Former Playboy bunny Zoe Gregory befriended the 44-year-old Heart FM presenter when they went to the same modelling castings in the late 1990s and when she relocated to the US to live with the late media mogul in his notorious Los Angeles home as one of his girlfriends, the magazine boss was hopeful she could introduce him to her pal.
Kelly brook
Zoe told MailOnline: "I loved Kelly to bits and, when I moved into the Mansion, Hef asked me if I knew her.
"I told him, 'Yes, we're good mates, we used to go to castings together.'
"I invited her over a few times and Kelly did seem keen at first, but then she told me she didn't want to get involved.
"I think it was because she was in a relationship and her agency talked her out of going in that direction. She was trying to maintain a good reputation for her career.
"Also, she might have seen the backlash Katie Price got after modelling for Playboy and thought, I'm not going to do it."
Zoe thinks not only would Kelly have been "perfect" for Playboy, she even believes Hefner - who died in 2017 aged 91 - would have wanted to marry her.
She said: "But I have always wondered why she didn't go down that path. She would have been perfect for Playboy and moving to the States would have been a big boost for her career.
"She would have stood out as a brunette at a time when there was a bit of a blonde invasion with Pamela Anderson and Anna Nicole Smith.
"Hef would have loved Kelly over and, knowing him as I do, I'm sure he would have married her. She was the polar opposite of what he had at the Mansion, which was all blonde hair and big t**s."
The 'From Britain to Bunny' author - who lived in the Mansion for three years and became Hefner's number two girlfriend until she was forced to leave in 2004 after falling out with another of his lovers, Holly Madison - also revealed her former lover was "obsessed" with Katie Price and wanted her to move into his house too.
She said: "Hef loved Katie, he was obsessed with her. He wanted her to move in permanently and be his girlfriend, but she had just had Harvey so she couldn't.
"She is naturally outspoken and never shy and when she's had a couple of drinks it gets times 10.
"I don't remember much from her visits because we would party hard whenever she was there."
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