A-List Couples Who Had Surprisingly Large Age Gaps

Zack Braff met Florence Pugh when he was 43 and she was 22. The story goes that he reached out to her on social media, but it's hard to know for sure. Either way, not long after, the two were dating and sharing their relationship openly via social media. They stayed together for four years, but they eventually called it off. Reportedly, one of the main reasons for the breakup was public criticism. 

Here's another high-profile relationship that involved a female superstar who was older than her partner. However, it shouldn't be surprising, considering Madonna is known for dating men younger than her. This one was with a Brazillian model named Jesus Luv, who was 21 when the relationship began. Madonna was in the middle of separating from Guy Ritchie at the time, but the relationship only lasted for a couple of years.

These two celebs met when both of them were acting in the hit show, Heroes. However, there was only one problem. Hayden Panettiere was only 17 at the time. After she turned 18, she and Milo Ventimiglia officially began their romantic relationship. They only dated for around two years after that, but Panettiere did address the age difference afterward, saying she never set out to date an older man. 

Melanie Griffith was very young when she and Don Johnson began their relationship. They only met because Griffith was the daughter of a fellow actress, Tippi Hedren when Hedren and Johnson were working together. They started living together only a year after they met, and they ended up getting married as soon as Griffith turned 18. Not long after, the couple split up, but that wouldn't be the end of the story. 

A lot of people probably don't know Joel Madden from his name alone, but he's the lead singer of a band you've probably heard of, Good Charlotte. He and Hilary Duff met when she was only 16, and they announced their relationship together a year later, which leads us to believe it started not long after they first met. A year after making it all official, they both called it quits. 

Johnny Depp and Winona Ryder's relationship was big news when it first came out that they were dating. They met when Ryder was around 17, but they wouldn't make things official until after she turned 18. Not long after that, they announced that they were going to get married, but the engagement lasted for around three years before the two eventually called things off. Still, by all accounts, they were head over heals for each other. 

While most of the relationships on this list involve older men and younger women, that doesn't mean there haven't been Hollywood couples that were the other way around. Fergie was 26 when she and Justin Timberlake started seeing each other. Timberlake was around 16. However, she's since said that the two weren't really all that serious. “Justin and I would go out together and have fun and make out,” she's said. 

If you've ever watched or heard of the hit show One Tree Hill, then you might be familiar with Chad Michael Murray and Kenzie Dalton. The two starred together in the show, meeting when Dalton was 17 and Murray was 26. They didn't waste any time, and the two were engaged almost immediately. In fact, Dalton was still in high school when they made their engagement announcement. However, the two did end up calling off the engagement. 

Tyga and Kylie Jenner actually met because Tyga was performing at Jenner's 16th birthday party, but they'd wait for another year to make it official. The two stayed together for a while, but they ended up splitting in 2017, at least partly due to Jenner's age. "There was no crazy fight; we just decided… Well, I decided that I’m really young,” she told an interviewer after the break-up became public. 

Who could forget Wilmer Valderrama from That ‘70s Show? He and Demi Lovato worked together for a public service announcement when he was still starring in the That '70s Show, but according to Lovato, they waited until she turned 18 to start dating. They stayed together for a good six years before finally parting ways. However, she still talks very fondly about their time together and how much she cares about him. 

This is probably one of the biggest age gaps on this list. Doug Hutchinson is an acting coach who met non-binary model Courtney Stodden when she was only 16. In fact, he asked Hodden's mother if he could coach her in acting, but it wasn't long before he asked for her hand in marriage. In fact, it was only around a week after meeting Stodden that he asked for a marriage. 

This one shouldn't come as much of a surprise if you're a fan of Taylor Swift. She and John Mayer dated when she was only 19 and he was 32. Unlike a lot of breakups on this list, their breakup was a bit messy, and both wrote songs about it that painted the other in a negative light. They weren't really even together all that long, but it continues to be a favorite subject among fans. 

Demi Moore was 41 when she and Ashton Kutcher started dating. Kutcher was still starring in That '70s Show at the time, and the two's relationship actually lasted for a really long time. They were together for six years and married for four of those years. They also spoke about the age gap in public, but as you probably know, things wouldn't last. They eventually filed for divorce, and Kutcher started seeing Mila Kunis a year later. 

Not many people think about it much now, but Jay-Z and Beyonce are another couple with a pretty wide age gap. Jay-Z was 31 when he met an 18-year-old Beyonce during a plane ride they took together. A year later, they made their relationship official, and the rest is pretty much history. They've had some ups and downs, but they're reportedly doing really well today and seem like the perfect match.

When it comes to Hollywood couples and age gaps, it's hard to think of a more iconic duo than Elvis Presley and Priscilla. She was only 14 when the two first met, but the relationship didn't officially begin until years later. Elvis was 24 when they met. They waited until Priscilla was 21 to marry, but they'd talked about marriage beforehand, according to Priscilla years later. She even relocated to Tenessee to be closer to Elvis when she was 16. 

A lot of people forget about Henry Cavill's relationship with Tara King. The two started seeing each other when King was 19 and Cavill was 32. At the time, she was just a college student. Things didn't last very long though, with both reportedly wanting different things. "she was in too deep, and he didn’t want anything too serious,” a source told the media not long after the split. 

