Hugh Hefner Always Dated With an Age Gap — How Old Were His Girlfriends When They Started Dating Him?

One of the things Hugh Hefner was known for before his death was his lifestyle choice to engage in relationships with beautiful women who were a lot younger than him. Hugh founded Playboy Magazine and served as the editor-in-chief for years until he passed away in 2017. The magazine was considered cutting edge and controversial, but he didn’t mind pushing the boundaries.

In fact, he even got a reality TV show out of it called The Girls Next Door for six successful seasons. The show shed light on what his relationships were like with his many young, gorgeous girlfriends. Here’s how old his six TV girlfriends were when he started dating them.

From 2002 to 2008, Bridget Marquardt was one of Hugh’s girlfriends. She's also considered one of his oldest, since she was 28 years old at the time they started dating. She was part of the Playboy brand well before the age of 28 though. When she was 25, Bridget became a Playmate in the pages of the coveted magazine before she began “dating” the man in charge. Bridget is now 48 years old.

Crystal Harris was 22 years old when she started dating Hugh in 2009. The former Playboy bunny is a travel blogger and fashion designer since she parted ways with the Playboy brand. Her blog is extremely active and filled with details about her global travels, tips & tricks, and lovely photography. Crystal is the widow of Hugh, who was still married to him at the time of his death. She is now 35 years old.

When Holly Madison started dating Hugh, it was 2001 and she was 21 years old. She was considered his “main girlfriend" at the time and they maintained their relationship until 2008. It turns out the relationship wasn’t exactly rainbows and butterflies for Holly though. She recently revealed that she feared Hugh would blackmail her with revenge porn if she ever decided to walk away from the relationship. She is now 42 years old.

When Kendra Wilkinson entered the Playboy mansion and started dating Hugh, she was barely 18 years old at the time. Keep in mind that Hugh was 78 years old that year! According to Radar Online, Kendra claims she “knew nothing about Playboy" and had recently “just graduated high school" around the time she moved into the mansion.

She recalled the first time he invited her upstairs to get intimate and revealed exactly how she responded. She said, “I was like, ‘Sure, let’s have fun.’” She also explained that before moving to the mansion, she wasn’t aware that sex would be involved in any capacity. She is now 36 years old.

Just like Kendra, Kristina and Karissa Shannon were also 18 years old when they started dating Hugh in 2008. The twin sisters didn’t stay in their relationship with the wealthy magazine founder for long though. They moved on after deciding they wanted to pursue careers in the adult movie industry instead. They are both now 32 years old.