By | Published on Sep 07, 2017

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5 Strong Women Who Were Once Sugar Babies

Sep 07, 2017 Eryn Sophie

Not all Sugar Babies are bred equal.

Sugar Babies have a highly stigmatized reputation. The general and stereotypical opinion reckons that the only way they managed to be successful is due to the financial support of their Sugar Daddies however, that is not entirely true.

And in some cases, Sugar Babies have made it on their own merit. They just chose to date powerful, wealthy and older men because let’s face it, who would want to date broke-ass, lazy and boring boys when there is a choice.

Here are 5 strong women who were once Sugar Babies and they aren’t ashamed to admit it. (You do you, girl).


  1. Lisa Ling

She is an American journalist, television presenter and author and is currently the host of This is Life with Lisa Ling on CNN. Her resume boasts of ABC’s The View, National Geographic Explorer, Channel One News and special correspondent for The Oprah Winfrey Show.

In 2014, she publically outed herself as a Sugar Baby. Even though she is a diehard feminist and fiercely independent, she admitted she was in a relationship with a man much older than her named Tom when she was in her twenties.

In a CNN transcript, she stated “Now there’s nothing wrong with being in a relationship in which one person financially supports the other. We all contribute to our relationships in different ways and in no way should any contribution be trivialized.

She is now married with child to a man who is successful in his own right.

  1. Holly Madison

Former Playboy Playmate Holly Madison who became famous from the E! Reality TV show Girls Next Door, wrote a tell-all book entitled Down The Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny in 2015, was once the apple of Hugh Hefner’s eye.

In her book, she described that she was ‘feeling shitty’ about her first encounter with Hef but it was her who asked to be invited to the Mansion. She had lost the lease to her apartment and was at odds with making ends meet and she saw a way out and took it.

Comments from her book were quite supportive and rational. Most acknowledged that both parties were adults and each made their choices as adults to get what they need from each other to survive and fulfil their own personal wants.

  1. Dina Eastwood

Dina was just 27 when she met Clint Eastwood who was aged 62 at an interview where she was the one conducting it in 1992. She married him in 1996 and retired from her news anchor position in 1997 after her daughter was born.

They divorced in 2014 and throughout their marriage, she’s got a few work here and there with the most notably position of Board of Trustee for The California Museum for History, Women and the Arts, like most socialites. She also manages an acapella group called the Overtones.

She’s currently happily remarried to basketball coach, Scott Fisher while Clint Eastwood is busy lavishing a new Sugar Baby who was married to Scott Fisher and is 42 years old while Clint is 83. Yeah, it’s a rather complicated modern relationship.

  1. Heather Harlan

Before you go, who? Heather Harlan is the widow to legendary actor, Tony Randall, best known for his role as Felix Unger in the TV series The Odd Couple who died in 2004 at the age of 84. She was 36 at the time of his death.

When Heather met Tony, she was an intern in one of his theatrical programs and their wedding was officiated by Rudy Giuliani in 1995. She was a nubile 25-year old blonde and he was an aging but sprightly 75. Based on every aspect, they were truly in love.

Once, she read a blog that said something like, “[Heather Randall] inherited his fortune when he died — which was her aim.” “That kinda stung,” she stated. Everyone had an opinion. “Did his friends think I was a gold digger at first? Well, I remember one or two women telling him he was an old fool…and I’m sure people said and continue to say things behind my back,” Heather laughs. “But I don’t hear most of it.”

She’s been single since he’s passed away and keeps herself busy by managing the estate he left behind.

  1. Melania Trump

Born in Slovenia in 1970, she started her modelling career at 16 and she met the now President of United States at the Kit Kat Club in 1998 at a New York Fashion Week when she was 28.

She held her Sugar Baby position for many years, only getting upgraded to wife in 2005 in a grand wedding in Mar-a-Lago. She wore a USD $200,000 dress specially made by John Galliano of the house of Christian Dior.

Listed as a ‘full-time housewife’, Melania assumed the role of First Lady of the United States of America on January 20th, 2017, the ultimate level-up for a Sugar Baby. Not without controversies as she’s had her Sports Illustrated days’ photos rehashed, but like a true lady, she’s held her head high and proud.