Because Hef has never been a one-woman man, there's a lot of overlap.
This long list of lovers and exes covers an entire lifespan yet the women seem to always be young.
We get that they're twins, but we were still a little bummed out to hear that Hugh Hefner can't tell two of his three girlfriends apart.
Honestly, if you look quickly at a photo of Hef's latest batch of ladies, it's even a bit hard to distinguish 22-year-old Crystal Harris from the 19-year-old Shannon sisters.
Photo gallery: See Hef's girlfriends through the years.
Barbi Benton Back in 1968 it was only kind of creepy that 42-year-old Hugh Hefner was dating an 18-year-old.
The playboy, who claims he is ‘not your average 74 year old’ says it’s all in the name of true love.
Whitney flies ladies as young as 25 to his luxurious house for the weekend to be fine dined and wooed.He’ll often throw in a gift of lingerie from Victoria’s Secret as well.Whitney even gives his guests a bonus of £200 (£140) just for making the trip. I work out four times a week and used to do Ironman triathlons.But when a teenage extra named Barbara Klein started "acting" like Hef's girlfriend during episodes of the series "Playboy After Dark," she soon found herself cast in the real-life role, too.Her new beau suggested she change her name to Barbi Benton, and a '70s pop-culture icon was born.