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.”
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
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.”
Donald and Melania Trump
Doug Hutchison and Courtney Stodden
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
“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.”