Charlie Sheen is probably one of the most controversial actors in Hollywood history. The man has been on the news more times than anybody can count, and his love life has been a huge part of the media fodder. Amongst his many failed relationships, few people know about his very brief engagement with model and adult film star Scottine Ross.
They met in November 2013, dated until January 2014, got engaged, and called it off later that year. And in typical Charlie Sheen fashion, it didn’t end there. Ross sued Sheen for a whopping $5 million dollars, and they ended up settling for an undisclosed amount. Yikes!
Uma Thurman and Arpad Busson
Uma Thurman hasn’t had much luck in her personal life. When it comes to love, Thurman has been married twice – to Gary Oldman and Ethan Hawke – and both times it ended in divorce. In 2007, she decided to give love another chance and started dating French financier Arpad Busson. By 2008, they were engaged, but called it off shortly after, with Uma returning the 8-carat diamond ring Busson had given her.
But they got back together, and four years later, they had a daughter. However, they couldn’t make the relationship work. In 2014, Thurman ended things for good, saying Busson was too controlling; they went on to have a nasty custody battle for their daughter, which Thurman ultimately won.
Johnny Depp and Jennifer Grey
“Dirty Dancing” star Jennifer Grey skyrocketed to fame after her role in the 1987 hit film. The star was dating Matthew Broderick in 1987 and became engaged shortly after. Unfortunately, a terrible car crash the couple had in Ireland which ended up taking two other peoples’ lives proved to be too much strain for Grey and Broderick, and they finally broke up in 1988.
As it turns out, Grey had started seeing Johnny Depp a few weeks after ending it with Broderick. Depp and Grey, who met through Grey’s agent, got engaged after just two weeks of seeing each other, meaning Grey was engaged to two different men during the same month in 1988. They lasted a year and then broke things off for good.
Jennifer Aniston and Tate Donovan
If you were a fan of “Friends,” you’ll remember the episodes when Rachel becomes smitten with one of her customers – Joshua, played by actor Tate Donovan. But few people know that these two had an actual love story behind the cameras. Before getting cast on “Friends,” Tate Donovan had dated Jennifer Aniston for three years and even popped the question in 1998.
They were engaged for a few months before calling it off – apparently, the media pressure was too much for Donovan. So, it was incredibly awkward when Donovan got cast in five episodes of “Friends” and had to work next to his ex-fiancé every day. Luckily, they both moved on; Anniston went on to marry twice and then get divorced, and Donovan married once but also ended in divorce.
Nicollette Sheridan and Michael Bolton
The talented blonde bombshell Nicolette Sheridan is most known for her roles in “Desperate Housewives” and “Dynasty.” But she’s been in the Hollywood scene since the 90s, and so was her almost-husband Michael Bolton. The famous singer-songwriter and the actress dated from 1992 until 1995, when they broke things off.
Then, in 2005, they rekindled the relationship and even got engaged. People thought things were finally going to work out between them, but alas, in 2008, they decided to go their separate ways. Bolton never married, and Sheridan married actor Aaron Phypers in 2015, but got divorced three years later.