When Harry Styles was just starting to make it big, he met Nicole Scherzinger. In fact, she was a judge when he and his band, One Direction, were competing in a contest. A couple of years later, it became official that the two were seeing one another. However, it didn't last long. Styles has dated a couple of women older than he is, but none with an age gap as wide as this one. 

Prince and Mayte Garcia's relationship didn't actually start until Garcia was 19, but they'd met years before when she was only 16. And Prince became her legal guardian so that she could travel to the U.S. only a year after that, so it's safe to assume they were seeing each other romantically around that time. They stayed together for four years after making it official, but they separated in 2000.

Comedian Dane Cook was 45 when he met his 17-year-old future wife, Kelsie Taylor, during a game night at a friend's place. They didn't officially start dating until she was 18. The two got engaged in 2022, and they were recently wed in Hawaii. The age gap is still a pretty regular topic, but they seem to be getting on well, and there isn't any sign of a split coming. 

There are plenty of wild stories on this list, but Anthony Kiedis, from the Red Hot Chili Peppers might just have the craziest. He's said that at one point when he was touring in his mid-20s, he met a fan and brought her along on his tour. However, according to him, it wasn't until later that she told him that she was only 14 years old. But, it gets worse. 

There was plenty of criticism from friends and family when it was announced that Scott Disick was seeing a 19-year-old Sofia Richie. Disick was 34 at the time. Richie's father is Lionel Richie, who made it clear that he wasn't a fan of the relationship, while Disick's Kardashian friends aired their grievances with the relationship publically as well. Luckily for them, the couple didn't last, and they broke up after three years. 

There are a lot of rockstars on this list who've had relationships with pretty wide age gaps, and Steven Tyler is another. He was around 26 when he and a 16-year-old Julia Holcomb first met. However, because she was so young, they couldn't travel together, so Holcomb's mother signed over guardianship to Tyler, and the two spent a couple of years touring with one another before they finally called it off. 

You may not be familiar with the name René Angélil, but you're probably familiar with who he married. Celine Dion met Angélil when she was 12, and he was 38. He was her manager, but the two didn't start seeing each other romantically until Dion was 19. Not long after that, they got engaged, but they tried to keep their relationship a secret due to the difference in their ages. 

Rockstar Jimmy Page first saw Lori Maddox through one of the photos she'd taken as a teen model. He reportedly asked that her manager bring her over so that the two could meet, with the manager avoiding the meetup a couple of different times. Not long after they met, they started dating, but it didn't last long as Page broke things off and started dating someone else. But he did try and keep their relationship a secret. 

Here's another one that not many people remember. Jerry Seinfeld was 38 when he first met a 17-year-old named Shoshanna Lonstein. She was still in high school at the time. There was a ton of criticism about the relationship at the time, but the two continued to see one another for a couple of more years. They were actually together for four years in all, but they ended up calling it quits. 

Charlie Chaplin and Lita Grey are another famous Hollywood couple that made waves when it was announced they were seeing one another. They worked together when she was only eight years old, but they didn't start seeing eachoter until years later, when she was 15. Not long after, Grey found out that she was pregnant, and the two were married in private. They would go on to have another child less than a year later.

There had to be something going on when One Direction auditioned for the X-Factor because Liam Payne is another member of the band who ended up seeing one of the judges. However, the two didn't start dating until years later, when Payne was 22. They were hot and heavy for a bit, having a child together before splitting up not long after. They're still on very good terms, according to reports. 

This is probably one of the most controversial and famous relationships on this list. A 22-year-old Jerry Lee Lewis married his cousin, 13-year-old Myra Gale Brown, in the late 1950s. The entire marriage was extremely troubled, and Brown filed for a divorce over a decade later, saying that Lewis was abusive and that she was “subject to every type of physical and mental abuse imaginable.” Today, she's a successful real estate agent and has remarried. 

Wilmer Valderrama and Lindsey Lohan were hot and heavy for all of half a year after they first met. Lohan was 18, and Valderrama was 24, but only a couple of months after going public with their relationship, they decided it was time to get married. The engagement didn't last very long, with both of them calling it off a few months later, but it was big news at the time. 

The Weeknd and Bella Hadid have had an on-again, off-again relationship from the start. They met and started dating when Hadid was 18, and The Weeknd was 25. However, they broke up not long after, and The Weeknd began dating Selena Gomez. Then, they got back together a couple of years later, only to call things off again. At the time of the breakup, both said that their different schedules made dating difficult. 

Woody Allen is known for his controversial relationships, and the one with Babi Christina Engelhardt is probably one of the more controversial. She was 16 and Allen was 41 when they first met. Allen has since said that he never asked her how old she was, but he did know that she was still in high school at the time. They stayed together for the better part of a decade, but they tried to keep their relationship a secret. 

Wilmer Valderrama appears a lot on this list. This time, it's for his relationship with Mandy Moore, who was only 16 when she met a 20-year-old Valderrama. The relationship only lasted for around a year, and the two are reportedly still on friendly terms. However, there were some comments made by Valderrama after the relationship ended that made quite a buzz. We won't repeat them here, but many said they crossed a line. 

Wanya Morris, the Boyz II Men singer, was in his early 20s when he agreed to take Brandy on as a protege. At the time, she was only 17, but he said that the relationship was strictly based on business at first. After she turned 18, the two realized they had feelings for one another, and they began dating. "We had been hanging around each other so much that there came to be some sort of connection. An intimate connection. We actually fell in love,” he said.