Just about everyone is looking for love out there, and even more have tried dating. We all know there are certain restrictions on who we date, but there are also unofficial rules tht pretty much go unspoken because we all know not to do these things. We're talking about the weird thing where much older people date younger women. It is by no means illegal, and can sometimes be fruitful, but it's still strange. There have been a number of celebrities who dabbled in this trend. If you'd like to know who, we compiled a list just for you. Check it out below.
Elvis Presley
Everyone knows who Elvis Presley was. He was arguably one of the most influential singers of all time. But what you might not know is that before he and his wife, Priscilla, got married, they actually dated for a long time. They had met at a party in Bad Nauheim, Germany when Presley was in the Army and, at the time, Priscilla was only fourteen years old.
After they had dated for a while, her parents urged them to get married. Although she seems to have been too young at the time, she maintains that they waited until marriage before doing anything together.
Jerry Seinfeld
Before Jerry Seinfeld got married to his current wife, Jessica Sklar, he actually began to date another younger woman. He met Shoshanna Lonstein after approaching her in Central Park while on a walk. She was only seventeen at the time while Seinfeld was thirty-four. After exchanging numbers, they began to date pretty seriously, but their relationship came to a close after she graduated college.
He eventually met Sklar, who was closer to his age, in 1998. They must have really hit it off because they have been married to each other ever since.
Robin Thicke
After the success of his single, "Blurred Lines", Robin Thicke seemed to hit a rough patch in his life. He had struggled with substance abuse, got sued for unauthorized use of Marvin Gaye's track, and ended up splitting up with his wife in the midst of all the craziness (let's also not forget that performance at the VMAs he did with Miley Cyrus). He also unsuccessfully vied for his ex's forgiveness.
After everything went down, he was seen in his car with seventeen-year-old April Love Geary, and the two began dating. They have been together since and have actually had a few kids as well.
Luc Besson
This director began dating Maïwenn Le Besco after his divorce from his wife, Anne Parillaud, in 1991. Le Besco was only fifteen when they began seeing each other! He says that their relationship inspired his 1994 movie Léon: The Professional. They even got married, but that only lasted until his time working on "The Fifth Element" when he began to get involved with actress Milla Jovovich, who herself was twenty-two.
Maybe it's for the best that they split up. After all, not only was Le Besco underaged, but Besco was at least double her age. That's a bit scary to think about.
R. Kelley
While he may have come under a lot of fire recently for his behavior towards minors, we're talking about his relationship with the singer Aaliyah back in the 90s. He had been introduced to her as a "mentor" and he helped her produce her first album "Age Ain't Nothing But a Number", a title that seems a bit too coincidental for their relationship with each other.
They both denied being anything but platonic with each other, but secretly married in 1994. This marriage, however, was annulled due to her age.
Wilmer Valderrama
Wilmer Valderrama actually seems to make it a habit to date younger teens. Though he began not that much older than his first partner, Mandy Moore (she was sixteen and he was twenty), it was still questionable, but as long as they weren't doing anything illegal it could have been passable. Then he dated Lindsay Lohan when she was seventeen and he was twenty-four, and eventually settled for seventeen-year-old Demi Lovato when she was seventeen and he was thirty.
They began dating on and off for a few years, but we think that he might want to consider keeping himself reserved for women who are a little older.
Taylor Swift
In the early years of Swift's career, she decided to try her hand at a younger crowd. Although it wasn't too many years between her and Conor Kennedy, JFK's great-nephew, she was twenty-two at the time while he was only eighteen years old. Despite that not being such a crazy age gap, she still received some backlash. Their relationship, anyhow, only lasted a summer.
The reason they broke up, however, was not do to the age difference, but rather a gap in their distance. She has since moved on to many other potential candidates.
John Mayer
It turns out that Taylor Swift was, herself, the romantic interest of a much older man. She had begun dating John Mayer at the age of nineteen. He himself was thirty-two at the time. While, to be fair, he definitely had a much larger age gap than she did with Conor, it's hard to miss the irony that she came out with a song bashing Mayer for the age gap when she herself dated a younger man as an adult.
Moreover, as a nineteen-year-old, we think she would have had enough of a sense to make her own decisions and not feel pressured into dating someone too old for herself when she's nearly an adult as well.
Joel Madden
Joel Madden and Hilary Duff were also pretty adamant about how platonic they were. That is, of course, until Duff made it to the ripe old age of eighteen in 20016. That's when the whole dynamic changed. Although she never really stated what went on before they were officially together, she was quoted as saying in an interview with Cosmopolitan., "I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing".
We're not going to be making any assumptions here. We don't want to play into the whole thing, but as long as no one was hurt and they're happy with what they did, so be it.
Kobe Bryant
Elvis Presley wasn't the only one, apparently, who dated their wife before they were technically old enough. We do have to say that they weren't all that far off from being legal and their age difference wasn't that crazy (Bryant was 21 and his wife, Vanessa, was seventeen). They ended up married six months later and had a few kids together as well, though it wasn't all without its drama.
Unfortunately, the headlines made about their relationship would end up being the least of the family's concerns. We hope he's resting in peace wherever he is.
