It's 2020, and famous people are always under the watchful scrutiny of the public. A poor political remark, a slightly offensive opinion, and even a minor mistake can get you canceled in a matter of weeks or even days! But somehow, the celebrities on our list have dated minors blatantly and got away without suffering the consequences. How have they done it, and why has no one made a big fuss about it? That's a mystery for us to explore.
But relax. You don't need to get your heart crushed just because your favorite actor or singer has made it to our list. Sometimes, it's okay to date someone a little bit younger than you, even if that person happens to be under 18. Make no mistake, though: there's still enough room for controversy in our surprising list, which features some impressive celebrity couples you probably don't ever remember were ever an item.
Fergie At Age 23 Dated Justin Timberlake When He Was 16
Justin Timberlake has always been a hunky man, even when he was just a 16-years-old boy rocking the heart of every teenage girl alongside his NSYNC mates. Back in the day, he was such a Casanova he even got the attention of singer Fergie, who at the time was a member of the girls-group Wild Orchid.
Their brief fling happened in 1996 and resulted in nothing serious. But it's surprising to find out a 23-years-old Fergie got her heart melted by Timberlake's sweet and kind 16-year-old eyes. Since then, Timberlake went on to date numerous other celebrities, such as Britney Spears and Cameron Diaz, while Fergie made it to a little band called The Black Eyed Peas.
Joel Madden At Age 25 Dated Hillary Duff When She Was 16
In 2004, the actress/singer Hillary Duff was one of the world's steamiest new teenage stars. But even though she was a stunner, she was only 16! But the fact didn't matter much to a 25-year-old Joel Madden, who at the time was topping the charts with his rock group Good Charlotte.
The odd couple dated for 3 years before breaking up. Since then, Madden has hooked up with the socialite Nicole Richie, who is now his wife. As for Duff, she's recently recalled her relationship with Madden, and she had nothing but good things to say about what she believed to be "a wicked good time."
R. Kelly At Age 27 Dated Aaliyah When She Was 15
Today, we know that the controversial marriage of the singers R. Kelly and Aaliyah was all but a "love has no age" type of situation. Back in the day, R. Kelly was not only Aaliyah's mentor, but also her main songwriter and, putting it shortly, the man who ran her career on what had to be a tight leash.
With so many unfathomable examples of abusive behavior now associated with R. Kelly, we're grateful Aaliyah was wise enough to divorce him in 1995, just one year after they first got married. In 2001, though, Aaliyah passed away tragically after being involved in a plane crash. She was only 22.
Wilmer Valderrama At Age 29 Dated Demi Lovato When She Was 17
This one is a shocker. The That '70s Show superstar Wilmer Valderrama is a well-known womanizer, and we all know he has a taste for the younger ladies. But a 12-years age gap may be too much even for him, especially considering the woman she was dating was under 18...
Valderrama and the teenage superstar singer Demi Lovato enjoyed a solid 6-years relationship, which started in 2010 and ended in 2016. Still, we're not sure if it's right for a mature man to date a girl who's so much younger and inexperienced than him. Since then, Demi has dated The Young and the Restless actor Max Ehrich, but the two have reportedly separated earlier this year.
Doug Hutchinson At Age 51 Dated Courtney Stodden When She Was 16
American actor Doug Hutchinson is known for playing disturbing characters in multiple movies and series. But his 10-years marriage to a woman 34 years younger than him may well be his most disarranged role yet. Doug married the model/singer Courtney Stodden when she was just 16, with the wedding being authorized and witnessed by Courtney's mother.
The odd relationship caused some controversy from the very beginning, with Doug and Courtney making it as a couple to multiple reality-series, such as Celebrity Big Brother. Now, Courtney has declared to be officially divorced from Doug and said in a recent interview that she felt "groomed" and "taken advantage of."
Jamie Walters At Age 23 Dated Drew Barrymore When She Was 17
Drew Barrymore was one of the most accomplished child actresses of the past few decades, and she had some fun with her bonafide fame while growing up. When she hit 16, she started revealing her most rebellious side, making engagement plans with two older men: actors Leland Hayward III and Jamie Walters.
In 1992, Drew got engaged with Jamie, who's best known for his role in Beverly Hills, 90210, few months after finishing things off with Hayward. Drew and Walters's plan of getting married didn't work out, and the two split-up in 1993. While dating, they had a quite significant 5-years age gap.
