Clint Eastwood and Dina Ruiz- Eastwood
Age difference: 35 years
In 1993, Dina Ruiz interviewed Clint Eastwood for a local news show in Flagstaff, Arizona. At 63, he was 35 years her senior, but had an undeniably youthful energy, and each made an impression on the other. The two crossed paths over the next few years, and in 1996, they were married. Last year, the couple took their relationship more public with the debut of Mrs. Eastwood & Company, an E! reality show featuring Dina and their daughter, Morgan, as well as Eastwood's daughter with actress Frances Fisher, Francesca. "She's crazy, wild, and hilarious," Francesca told The Daily Beast about Dina in 2012. "She's sort of the opposite of my dad, who’s very calm, so they really balance each other out well."

Bruce Willis and Emma Heming
Age difference: 23 years

After watching his ex-wife, Demi Moore, marry a younger man, and after dating a string of younger women, Bruce Willis finally decided to settle down for a second time with model Emma Heming—23 years his junior. (Moore and her then-husband, Ashton Kutcher, even attended the 2009 wedding in Turks and Caicos.) "I spent the last 10 years single and, for the most part, unhappy. In a dark place. I never thought that being with someone else was the answer," Willis admitted soon after getting married. "Then I started hanging around Emma, and on a day-to-day basis my life became much happier." And last year, the actor added yet another much younger woman to his life—Heming gave birth to Willis' fourth daughter, Mabel.
 Michael Douglas and Catherine Zeta-Jones
Age difference: 25 years

With some couples, a large age difference can have little meaning. But for Michael Douglas and Catherine Zeta-Jones it almost seems like fate. The two are 25 years apart—to the day. (Both born on September 25.) Now 68 and 43, the pair have been married since 2000 and have two children together. "We didn't care about the age gap from the beginning on," she said ten years into their marriage. "We relied more on our emotions and feelings. It was like that and it should always be like that."
 

Dick Van Dyke and Arlene Silver  
Age difference: 46 years

Plenty of men claim to be serial monogamists, but Dick Van Dyke has the history to prove it. He was married to his first wife for 36 years and the couple had four children together before divorcing. He then lived with girlfriend Michelle Triola for more than 30 years, until her death in 2009. And three years later, the 86-year-old Mary Poppins star said, "I do" for a second time when he married 40-year-old makeup artist Arlene Silver. The two were married in a low-key ceremony—in which the bride wore a fuchsia dress from Anthropologie—on Leap Day 2012 and Van Dyke clearly looked before he leaped. "I'm not a loner," he admitted at the time. "I have to have a life partner. I found the perfect one."

 Donald and Melania Trump
Age difference: 24 years


When 58-year-old Donald Trump married his third wife, 35-year-old model Melania Knauss, in 2005, he made one of his bold predictions: "I think it will be very successful," Trump declared. Eight years and one son later, the real estate mogul certainly sounds thankful for his good marital fortune. "As a younger person, you're running through life, and you don't think there will ever be an end to the whole thing," he told Oprah. "I think when you get older, and you have some special people around you that are very young, I really believe you appreciate it more." And in a perfect bookend, Trump's first wife took a chance on May-December love herself in 2008—59-year-old Ivana married Rossano Rubicondi, who was 24 years her junior. Alas, the marriage ended after eight months.

 Doug Hutchison and Courtney Stodden
Age difference: 35 years


"This is my child," 52-year-old Doug Hutchison said of his 18-year-old bride, Courtney Stodden, during an episode of VH1's Couples Therapy. "I'm raising my wife." Even by Hollywood standards the age difference between Green Mile actor and the teen seemed to be shocking, but Hutchison explained it away. "I always joke with Courtney that one of the reasons we worked,” he told Good Morning America when they married in 2011, "is 'cause she's 16 going on 36, and I'm 51 going on 21."

Harrison Ford and Calista Flockhart
Age difference: 22 years

Seven years into his relationship with Calista Flockhart, the man who played Han Solo decided he didn’t want to be solo anymore—on Valentine’s Day 2009, Harrison Ford proposed to the Ally McBeal star (who is 22 years his junior) and they were married the next year. "I was 60 when I fell in love with Calista," he told Hello! magazine of their romance. "What surprised me most was that I was still capable of establishing a long-lasting relationship, making a serious commitment. With my children, in my private life or my work, I try to learn from my mistakes and evolve."

 Kelsey Grammer and Kayte Walsh
Age difference: 25 years


When 56-year-old Kelsey Grammer's marriage to his third wife, Camille, ended abruptly in 2010, the scandal was compounded by the emergence of the other woman who would soon become Wife No. 4—29-year-old flight attendant Kayte Walsh. Two years after the two were married, Walsh gave birth to Grammer's fifth child, Faith, who is younger than his first grandchild.


Woody Allen and Soon-Yi Previn
Age difference: 35 years

"If somebody told me when I was younger, 'You're going to wind up married to a girl 35 years younger than you and a Korean, not in show business, not having any real interest in show business,' I would have said, 'You're completely crazy,'" Woody Allen admitted to Vanity Fair in 2005.  "Because all the women that I went out with were basically my age. Two years younger. Ten years was the maximum. Now, here, it just works like magic." But Allen’s relationship with Soon-Yi Previn came with a heavy price. In 1992, the director's longtime companion, Mia Farrow, discovered nude Polaroids he had taken of Previn, Farrow's adopted daughter. More than 20 years later, however, Allen has made peace with their controversial beginning because of the relationship's happy ending: "It's got a more paternal feeling to it," he said. "I love to do things to make her happy. She loves to do things to make me happy. It just works out great. It was just completely fortuitous. One of the truly lucky things that happened to me in my life."

 
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