Playboy founder Hugh Hefner (1926 – 2017) has died at the age of 91, and it’s the end of an era. Although he was famous for always having a string of blonde, buxom women at his side, he seemed particularly fond of marriage, and went down the aisle three times in his life. Let’s take a look back.

Millie Williams: 1949-1959

In 1949, Hugh married Northwestern University student Mildred ("Millie") Williams. It was the only time he married a woman his age - they were both 26. They had two children, Christie and David. Before the wedding, Mildred confessed that she had an affair while he was away in the army. He called her confession "the most devastating moment of my life." Mildred allowed him to have sex with other women, out of guilt for her infidelity, hoping that it would preserve their marriage. Unfortunately, it didn’t work out - the two were divorced in 1959.

Kimberley Conrad: 1989-2010

Hugh spent the next few decades living it up, taking plenty of lovers (most of whom were Playboy Bunnies) and generally being a bon vivant. After having a stroke in 1985, he toned down his decadent lifestyle, and remarried in 1989. His new wife was Playmate of the Year Kimberley Conrad; they were 36 years apart in age. The couple had two sons: Marston Glenn and Cooper Bradford, and the infamous Playboy Mansion became a family-friendly home. After he and Kimberley separated in 1998, she moved into a house next door to the mansion. However, they remained legally married for several years.

Crystal Harris: 2012-2017

In January 2009, 23-year-old Crystal Harris started dating Hugh Hefner, who was 60 years her senior, joining the Shannon Twins after his previous "number one girlfriend", Holly Madison, had ended their seven-year relationship. They got engaged in 2010, but Crystal broke off their engagement five days before their planned wedding. The two later reconciled, and on December 31, 2012, Harris and Hefner married at the Playboy Mansion in a small private ceremony; he was 86 and she was 26. She remained married to Hugh until his death in 2017.