15 Celeb Couples With The Biggest Age Gap

They say that love is blind and that Cupid’s arrow is most likely to hit you hardest when you least expect it. It is rarely convenient, but often worth it. When a couple falls in love, no one else in the world matters, because they have found their soul mate. A pairing that feels perfectly natural may not necessarily meet societal expectations of ideal coupling, but that doesn't mean it won't work out for those involved.

There's a mathematical formula some people consider as a fairly accurate guideline in order to determine whether or not a significant age gap is going to be insurmountable for a couple. The formula is half the oldest person’s age, plus seven. But does a mathematical formula created by those with the purpose of putting societal constraints on people following their hearts really have a place within the world or modern romance? Especially since May/December romances have been around for almost as long as there have been calendars. Some of the most famous romance movies involve big age differences, think Harold and Maude, The Graduate, or How Stella Got Her Groove Back.

While there may be some debate and whispers about whom is dating who, what does it matter in the great scheme of things? Most of these 15 couples would smash any mathematical age related formulas, yet for the most part have managed long term relationships for a considerable length of time despite a hefty age difference. Wine and cheese get better with age. Why not lovers? Let's count down 15 famous couples with big age gaps, from a whisper worthy 15 years difference to a shocking 60.

15 Ashton Kutcher & Demi Moore


Ashton and Demi would “pass” the age math equation if they hooked up today, with a 15 year age gap, but when they met and began dating in 2003, Moore was 41 and Kutcher was 25. The two were married in 2005, and Ashton became a part of the family, alongside Demi Moore and Bruce Willis’s three daughters, Rumer, Scout and Tallulah. Unfortunately, in 2011 the couple split, and their divorce was finalized in 2013. Rumer Willis says she and Ashton (her previous stepdad) have tried to stay in touch, telling Access Hollywood, “It’s nice as I’ve gotten older, I realized the other day that he was a year younger than me [now] when he and my mom started going out, so that would be like me meeting someone who already had three teenage kids and kind of going into that whole situation was crazy.” Rumer then joked that a family reunion probably isn’t in the cards but teased, “It would be the best reality TV special ever.”

14 Ellen DeGeneres & Portia De Rossi


Ellen and Portia met through mutual friends in 2001, and it wasn’t love at first sight. A few years later, in 2004, Portia ran into Ellen at a photo shoot and the second time was a charm! The pair officially started dating in December 2004. In 2008, when the California Supreme Court overthrew the ban on same sex marriage the duo exchanged vows that same August, to a very intimate crowd of 19 friends and family members. The two do not have plans to have children, and enjoy each other’s company along with renovations and remodelling homes. An insider told People Magazine, “They both love to celebrate special occasions and holidays, and their wedding anniversary is no different. They usually celebrate with a big party and invite a lot of friends,” the insider says. “They really are a lovely couple. They enjoy being married, and it shows.” The couple have a 15 year age difference; Ellen is 58 years old, while Portia is 43 years old.

13 Charlize Theron & Sean Penn


Sometimes a big age gap doesn’t work out, despite the duo seeming like a great pair. Sean Penn and Charlize Theron have a 15 year age gap between them, but were seen happily attending red carpet events arm in arm for over a year and a half. The two were even engaged. They began dating in 2013, after their decades of friendship blossomed into romance, and at one point Penn filed to adopt Charlize’s son. Following their break-up, a source close to Theron said, “Charlize was seeing that it was just too intense for her and she needed a breather. She still loves him and respects him to the fullest but she just needed to get out of his intense atmosphere. She is still very young at heart and he plays things by the book.” The two have managed to keep the breakup amicable, and have remained on very good terms.