Justin Gaston At Age 20 Dated Miley Cyrus When She Was 15
She's always looked a bit older than she is, but 15-year-old Miley Cyrus was still way too young for her 20-year-old boyfriend, Justin Gaston. Back in 2008, the American singer-songwriter and the teenage sensation dated for a little less than a year, and their significant age gap was controversial even at the time.
In 2009, the young couple broke up, and the difference in their maturity was clear. Miley uploaded a sad message on Twitter saying, "tears are words the heart can't express," to which Gaston replied, "they've gotta run out soon, right?". That was a cold-hearted move, Justin!
Jimmy Page At Age 28 Dated Lori Mattix When She Was 14
The incredible story of the notorious rock & roll groupie Lori Mattix is not one for the faint of heart. Before turning 18, the former child model was canoodling with the likes of David Bowie, Mick Jagger, and... Jimmy Page. The latter, who was the lead guitarist of the legendary Led Zeppelin, was a 28 years-old man by the time he assumed a relationship with the 14-year-old groupie!
Besides nauseating, Page and Mattix's love story made news all over the U.S., and the authorities even got involved at a certain point! But you know what's even worse? 2 years after committing to Page, a 16-years-old Mattix called it quits after finding him in bed with another groupie: the American singer/model Bebe Buell.
Jerry Lee Lewis At Age 22 Dated Myra Gale Brown When She Was 13
You know it's bad when it's the '50s, and your marriage is still in the origin of a nationwide controversy. Back in the heyday of rock & roll music, it was not uncommon for minors to get engaged. But 22-year-old Jerry Lee Lewis pushed the bar way too low back when he decided to marry his 13-year-old first-cousin Myra Gale Brown.
The marriage cost Lewis many concert deals, which was more than fair. At 13-years-old, young girls are expected to be playing with dolls, not marrying their much-older cousins! The extremely controversial couple stayed together for about 12 years before divorcing in 1970.
Jerry Seinfeld At Age 39 Dated Shoshanna Lonstein When She Was 17
Bonafide comedian Jerry Seinfeld doesn't like to talk about it, but he dated a much-younger high-school student in the early '90s. Their relationship started when Shoshanna Lonstein was only 17, and she met Seinfeld after being reportedly "picked-up" by the comedian near her school. At the time, Jerry was enjoying success, as Seinfeld (the show) was one of the most popular comedy series in the world.
The 39-year-old man and the young student shared a passionate relationship that lasted all the way through Shoshanna's first college years. Shoshanna is now an accomplished fashion designer with 3 children, while Jerry's been married for years to the author/philanthropist Jessica Seinfeld.
Bill Wyman At Age 47 Dated Mandy Smith When She Was 14
Most 14-year-olds spend their days playing with friends and going to school. But not Mandy Smith. Unbelievably, she was dating a man who was 33-years her senior! Yes, the former The Rolling Stones' bassist Bill Wyman and the singer/model Mandy Smith were an item of despicable nature for years!
The two tied the knot as soon as Mandy turned 18, divorcing two years after. Mandy was later engaged to the Welsh footballer Pat Van Den Hauwe and the Vanity Fair model Ian Mosby. In 2010, she recalled her controversial relationship with the Wyman, mentioning she has since found love in the arms of God.
Milo Ventimiglia At Age 29 Dated Hayden Panettiere When She Was 17
In 2006, the TV series Heroes was a worldwide phenomenon, much due to the characters played by Milo Ventimiglia and Hayden Patteniere. But who could've guessed that the two actors, with a 12-years age gap, would eventually fall in love and become an item?
To be fair to Milo, Panettiere has later admitted that she has a liking for older men. On the other hand, Milo has revealed in a 2017 interview that he regrets dating the former Heroes superstar. After breaking-up with Milo, Panettiere has married and divorced the former professional Ukrainian boxer Wladimir Klitschko twice. He is 13 years older than her.
Don Johnson At Age 22 Dated Melanie Griffith When She Was 15
In 1972, actors Don Johnson and Melanie Griffith met at the set of the movie The Harrad Experiment. Melanie was only 14 at the time, but that didn't prevent Johnson from chit-chatting with the young girl. About one year later, the two actors became an item despite their 7-years age gap. And on Melanie's 18th birthday, they tied the knot for the first time.
Don and Melanie's love story may have started a little bit too soon, but it was meant to be! After divorcing in the same year they got married, the two actors reconnected and tied the knot for the second time in 1989. They have since divorced again, but they share a beautiful daughter you may have heard of: Dakota Johnson, the star of 50 Shades of Grey.
