A Comprehensive History of Demi Moore's Many Loves

Being friends with an ex may not be easy, but Demi Moore recently proved that it is, in fact, possible. The actress participated in Bruce Willis's Comedy Central roast last month, and in addition to delivering some pretty intense burns about the actor's career, she also called Bruce one of her "top three husbands." So, who else has Demi been married to? From actors to musicians to a martial arts instructor, take a look at Demi's past romances ahead.

01
Freddy Moore
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Freddy Moore

Demi's first marriage was to the rock musician from 1980 to 1985, and from the sound of it, their relationship didn't end on good terms. In an interview with Australia's NW magazine in February, Freddy opened up about their past marriage and revealed that he and Demi began seeing each other in 1979 while she was living with her then-boyfriend Tom. "I fell in love with her and as soon as she had me hooked, she dumped Tom and insisted I divorce my wife," Tom said. "I was so infatuated, I did it."

However, the sparks eventually went away. "She changed from being sweet and sexy to mean and angry, flying off the handle at anything," Freddy claimed. "She flirted with lots of guys because they gave her the flattery and attentions she craved." Despite the fact that Freddy and Demi ended their relationship, the actress still kept his last name (Demi's real name is Demetria Gene Guynes).

02
Emilio Estevez
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Emilio Estevez

After meeting on the set of 1985's St. Elmo's Fire, Demi began dating Emilio. The two dated on and off for about two years and even got engaged, though they never made it down the aisle.

04
Brad Pitt
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Brad Pitt

The actress reportedly had a short fling with Brad in 1998.

05
Bruce Willis
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Bruce Willis

Demi and Bruce were married for almost 12 years before they split in 2000. They remained friends after their separation, and have three daughters together, Rumer, Scout, and Tallulah.

06
Oliver Whitcomb
Getty | Diane L. Cohen

Oliver Whitcomb

Following her split from Bruce, Demi struck up a romance with the martial arts instructor, who is seven years younger than her. They dated for almost three years before parting ways.

07
Ashton Kutcher
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Ashton Kutcher

Demi then moved on with Ashton in 2003 after meeting through mutual friends. Demi was married to Ashton from 2005 to 2013. At the time of their separation in 2011, Demi released a statement, alluding to their troubles. "It is with great sadness and a heavy heart that I have decided to end my six-year marriage to Ashton," Demi stated. "As a woman, a mother, and a wife, there are certain values and vows that I hold sacred, and it is in this spirit that I have chosen to move forward with my life. This is a trying time for me and my family, and so I would ask for the same compassion and privacy that you would give to anyone going through a similar situation."

Ashton also addressed the breakup on Twitter, writing, "Marriage is one of the most difficult things in the world and unfortunately sometimes they fail." Their divorce was finalized two years later.

08
Martin Henderson
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Martin Henderson

Before Demi and Ashton's divorce was even finalized, she began dating the New Zealand-born actor in 2012. Their relationship only lasted less than a year.

09
Vito Schnabel
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Vito Schnabel

10
Harry Morton
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Harry Morton

A month later, Demi struck up a romance with another younger man. Harry, who is 19 years younger than Demi, dated the actress for a few months before the pair called it quits in May 2013. "You will occasionally see them together as friends, but they have stopped seeing each other romantically," a source told E! News at the time.

11
Sean Friday
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Sean Friday

In 2014, Demi rang in the New Year with a new romance. After they were spotted on a tropical vacation in Tulum, Mexico in January 2014, People reported that Demi and the drummer had been "hanging out together for months." Demi and Sean dated for a little over a year, though it's unclear what went wrong.