Love knows no boundaries, especially when it comes to age. Chances are, you've experienced or witnessed a relationship where the partners weren't close in age, and while it can make some people pause, for others, it's hardly worth mentioning. In the world of Hollywood, relationships with notable age gaps are practically the norm. Some of these famous pairs have years, even decades, between them—begging the question: did the age difference strengthen or strain their bond? Dive in to find out how these celebrity couples fared.
Zach Braff (43) And Florence Pugh (22)
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.
The two are still friends, and they both say that they talk to one another regularly and that they often root for each other when they have interviews or public appearances.
Madonna (49) And Jesus Luz (21)
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.
The two called it quits in large part because of the age difference, according to them. Today, Madonna is in a relationship with a much younger Josh Popper, who was 29 when they started dating.
Milo Ventimiglia (29) And Hayden Panettiere (17)
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.
"It was never a case of me making a decision, saying, ‘I want to date older men.’ But I am drawn to people who make me up my game, who bring me up to their level,” she said.
Don Johnson (22) And Melanie Griffith (14)
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.
They'd end up remarrying a little over a decade later, which is when they had Dakota Johnson, but the second marriage wouldn't last. Despite all of that, both still say that they're close friends.
Joel Madden (25) And Hilary Duff (16)
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.
Another year later, Madden was dating Nicole Richie. That relationship did last, and today, the two have a couple of children together, and they're still going strong by all accounts.
Johnny Depp (26) And Winona Ryder (17)
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.
Depp even got her name tattooed on him but ended up having to change the tattoo after they called off the wedding. It goes to show that even celebrities make mistakes.
Fergie (23) And Justin Timberlake (16)
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.
Fergie was one of the first high-profile relationships Timberlake had when he was just starting to make a name for himself, and he'd later go on to date Britney Spears.
Chad Michael Murray (26) And Kenzie Dalton (17)
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.
But they would try and make it work for several years before officially splitting up. The breakup was private, and it wasn't actually made public until months after it happened.
Tyga (24) And Kylie Jenner (16)
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.
Jenner would later go on to date and have a child with Travis Scott. That relationship would last around five years, before the two eventually separated and called it quits.
Wilmer Valderrama (29) And Demi Lovato (17)
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.
Lovato has even referenced the age gap in one of her songs, but she said that the difference in age was a toxic part of the relationship and that she wouldn't recommend it to anyone.
Doug Hutchison (50) And Courtney Stodden (16)
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.
The entire relationship was reportedly pretty troubled, with Stodden wanting a divorce a couple of different times, but it wasn't until 2018 that the two finally ended up filing and making it official.
John Mayer (32) And Taylor Swift (19)
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.
The song "Dear John" by Swift talks about dating an older man named John, and it was released after the breakup, so many have concluded that it was a direct reference to just that.
Demi Moore (41) And Ashton Kutcher (25)
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.
Moore is still acting, but she hasn't remarried since her split with Kutcher, but she is reportedly dating a chef, named Daniel Humm and the two are very happy.
Jay-Z (31) And Beyoncé (18)
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.
The two have three children together, and they're probably one of the most iconic power couples in the business. And it all started because they happened to sit next to one another during a plane ride.
Elvis Presley (24) And Priscilla (14)
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.
They had their daughter, Lisa Marie, not long after marrying, but the two would eventually split a couple of years later due to infidelity on both sides, according to interviews years later.
Henry Cavill (32) And Tara King (19)
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.
King has mostly vanished from the spotlight, but when the two were dating, things were reportedly going really well and they only ended it because both were looking for different things.
Nicole Scherzinger (35) And Harry Styles (19)
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.
Since they split, both have referred to their relationship as more of a fling than anything serious, and it's unclear if they still talk regularly with one another or not.
Prince (32) And Mayte Garcia (16)
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.
The two split after their child passed away not long after birth due to a rare genetic disorder. Today, Garcia is a dancer and actress and she lives in the U.S.
Dane Cook (45) And Kelsi Taylor (17)
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.
Taylor is a fitness instructor, and she posts about her healthy lifestyle habits on social media pretty often. She also recently began dabbling in singing, which she has a background in from when she was younger.
Anthony Kiedis (Mid-20s) And A Fan (14)
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.
He said that her father was also the chief of police for a town in Louisiana. However, Kiedis spent another night with the fan before finally taking her home the next day.
Scott Disick (34) and Sofia Richie (19)
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.
Today, Richie is married to Elliot Grainge, a record producer, and the two are reportedly very happy together. Disick is now dating Kimberly Stewart, who is a businesswoman and socialite.
Steven Tyler (26) And Julia Holcomb (16)
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.
A couple of years ago, Holcomb sued Tyler for assault, which she said happened when the two were dating, but the litigation in the case is still pending.
René Angélil And Celine Dion
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.
They stayed married until Angélil died in 2016, having three children together. Despite being a superstar, it's not clear if Dion is seeing anyone, but we do know that she has not remarried.
Jimmy Page (28) And Lori Maddox (14)
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.
Maddox also saw David Bowie before Page, and she has since said that she didn't see anything wrong with the age difference at the time but that now it does feel conflicted.
Jerry Seinfeld (38) And Shoshanna Lonstein (17)
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.
Today, Lonstein is a successful writer and designer, and she's been married since 2003. Seinfeld ended up meeting the woman who would become his wife the same year he and Lonstein broke up.
Charlie Chaplin (35) And Lita Grey (15)
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.
However, the relationship wouldn't last, and they broke up in only a couple of years due to infidelity. Grey would go on to have a very successful acting career before passing away in the 1990s.
Cheryl Cole (24) And Liam Payne (14)
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.
Cole is not currently dating anyone and has said, "I am learning that I can be absolutely fine without anybody, just me by myself." Payne recently started singing solo and plans on touring.
Jerry Lee Lewis (22) And Myra Gale Brown (13)
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.
Lewis went on to have a total of seven different marriages, and they were all pretty troubled, according to his former partners. He passed away in 2022, but he hadn't been in the public spotlight for years.
Wilmer Valderrama (24) And Lindsay Lohan (18)
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 two stars were immensely popular when they started seeing one another. Lohan wouldn't be Valderrama's last relationship with a pretty wide age gap, either. Today, Lohan is married to Bader Shammas.
The Weeknd (25) And Bella Hadid (18)
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.
They also said that they were still close friends and that they hadn't broken up because of a fight or anything else like that. Today, Hadid is dating Adan Banuelos, a champion horse rider.
Woody Allen (41) And Babi Christina Engelhardt (16)
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.
She recently shared her story with the Hollywood Reporter, saying, “This is not ‘bring down this man.’ I’m talking about my love story. This made me who I am. I have no regrets.”
Wilmer Valderrama (20) And Mandy Moore (16)
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.
The former That '70s Show actor did eventually apologize, though, and the two aren't enemies or anything. Today, Moore is married to Taylor Goldsmith and she just had her second child.
Wanya Morris (Early 20s) And Brandy (17)
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.
Brandy went on to have a very successful singing and acting career and, more recently, worked as a judge on The Voice. She's also received numerous awards for her achievements throughout the years.