It’s not unusual for people of different ages to marry. Indeed, relationship experts agree that love can easily blossom even with as many as ten years between partners. But when the age gap stretches to decades, things can easily become a little strained. And it isn’t just prying eyes that can drive a marriage apart when one partner is old enough to be the other’s parent.
Nevertheless, some such relationships can endure. Indeed, Hollywood is full of inter-generational couples. And many of these marriages have stood the test of time – even if time seems to be against them.
20. Catherine Zeta-Jones & Michael Douglas (25 years)
After meeting at the Deauville Film Festival in 1998, Catherine Zeta-Jones and Michael Douglas would eventually wed in 2000. Yet despite an age gap of 25 years, the screen stars, who both appeared in 2000’s Traffic, have remained together bar a brief 2013 split. They now enjoy a seemingly happy marriage with children Carys and Dylan.
19. Mary-Kate Olsen & Olivier Sarkozy (17 years)
Best known as a child star who often appeared alongside twin sister Ashley, Mary-Kate Olsen turned heads when she began dating Olivier Sarkozy. That Olivier is the brother of former French President Nicolas Sarkozy was newsworthy in itself, but the pair’s 17-year age gap also defied conventions. Nevertheless, they have remained an item since their first encounter at a party in 2012 and married three years later.
18. Aaron Taylor-Johnson & Sam Taylor-Johnson (23 years)
But it isn’t just female stars who go for older partners. While working on 2009’s Nowhere Boy, then 19-year-old actor Aaron Johnson began dating his then 42-year-old director Sam Taylor. Though many dismiss the relationship as a fling, the pair subsequently married in 2012 and have gone on to have two children together.
17. Calista Flockhart & Harrison Ford (22 years)
She may only have been 13 when his career-making turn in Star Wars hit the big screen, but Calista Flockhart and Harrison Ford have still forged a lasting relationship together. Following a chance encounter at the 2002 Golden Globes, the former Ally McBeal star began dating Ford, who is 22 years her senior. They eventually tied the knot in 2010.
16. Shania Twain & Robert “Mutt” Lange (17 years)
After starting out as a musical partnership in 1993, Shania Twain and Mutt Lange’s relationship soon turned to a romantic one. In fact, the country sensation took the 17 years senior Lange’s hand in marriage only six months later. However, the union wasn’t to last, and Lange left Twain for one of her closest friends in 2008.
15. Katie Holmes & Tom Cruise (16 years)
One of Hollywood’s most infamous marriages, Katie Holmes and Tom Cruise had a much publicized relationship between 2005 and 2012. The two first met to discuss a role in Mission: Impossible III, allegedly at the behest of senior Scientologists. And their subsequent coupling became the subject of much media speculation. That being said, the pair’s 16-year age gap was far from being the most discussed aspect of their romance.
14. Phoebe Cates & Kevin Kline (16 years)
Following her breakout role in 1982’s Fast Times at Ridgemont High, Phoebe Cates attended an audition for The Big Chill the following year. There she met actor Kevin Kline and, in spite of a 16-year age difference, they began a relationship soon after. Still together after 28 years of marriage, the pair are parents of two children and seem blissfully happy.
13. Julie Chen & Les Moonves (20 years)
Though Les Moonves was 20 years her senior – as well as a married man at the time – CBS anchor Julie Chen still pursued a relationship with her network’s president in the early ’00s. But while their subsequent marriage has gone smoothly, Chen has been accused of using her husband’s status to her advantage. In particular, she has been criticized for her alleged meddling behind the scenes on The Talk, which she co-hosts.
12. Annette Bening & Warren Beatty (21 years)
As one of Hollywood’s most notorious lotharios, Warren Beatty seemed destined for a life of singledom. However, that all changed when he met actress Annette Bening while filming Bugsy in 1990. Despite a 21-year age gap, the two hit it off and their two-decade marriage has yielded four children.
