST on A&E.