Private Investigator Exposes Casey Kasem’s Widow
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Private Investigator Exposes Casey Kasem’s Widow

May-December relationships can get tricky when there are kids involved, and no one found that out better than the late Casey Kasem, who may never be able to rest in peace, because his family is still viciously attacking each other in the media. And neither side seems willing to back down.

Clint Eastwood’s Newest Sugar Baby
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Clint Eastwood’s Newest Sugar Baby

He may be 84 years old, but Clint Eastwood still obviously has a way with the ladies, especially the younger ones. The actor has reportedly been dating Christina Sandera, who works as a hostess at his ranch hotel in California. The couple was recently photographed leaving a grocery store together and although Sandera’s age isn’t known, it’s clear in the pictures that she’s much, much younger than him.

Marc Anthony Talks Being “Ugly” and Dating Hot Younger Women
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Marc Anthony Talks Being “Ugly” and Dating Hot Younger Women

Let’s be honest, Marc Anthony isn’t the most attractive older man. And yet, the 45-year-old singer has been able to score with some very beautiful ladies, like his ex-wives Jennifer Lopez and Dayanara Torres. Not to mention his many May-December relationships with younger women, including Topshop heiress Chloe Green, 22, and his most recent May-December romance with 26-year-old model Shannon De Lima. How does Marc Anthony do it?

Rosamund Pike, Expecting Second Baby with Her Man, Robie Uniacke
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Rosamund Pike, Expecting Second Baby with Her Man, Robie Uniacke

British actress Rosamund Pike, 35, whom you may recognize as the Bond girl from Die Another Day, is not only dating a much older man, but she’s about to have his second baby. The other half of Pike’s celebrity May-December relationship is 53-year-old businessman Robie Uniacke. The celebrity couple already has one two-year-old son together.

Katharine McPhee Files for Divorce After Cheating on Her Husband
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Katharine McPhee Files for Divorce After Cheating on Her Husband

After she was caught having an affair with her Smash director, Michael Morris, actress Katharine McPhee, 30, tried to save her marriage to Nick Cokas, who’s 19 years older. The celebrity couple quietly separated after the affair scandal surfaced, but it seemed like their May-December relationship was back on track when insiders revealed that they were spending almost all their time together to try and work on their marriage.

Richest Actor in the World with $800 Million
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Richest Actor in the World with $800 Million

There’s no doubt that women are naturally draw to men with money, especially when they’re smart, mature, and really know what it takes to make a relationship work. That’s why so many younger women are dating older men these days. It’s just an added bonus if the older man also happens to be a world-famous celebrity. It was recently revealed that the richest celebrity in hip hop is Sean “P. Diddy” Combs, with an estimated fortune of $700 million.

Casey Kasem’s Younger Wife Ordered to Appear in Court
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Casey Kasem’s Younger Wife Ordered to Appear in Court

The ongoing dispute between Casey Kasem’s kids and his younger wife (who’s their stepmother), Jean Kasem, has gone from a family feud to a full-blown war. Casey Kasem, 82, suffers from advanced Parkinson’s disease, and his kids are claiming that his younger wife, who’s been married to the radio icon for 34 years now, is keeping him locked away from family and friends as he inches closer to his death.

Another Royal Baby on the Way
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Another Royal Baby on the Way

Princess Charlene, 36, has said in the past—on more than one occasion—that she’s ready to have kids with her much older husband, 56-year-old Prince Albert of Monaco. Her wish has now been granted, because the royal couple is officially expecting their first child. The palace of Monaco released an official statement confirming the celebrity couple’s pregnancy news, adding that the baby is expected to arrive at the end of 2014.

Liberty Ross Collects “Guilt Money” in Divorce from Rupert Sander
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Liberty Ross Collects “Guilt Money” in Divorce from Rupert Sander

There’s never a shortage of drama in celebrity May-December relationships, especially when there’s an affair involved. Director Rupert Sanders, 43, will probably never be able to live down his now infamous May-December romance with 24-year-old actress Kristen Stewart, who was supposed to be in a committed relationship with her Twilight co-star Robert Pattinson at the time.

Kenneth “Babyface” Edmonds Weds Longtime Girlfriend
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Kenneth “Babyface” Edmonds Weds Longtime Girlfriend

R&B singer-songwriter and producer Kenneth “Babyface” Edmonds, 55, surprised fans in February 2014 when he revealed in an interview that he and his younger girlfriend, 41-year-old Nicole Pantenburg, were engaged. After the interview, he released a statement confirming that he really was “on the love marriage path” and that he was a “very lucky guy.” Fast forward three months and the celebrity couple is now officially husband and wife.

Paul Walker’s Younger Girlfriend, Still Grieving His Death
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Paul Walker’s Younger Girlfriend, Still Grieving His Death

When Paul Walker died suddenly in a tragic car crash on November 30, 2013, he not only left behind a 15-year-old daughter, but also his girlfriend of seven years, Jasmine Pilchard-Gosnell. The celebrity couple first met when Paul Walker was 33 and Pilchard-Gosnell was only 16. But despite their 17-year age difference, they were very happy together and even shared a home in L.A.

Tori Spelling Says It’s Her Fault Her Husband Cheated
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Tori Spelling Says It’s Her Fault Her Husband Cheated

It was recently revealed that Tori Spelling and Dean McDermott would be making the most of his affair with a younger woman, by airing their marriage troubles on national television for the world to see. The Lifetime network has just released a sneak-peek of the celebrity couple’s new docu-series, True Tori¸ and it doesn’t look like they’re planning to hold anything back.

Jude Law Makes a Fool of Himself Trying to Seduce a Playboy Model
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Jude Law Makes a Fool of Himself Trying to Seduce a Playboy Model

Jude Law clearly has a thing for younger women, and it seems to always cause problems for him. While engaged to actress Sienna Miller back in 2005, he admitted to having an affair with the celebrity couple’s young nanny. Then in 2008, he briefly dated model Samantha Burke, who was 12 years younger, and wound up getting her pregnant—the younger woman gave birth to a daughter, Jude Law’s fourth child, in September 2009.