Woody Allen At Age 53 Dated Soon-Yi Previn When She Was 19
Strangely enough, the love story of celebrated director Woody Allen and Soon-Yi Previn wouldn't even make for a good Woody Allen movie... When you look at it, it sounds more like a Lars Von Trier type of plot! You probably know the story, as it's been making headlines since the early '90s: it's the tale of a much older man who dates and marries the adoptive daughter of his ex-girlfriend.
Twisted as it is, Woody Allen and Soon-Yi Previn have been married since 1997 and have continued to survive the widespread criticism of the public. Before dating Soon-Yi, Woody Allen was in a relationship with her adoptive mother, the actress Mia Farrow.
Elvis Presley At Age 24 Dated Priscilla Presley When She Was 14
It's one of the best-known love stories on our list. The teen idol Elvis Presley, still regarded as an ultimate American symbol, decided it was okay to marry a 14-years-old girl back when he was 24... A bold move only a man known as "The King" would ever be able to get away with.
To be fair to Elvis, he never married another woman after Priscilla, who's still busy taking care of Presley's priceless estate and cultural heritage. Elvis and Priscilla were an item between 1967 and 1973, but their special connection and friendship were ever-lasting.
Freddy Moore At Age 29 Dated Demi Moore When She Was 16
In 1981, a 17-years-old upcoming actress named Demi Guynes got married to the much-older musician Freddy Moore. That's how Demi Moore, the star of movies such as The Scarlett Letter and Mr. Brooks, got the name she's still known for today!
To make it all worse, Freddy and Demi met back when the actress was only 16, and the musician was married to another woman at the time. Between 1979 and their divorce in 1985, Freddy and Demi shared a torrid but highly-controversial relationship. Later, Demi made a name for herself as a Hollywood A-Lister and got married to the likes of Bruce Willis and Ashton Kutcher.
Shawn Andrews At Age 21 Dated Milla Jovovich When She Was 16
The Dazed and Confused actor Shawn Andrews has fallen under the radar in recent years. But back in the '90s, he was under the line of fire after deciding to marry a still-minor Mila Jovovich. The bombshell actress/model saw her premature wedding being nullified by her mother in 1992, the same year she first got the ring.
Things didn't work out for Shawn and Milla, but the Russian-born actress wasn't done with her series of controversial relationships. In 1997, she married the French director Luc Besson, a man we will tell you more about in just a sec...
Luc Besson At Age 32 Dated Maïwenn Le Besco When She Was 15
In France, the age of consent is 15 instead of the traditional 16, and that seemingly small fact has made a huge difference in this highly-controversial love story. Because at the very young age of 16, actress Maïwenn Le Besco gave birth to a child. And who was the father? None other than Luc Besson, a 17-years-older movie director!
Besson and Le Besco were married between 1992 and 1997, with Besson releasing his most successful movie in the meantime - Léon: The Professional. If you've never seen the movie before, let's say its plot is very likely inspired by a true story...
Wilmer Valderrama At Age 20 Dated Mandy Moore When She Was 16
When it comes to dating younger girls, Wilmer Valderrama is a repeat offender! He met the singer/actress Mandy Moore when she was only 15 and assumed a relationship with the young star by the time she was... 1 year older. Albeit not shocking, their 4-years age gap was significant given their ages.
In 2006, after Valderrama and Moore's 2-years relationship was over, the That '70s Show star gave an interview to Howard Stern in which he spoke quite arrogantly about his private life with Mandy. The American singer has since criticized Valderrama's behavior.
Chad Michael Murray At Age 24 Dated Kenzie Dalton When She Was 17
The American actor/model Chad Michael Murray is best known for his appearances in Dawson's Creek, Freaky Friday, and Riverdale. But did you know that the hunky actor was once involved with a 17-years-old girl?
It all started in 2005 when Chad first laid eyes on the Miss North Carolina Teen USA runner-up Kenzie Dalton. Their 5-years age gap didn't prevent them from smiling to the cameras on red carpet events and getting engaged in 2006. They never got to the altar, but they were an item for about 7 years before splitting up in 2013.
Paul Walker At Age 28 Dated Aubrianna Atwell When She Was 16
Not much is known about Paul Walker's ex-girlfriend Aubrianna Atwell, except she was only 16 when she first started dating the 28-year-old actor. Later, Paul would get involved with Jasmine Pilchard-Gosnell, another 16-year-old, which shows a pattern to the late actor's relationships.