11. Stephanie Seymour & Peter Brant (22 years)
Best known for her modeling work with Victoria’s Secret, Stephanie Seymour met publisher and real estate tycoon Peter Brant in the mid ’90s through a photographer friend. After Brant divorced his then wife, he and Seymour eloped in Paris before beginning an often turbulent marriage. Indeed, the two, aged 22 years apart, experienced a bitter divorce battle before reconciling in 2010.
10. Bo Derek & John Derek (30 years)
Admittedly, dating a much older man is a pretty weird concept in any circumstances. But Bo Derek’s relationship with director John Derek is actually downright creepy. To wit, they met while filming Fantasies in 1973 when John was 46 and the 10 star was only 16. After Bo turned 18 in 1976, the pair wed and remained married until John’s 1998 death.
9. Crystal Harris & Hugh Hefner (60 years)
Hugh Hefner is infamous for dating younger women, but his relationship with playmate Crystal Harris really takes the biscuit. Married to the Playboy founder since 2012, Harris is, unbelievably, 60 years her husband’s junior. One year after their wedding, moreover, she told The Huffington Post that she tied the knot for “security” – much to nobody’s surprise.
8. Anna Nicole Smith & J. Howard Marshall II (63 years)
Though she first gained fame as Playmate of the Year 1993, Anna Nicole Smith is perhaps best known for marrying oil magnate J. Howard Marshall II in 1995. Then aged 89, Marshal died just 14 months later, leaving a $1.6 billion estate behind. Smith – 63 years his junior – spent years battling his family for a share of the estate before her own death in 2007.
7. Jerry Hall & Rupert Murdoch (25 years)
More than 15 years after ending her relationship with Mick Jagger, Jerry Hall hooked up with News Corporation mogul Rupert Murdoch in 2015. After meeting at a production of The Graduate, the duo – who have a 25-year age difference – married a year later. We can only imagine how different he is to the Stones’ frontman.
6. Amber Heard & Johnny Depp (22 years)
Pineapple Express star Amber Heard seemed to have hit a homerun when she bagged Hollywood hearthrob Johnny Depp in 2013. But, alas, things weren’t meant to be for them. Just one year after getting hitched and six years on from their first meeting on the set of The Rum Diary, Heard split with Depp – 22 years her senior – leading to an acrimonious legal battle.
5. Mia Farrow & Frank Sinatra (29 years)
As Mia Farrow’s first love, Frank Sinatra played a pivotal role in the Rosemary’s Baby star’s later life. Marrying when he was 50 and Farrow was 21, the legendary crooner divorced her in 1968 – just two years after their nuptials. However, the two continued to liaise until Sinatra’s 1998 death. In fact, Farrow even once said that he may be the biological father of her son Ronan.
4. Ashton Kutcher & Demi Moore (16 years)
One of showbiz’s most famous inter-generational marriages, Ashton Kutcher and Demi Moore enjoyed an eight-year relationship in spite of a 16-year age gap. After first meeting at a friend’s dinner in 2003, the screen stars would marry just two years later. Sadly, allegations of infidelity drove the two apart in 2011. Subsequently, Kutcher hooked up with Mila Kunis – five years his junior – in 2012.
3. Emma Heming & Bruce Willis (22 years)
Like his ex-wife Demi Moore, Bruce Willis has a thing for younger spouses. In fact, the Die Hard star’s current wife model Emma Heming – whom he met at the gym in 2007 – is 22 years his junior. Just two years after they started dating, the pair married, and they now have two children together.
2. Melania Knauss & Donald Trump (24 years)
It probably won’t shock anyone to learn that our current First Lady is younger than the commander-in-chief. But the revelation that former model Melania Trump is nearly a quarter of a century younger than her husband Donald is certainly surprising. Together since 1998, the two reportedly hooked up while Donald was taking another woman on a date.
1. Soon-Yi Previn & Woody Allen (35 years)
There may be a 35-year age gap between them, but that’s been the least of Woody Allen and Soon-Yi Previn’s issues. Indeed, the legendary comedian began dating his current wife while he was still married to her adoptive mother Mia Farrow – making Allen Previn’s stepfather! Nevertheless, the two have been wed since 1997 and their relationship has survived despite some intense public scrutiny.