Demi Moore is 57-years-old. She has, since her split from Bruce Willis around 20 years ago, gone through a fair number of men, most of them considerably young than she is. The relationships never last. But she never seems to learn, simply moving on to the next boy toy.
The list doesn't include all the loves she has taken up with, but it is a pretty representative sampling of the (mostly) younger men she has dated, had encounters with, or whatever.
At 57 and now in lockdown with her family, Moore's love life seems to be on hold. Here's hoping she finds true love with the right man of the right age. Here are 15 guys Demi Moore has had in her life since her divorce from Bruce Willis.
And no, Willis does not approve of the boy toy thing. He thinks it sets a bad example for their three daughters.
15 Brad Pitt - 1 Year Younger
Back in 1998 when Moore's marriage to Bruce Willis was in tatters, rumor had it that Demi and Brad Pitt "bonded" over a sensual yoga class. It was just a rumor that made the rounds, but it has had staying power. Seems the two have taken up the sensual yoga thing again, in the wake of Brad's split from Angelina Jolie.
14 Oliver Whitcomb - 8 Years Younger
Oliver Whitcomb is only 8 years younger than Demi Moore! So, not too bad. He is a tall and lanky martial arts instructor that Moore dated off can on between 1999 and 2003. Wonder if he taught her some self-defense moves? Whitcomb it the owner and chief instructor of an outfit call Sawtooth Martial Arts.
13 Anthony Kiedis - Same Age
Anthony Kiedis is famous for dating Demi Moore in 2002, but much more so for being the lead vocalist for the legendary rock band Red Hot Chili Peppers. And, miracles of miracles, he and Demi are around the same age. Like many aging rockers, he has sometimes tended to go for much younger women, much in the same way as Demi likes boy toys. The relationship was brief, but (we hear) fun-filled.
12 Tobey Maguire - 13 Years Younger
The Spider-Man actor and Demi dated in 2002. Some even thought it was quite serious, with talk of wedding bells making the rounds. Then, all of a sudden, he dumped her for a younger woman he was seen making out with in the back of a car. Demi was, of course, devastated. She had really hoped Tobey would be THE one.
11 Colin Farrell - 14 Years Younger
The Irish actor seems to appeal to women. He is off the wall, outspoken, unpredictable, and getting onto a bad boy. Demi hooked up with him early in 2003. And by all accounts, it was a brief (but wild) ride. Farrell, who is 14 years younger than Demi, moved on pretty quickly. You would think Demi would get the message. But no, it gets worse.
10 Ashton Kutcher - 16 Years Younger
Ashton Kutcher and Demi Moore married in 2005. It came as something of a shock in entertainment circles. Outwardly, they seemed happy, but Moore has now revealed that on a couple of occasions Kutcher talked her into doing the threesome thing in between the sheets. He later used it as an excuse for the cheating that brought a screeching halt to their marriage. The couple was divorced in 2013 following his romp in a hot tub.
9 Vito Schnabel - 24 Years Younger
You may remember Schnabel from his three-year affair with cougar Heidi Klum. But before Klum, there was Demi. The 24 year age gap was bad enough, but Demi took to showing up at parties Schnabel was attending and creating scenes. Schnabel, an art dealer, was embarrassed, and fearing notoriety ended the brief affair in December of 2012.
8 Martin Henderson - 12 Years Younger
2012 was a busy year for Demi Moore. Maybe it had something to do with her turning 50. Moore had what is euphemistically called an "encounter" with New Zealand actor Martin Henderson over the summer of 2012. From the beginning, it had the look and feel of a hit and run kind of thing. And it was. Henderson is perhaps best known for his role in Grey's Anatomy.
7 Thomas Jane - 7 Years Younger
It was 2012's (pretty bad) movie LOL that seems to have brought them together. In it, Hung star hunky Thomas Jane and Demi Moore played the divorced mother and father of Lola, played by Miley Cyrus. The movie was pretty forgettable and the fling or encounter or whatever it was that took place between Jane and Moore came and went pretty quickly.
6 Alex Rodriguez - 13 Years Younger
Demi Moore and A Rod's names were very briefly linked in 2012. Alex Rodriguez has been one busy man about town, with romantic links to the likes of Cameron Diaz, Kate Hudson, Madonna, and (of course now) Jennifer Lopez. Demi and Alex Rodriguez were seen out on a dinner date or two in 2012.
5 Harry Morton - 19 Years Younger
Demi and the restaurateur dated for a bit in 2013. Said one observer of one of their dinner dates: “Demi was very giddy during her date with Harry. She was really into him and seemed to very much enjoy his company.” The affair was short-lived. Tragically, the 38-year-old died of a heart attack in 2019.
4 Peter Morton - 15 Years Older!
Harry Morton and Demi parted ways amicably in 2013, but not before he had introduced her to his 60-something father Peter. Peter Morton, the founder of the Hard Rock Cafe chain is said to be charming and charismatic. It was a great friendly dating relationship between the two and represented the first time Demi had been with anyone older than she is since Bruce Willis!
3 Will Hanigan- 20 Years Younger
This guy is an Aussie yoga teacher who moved to Los Angeles where he hooked up with Demi in 2013. What to say about Will? Well, he had a pearl inserted into his "family jewels" when he was a youngster. He claims it enhances his performance between the sheets. He gushed about what an amazing woman Demi was. Surprise, surprise. It didn't last long.
2 Sean Friday - 24 Years Younger
They were seen putting on a PDA show on a beach in Mexico in the summer of 2014. Sean, the drummer of Dead Sara who is 24 years younger than Demi, seemed happy enough! They dated for a few months and then, surprise, surprise, just like Ashton Kutcher, he dumped her for a younger woman. There's a pattern here, Demi.
1 Nick Jonas - 30 Years Younger
In 2018 it was claimed that none other than daughter Rumer Willis had introduced Demi to Nick Jonas at a party. And, reportedly, they clicked. "Meetings" were held at clandestine locations. Demi wanted to keep it hush-hush. Demi, as we all know, has a thing for younger guys and Nick has had some experience with older women. A perfect match.