After his death, Paul has been remembered kindly by the public and generally praised in the media. However, there was something extremely wrong about Walker's tendency to date minors so fast and so furiously. According to Aubrianna, she and Walker were an on-and-off couple for years before parting ways.
John Derek At Age 46 Dated Bo Derek When She Was 16
Not all of our love stories have a sad ending. The lovebirds' John and Bo Derek may have had a 30-years age difference, but that didn't prevent them from staying together until the very end. When actor John Derek passed away in 1998, his wife of 20-plus years, Bo, was still sitting right there next to him.
The two met back when Bo was modeling, and John was so impressed by the 16-year-old beauty he decided to leave his wife Linda Evans for her. Bo has since declared she felt bad for being the reason behind John and Linda's divorce, but it's a fact Bo and John were meant for one another.
Steven Tyler At Age 27 Dated Julia Holcomb When She Was 14
You may recognize Aerosmith's lead singer Steven Tyler for his decades-long career and excellent high-pitched vocals. But did you know he was involved with a 14-year-old fan back in the '70s?
Her name was Julia Holcomb, and she has since become one of rock & roll's most notorious groupies. Her love story with Tyler ended quite abruptly, following a shocking abortion, and the singer has later admitted he feels extremely regretful of his actions towards the young girl. After the break-up, Holcomb disappeared for a while but has recently made a name for herself as a motivational speaker.
Wilmer Valderrama At Age 23 Dated Lindsay Lohan When She Was 17
We're starting to think Wilmer Valderrama likes to fall in love with under-18 women on purpose. With a whopping third entry on our list, the That '70s Show womanizer was once the love interest of the early 2000's "it" girl Lindsay Lohan.
Back in the day, Valderrama was still trying to make it into the exclusive Hollywood elite, while 17-year-old Lohan seemed like she was about to conquer the entire world. Sadly, both actors never fully realized their potential, and we wonder if their controversial early-2000's fling was the reason why their careers got jinxed.
Kobe Bryant At Age 21 Dated Vanessa Bryant When She Was 17
You know the drill: a highly-accomplished basketball superstar meets an under-18 back-up dancer and makes her fall for him. But while many adult men love to take advantage of younger, more innocent girls, that was not the case in Kobe and Vanessa Bryant's love story.
In fact, these two shared an exemplary relationship from 1999 until 2020, the same year in which Kobe died tragically in a helicopter accident. The basketball legend and the former dancer were married between 2001 and 2020 and had 4 daughters together, including Gianna-Marie Onore, deceased earlier this year.
Paul Walker At Age 33 Dated Jasmine Pilchard-Gosnell When She Was 16
It's simple math: at the time of his tragic death, 40-year-old actor Paul Walker was dating a 23-year-old woman named Jasmine Pilchard-Gosnell for about 7 years. Which means they were an item since the time Jasmine was only 16...
Paul and Jasmine's romance got some attention in the media earlier this year, with journalists calling for a much-needed reflection on the subject. Even though his fans and family dearly remember Walker, his history of dating much-younger women must not be ignored. As Goat.com's Alexander Pan has put it, "it's complicated, but we need to talk about it."
Wanya Morris At Age 21 Dated Brandy When She Was 15
When a 15-years-old Brandy, then an upcoming singer, was invited to tour with Boys II Men, one of the world's top R&B acts, she couldn't believe it! But the experience only got more intense for the young superstar after she fell in love with Boys II Men's singer Wanya Morris, a 6-years-older man.
She confessed her feelings to Morris, and the two started a relationship. In a recent interview, Brandy said she felt "true love" for the Boys II Men's singer, but there's a good chance the feeling wasn't mutual. Unbelievably enough, Morris was the one who broke-up with Brandy after falling in love with another woman.
Taylor Swift At Age 23 Dated Harry Styles When He Was 18
Taylor Swift's dating history is as rich as her incredibly-successful discography, but her love stories, unlike her singles, don't always land in the number 1 spot. In 2012, the American singer-songwriter was dating the much-younger musician Harry Styles, who had just become a man...
We know; Harry was not a minor. But he was so "barely legal," we felt he should be included in our list! Quite predictably, Taylor Swift and Harry Styles's love story didn't last for more than a couple of months, with both musicians parting ways in the same year they first became an item.