Have you ever witnessed a rollercoaster that makes the stomach plummet and the heart soar, all in the same breath? Well, Charlie Sheen’s love life mirrors exactly that—a thrilling, unpredictable adventure with twists & turns that defy the odds. Given up on love or simply safeguarding his heart from another strikeout, the Platoon actor, 58, has once made headlines, refusing to walk down the aisle with Natalie Kenly, his former partner who loved him dearly.
Back in 2011, he shared the spotlight with his goddesses, among them model-graphic designer Natalie Kenly, who claimed to have fallen for Sheen’s intellectual charm. Despite the stars aligning in their cosmic cradle, the actor, with the frankness of a baseball player batting zero for three in the game of matrimony, decided not to swing, dodging what he jokingly dubbed a “golden sombrero”.
Love Unreturned: The Story Behind Charlie Sheen-Natalie Kenly’s Broken Dreams
Charlie Sheen, the man with more curves in his life than a winding road, is known for his unconventional approach to relationships. The actor, known for his rollercoaster of a life, has never been one to shy away from controversy.
In 2011, he introduced the world to his “goddesses”, Natalie Kenly and Bree Olson. These two women, who he claimed completed his heart, were a far cry from the typical Hollywood starlet. Sheen said, comparing his romantic failures to a sports statistic (ABC News):
I tried marriage. I’m 0 for 3 with the marriage thing. So, being a ballplayer — I believe in numbers. I’m not going 0 for 4. I’m not wearing a golden sombrero.
Despite the love and affection the Two and a Half Men star received from these women, he made it clear that marriage was not in his cards. Having already been through the matrimonial ringer three times at the time, Sheen joked that he was not going to strike out with a fourth attempt at holy matrimony. “I’m not wearing a golden sombrero”, he quipped, making light of his failed marriages.
His light-hearted approach to marriage and relationships was further demonstrated when he flippantly mentioned starting a polygamous marriage, jokingly referring to himself as the “wedge”.
The Women of Charlie Sheen: A Deep Dive into His Love Life Misadventures
When Jon Bon Jovi crooned You Give Love a Bad Name, he could’ve easily been singing about Charlie Sheen. Being the toast of Tinseltown with his heartthrob looks and charismatic roles, his career has hit more than a few rough patches.
In the late ‘80s and early ‘90s, a young and dashing Sheen was engaged to actress Kelly Preston, but the story of their split took on a life of its own. Per Newsweek, rumors swirled that Sheen had shot Preston, ending their engagement with a bang. While this outlandish tale sounds like it could be ripped from a tabloid headline, it’s just another example of the outlandish legends that have followed Sheen.
Sheen’s first marriage was to model Donna Peele in 1995. At the time, the former gushed about Peele, saying, “Just when I thought I was the luckiest guy alive, I just got a lot luckier” (via The Spokesman-Review). He hailed her as his soulmate and best friend.
The drama continued in 2018 when Heidi Fleiss revealed juicy details about Sheen’s extravagant habits. According to The Hollywood Reporter, Fleiss claimed that Sheen had grossly underreported his spending on her services, claiming he had splurged between $300,000 and $400,000, while Sheen had only admitted to $60,000.
By the late ‘90s, Sheen’s romantic life took another nosedive with actress Brittany Ashland. Their relationship was anything but smooth sailing. Ashland accused Sheen of domestic violence, leading to charges of misdemeanor battery in 1997 (via Los Angeles Times).
In Sheen’s world, love may have a bad name, but it’s the entire saga that’s the real page-turner. So, whether you agree with his choices or not, we can’t deny that the actor will always march to the beat of his own drum, even if it means forgoing the traditional path to love and marriage!