12 Mary-Kate Olsen & Olivier Sarkozy


While people who grew up in the 1980s may always see Mary-Kate Olsen as a perpetual toddler exclaiming, “You Got it Dude!” Mary-Kate is 29, and a bonafide adult, with a husband who is 45 years old, and 17 years her senior. Olivier Sarkozy is a banker and is half-brother of the former President of France, Nicolas Sarkozy. Their intimate wedding reception hosted only 50 guests, and favours included bowls of cigarettes, so guests could smoke the night away. The pair dated for three years before tying the knot, and Olivier proposed to Mary-Kate during a romantic vacation in Jamaica. Her engagement ring was a four-carat vintage Cartier ring. Mary-Kate didn’t accept Olivier’s first offer though. T he Jamaica engagement was reported to be the second time the banker got down on one knee for the actor, turned fashion mogul, but still best known as Full House’s Michelle Tanner.

11 Leonardo DiCaprio & Nina Agdal


It’s no secret that the Oscar Winning DiCaprio has his choice of leading ladies everywhere. Recently the environmental activist actor began dating Sports Illustrated model Nina Agdal, who is 17 years younger than him. The dapper DiCaprio is quite taken with young Nina, and was spotted at a restaurant in Soho during New York Fashion week. A witness said, “He and Nina were really cute, lots of women were around him, but he was only paying attention to her.” Sources recently told OK Magazine that it isn’t all romance, and the model is tiring of her beau’s “frat boy friends” (including Lukas Haas and Jonah Hill). The source added that Nina feels she’s just being seen as a dumb model and, “She’ll try to start an interesting conversation when they’re around, but with the wolf pack it’s all sports talk and dumb jokes.” Time will only tell if this becomes a deal breaker for the 24 year old and 41 year old DiCaprio.

10 Jason Statham & Rosie Huntington


9 Annette Bening & Warren Beatty


They met on the set of the film Bugsy in 1991. At the time he was 54 and she was a spry 33. The 21 year age gap is the bare minimum for the age equation, and the two have been together for over 25 years now. Warren Beatty was once a legendary womanizer, having once said how he couldn’t sleep at night unless he’d had sex, having bedded nearly an estimated 13,000 women. He had been linked to Joan Collins, Madonna and Carly Simon (who it’s believed had written the song “You’re So Vain” about Beatty). The two had lunch before they began work together and Beatty apparently called the Bugsy director later to declare his love for Bening, and that he was going to marry her. The couple married in 1992 and have four children together. Although Beatty had previously joked that those with a wife of 40 should be able to make a trade for two twenties, much like currency, the pair appear to be keeping it together.

8 Harrison Ford & Calista Flockhart


They met at the Golden Globe Awards nearly 15 years ago, but we know that Calista shot first in pursuing her Han Solo. She intentionally spilled her drink on Ford in hopes of securing some face time with the star, who is 22 years older than her. The two were dating for two years before Harrison Ford officially divorced his screenwriter ex-wife, Melissa Matheson, although the former couple had been separated for over a year before he met Flockhart. Harrison has said of his relationship, “I was 60 when I fell in love with Calista, 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."

The pair were eventually wed at the New Mexico Governor’s mansion after eight years together as a couple. It was an intimate affair with a very select guest list, even Ford’s four grown children didn’t make the guest list. His son Ben joked with People magazine, “Those crazy kids went off and eloped! I’m so happy for them.” Today the couple can be seen out and about at sporting events, still enjoying each other’s company.

7 Donald Trump & Melania Trump


This list wouldn’t be complete without a mention of the 24 year age difference between presidential candidate Donald Trump and his wife Melania. Melania is a jewelry and watch designer, and former model, and Trump’s third wife. Melania met “The Donald” at a party in New York City during fashion week in 1998. Although Melania was reluctant to give Donald her phone number initially, the two began dating for a short period of time before Melania broke it off. The two reconciled a few months later, were engaged in 2004, and married in Palm Beach Florida in 2005. Hillary Clinton and Bill Clinton were guests at the couple’s wedding. In 2006 Melania gave birth to their son Barron William Trump. Barron reportedly has his own floor in the Trumps’ apartment in Trump Tower, Manhattan, enjoys wearing a suit, plays golf with his father, and his mother’s nickname for him is “Mini-Donald.”

