Hugh hefner dating

While she is still a jaw-dropping beauty, she was a bit softer and more refined than a lot of the girls Playboy photographed in the late 80’s and 90’s, perhaps showing return to the type of girl (aka the real girl) that made the magazine famous in the first place.

was never actually a Playmate and only posed in the magazine after the show blew up.

She’s perhaps one of the more famous Playmates; she had a semi-serious career starring in multiple films (Hollywood and Bollywood). Either way she was the perfect women to transition Playboy into a new millenium.

And unlike Pamela Anderson — who personified the magazine in the early 90’s — Hef slept with her.

So, she makes this list because of that and because she is a beautiful young girl who at least didn’t (originally) marry him just for his money.

With him gone now you’d have to wonder what sort of prenup he made her sign to ensure she didn’t end up owning the magazine.

Considering those features, it’s perhaps not surprising that she dated Hef; she was the perfect example of his type — his first wife was sort of a plain-jane brunette with 50’s era glasses though.

Sondra Theodore represented the late 70’s era of Playboy and was a true natural beauty, one of the final ones before breast implants and bad perms became the norm — although Playboy did avoid that trend for the longest time.It was after she had an affair that he thought about branching out sexually, and boy did he. While they would later divorce, it perhaps should be lauded for how long it lasted: nine years together and two sons.One of those sons now runs the magazine and was responsible for temporarily removing nudity. After that, she became Playmate of the Month in April of 2000 and Playmate of the Year in 2001.Perhaps that’s what made her bolt in the first place.Playmate of the Month back in 2002, Tina Marie Jordan does remind you a bit of the 90’s super-fake-boobs and bleached blonde look that was synonymous with Playboy at the time.

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She only starring in pictorials for the magazine after they started dating.

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