6 Michael Douglas & Catherine Zeta-Jones


They’ve had their series of ups and downs as a couple, because who hasn’t? However, through it all they’ve maintained a strong relationship together. They have worked through Douglas’s 2010 diagnosis with stage four mouth cancer, and Zeta-Jones facing her diagnosis of bipolar disorder. The pair met at a film festival in 1998, and were married in 2000. Today Douglas is 72 and Zeta-Jones is 47, with a 25 year age difference between them. They have two children, Dylan (16), and Carys (13). In speaking with the Daily Mirror about his wife, and their marriage, the actor said, “Catherine was extraordinary. She really took hold of the issue in a way, with due respect, that is not always true of the Brits.” He added, “In the end we were able to see the big picture and move on. Now, we’re closer than ever.” Michael has also said that surviving cancer has helped him learn to live in the moment.

5 Holland Taylor & Sarah Paulson

via abcnews.go

Sarah Paulson is best known for her role on the hit series, American Horror Story, however more recently she’s been known for her May-December Romance to Holland Taylor. Paulson is 41 years old, and she is dating Holland Taylor, known for her work on The L Word and The Truman Show. The two actors met at a dinner party over a decade ago, but Paulson was in another relationship at the time. In speaking about her choices and relationship Paulson has said, “If my life choices had to be predicated based on what was expected of me from a community on either side, that's going to make me feel really straitjacketed, and I don't want to feel that," Paulson told the newspaper of her partner, 32 years her senior, "What I can say absolutely is that I am in love, and that person happens to be Holland Taylor."

4 Woody Allen & Soon Yi Previn


This big age difference has a definite ick factor to it that made headlines, since after all he was pretty much her stepfather. Soon Yi Previn was the daughter of Woody’s girlfriend Mia Farrow (Soon Yi was adopted by Farrow). Farrow decided to separate from Allen in 1992 when she discovered naked photos of her daughter that had been taken by the director. There are 35 years between the two, who began a relationship and were married in 1997. They adopted two daughters, one in 1999, and one in 2000. The two remain a couple today, celebrating nearly 25 years together. Despite the controversy, and allegations from another adopted daughter surrounding sexual assault, Woody Allen has still enjoyed a successful career. When Allen was asked how his relationship with Soon Yi has changed him by The Hollywood Reporter, he said, “Changed me? I don’t know if you could say she changed me... I might be the same person I was when I was 20.”

3 Steven Tyler & Aimee Ann Preston


There is nothing new about workplace romances, even if the business is music, fame, and fortune. Trailblazer rocker Steven Tyler, lead singer of Aerosmith, found romance with his assistant, Aimee Ann Preston, who is 39 years younger than him. She is 28, and he is 68 (Tyler’s daughter Liv is 39, and daughter Mia is 37 years old). The two have kept a fairly low profile, but were seen holding hands at the Elton John AIDS Foundation Viewing Party in February 2016. This was their official “public debut” as a couple. They were first suspected of being a couple in 2014, when they were seen together on a vacation in Maui. Aimee was previously an assistant in the Trump Organization (yeah that Trump) and began working for Tyler in 2012. The couple moved in together in March 2016. A source close to Tyler has said, “People are always wondering and now it’s kind of finally out in the open. I think at some point, because she is always with him and does live with him, it’s like ‘OK, it’s more than just a personal assistant.’ They’re out together all the time. She doesn’t leave his side.”

2 Mick Jagger & Melanie Hamrick


1 Hugh Hefner & Crystal Harris


Legendary Playboy Hugh Hefner has been slaying the ladies for decades and released the first ever issue of Playboy magazine in 1953 with cover model Marilyn Monroe. The world famous ladies’ man has been married three times (so far) in his 90 plus years. Most recently he got hitched to model Crystal Harris who is 60 years younger than him. He and Harris started dating in 2008, were engaged in 2011, and have been married to each other since 2012, holding the ceremony at the infamous Playboy Mansion. Hefner has four children (all from previous relationships) with his youngest child born in 1991, and five years younger than Step-Mother Crystal.

Sources: EOnline, OK Magazine,, ETOnline, HuffingtonPost

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15 Celeb Couples With The Biggest Age Gap