The Weeknd
Back in 2015, The Weeknd dated Abel Tesfaye, a model who, at the time, was only eighteen years old. He had expressed interest in working with her and the two got together rather inconspicuously. They would continue to date for over a year and a half, but then they eventually separated due to having scheduling issues. Coincidentally, they both appeared separately at the Victoria's Secret Fashion Show shortly afterward.
Talk about awkward. Meeting your ex at a fashion show just weeks after breaking up has got to be one of the worst things to happen. They were probably fine with it, though.
Nick Lachey
These two are probably most well known together for their show "Newlyweds: Nick and Jessica". What you might not know is that they had quite a few years difference between them. At the time of their meeting, Simpson was eighteen years old while Lachey was twenty-five. Unfortunately, their marriage wouldn't last very long (and subsequently, neither would their show). They divorced each other after only three years in 2005.
These days, Lachey spends time with his wife, Vanessa, whom he married back in 2011. They are certainly closer in age, but much closer in love.
Tyga
Back in 2014, Tyga began seeing Kylie Jenner of the hit reality show "Keeping Up With the Kardashians". They were only "hanging out" a lot at first, as Kylie was only sixteen at the time and Tyga was 24. Afterwards, they dated back and forth for some time but became much more personal when Kylie turned eighteen. He definitely received a lot of flack for this relationship.
It didn't last all that long, though. Eventually, Kylie would go on to be with Travis Scott whom she had a child with in 2018.
Chad Michael Murray
Chad Michael Murray met his youthful partner, Kenzie Dalton, when she was an extra on "One Tree Hill". At the time, she was still a senior in high school and was only eighteen years old when he proposed to her. Murray was 25-years-old at the time. They ironically remained engaged to one another for seven years, which is the same number of years apart they are from each other.
This wasn't the first time he experienced heartbreak. He had divorced his ex-wife, Sophia Bush, the same year they began dating. Eventually, he would go on to marry his current wife Sarah Roemer.
Sam Taylor-Johnson
Four years after her divorce to Jay Jopling, Director Sam Taylor-Johnson married her current partner Aaron Taylor-Johnson. The year before, when they had started dating, Aaron was only nineteen years old. Care to guess how old Sam was? She was forty-two at the time. Despite having a huge difference in their age, Aaron considers himself an "old soul" and claims not to really notice the difference at all.
We're guessing that's not entirely true, but if he's happy, then we're happy. We just wonder what brought them together in the first place. Time to do some research.
Doug Hutchison
If you thought that the age difference between the last two was surprising, wait until you hear this one. When Doug Stodden married Courtney Stodden, he was fifty-one years of age and she was only sixteen. Unsurprisingly, they needed Stodden's parents to sign off on the marriage. They had apparently married in Las Vegas after they met online. Since their marriage, they went through a lot of hard times together.
Eventually, in 2020, after being married for nine years, the two filed for divorce. We wonder how they are going to move on from their certainly strange and very public cross-generational relationship.
Justin Gaston
Justin Gaston Met with a sixteen-year-old Miley Cyrus after her father introduced the two of them. At the time, he was twenty years old. Although they only dated for a little less than a year, no one really paid any attention to it because we still hadn't seen the side of Miley that we do today. After all, she was still working with The Disney Channel.
Nowadays, they're doing their own things. We're not sure what Miley's life would have been like if they had stayed together, but if it changed who she is today we're kind of happy it turned out this way.
Dane Cook
Comedian Dane Cook began dating Kelsi Taylor in 2017. At the time, she was nineteen and he was forty-five. For a few years, they had kept their relationship pretty private, and that's not surprising considering they have a whole twenty-six years between them. Nowadays, they are still together, but they have to keep a chin up about they're age difference, but that's probably not so hard for a comedian.
Today, they are still happily partnered with each other. It seems they are destined for great things since they've been able to work it out. Although she's still young, the older they get the less weird it'll seem.
Scott Disick
Scott Disick from "Keeping Up With the Kardashians" started dating Sophia Richie in 2017 when she was nineteen years old. This came only two years after breaking up with Kourtney Kardashian herself. He was thirty-four when they started their relationship, but, clearly, that didn't matter to them. Apparently, though, they didn't have the best time together because, despite being initially very happy together, they broke up in 2020.
He was dating another nineteen-year-old in February--Amelia Hamlin, who is the daughter of Real Housewives of Beverly Hills star Lisa Rinna and actor Harry Hamlin. They broke up pretty soon, however.
Don Johnson
The actor who played Sonny on "Miami Vice", Don Johnson, began dating Melanie Griffith when she was fifteen years old. At the time, he himself was twenty-three years old. She is actually the child of his Harrad Experiment co-star Tippi Hedren. They went on to marry the next year, divorced the same year, then they got back together in 1989. However, they only spent another seven years together before getting divorced.
Together they had one child, Hollywood actress Dakota Johnson. Today, Don is married to Kelley Phleger. They got married back in 1999 and have been married ever since.
Steven Tyler
The lead singer of Aerosmith, Steven Tyler had begun dating Julia Holcomb when she was only sixteen years old. At the time he was twenty-six years old and in order for them to travel together across state lines, he became her legal guardian. Talk about being desperate for love. They had planned to get married but Tyler's family didn't approve. Still, they continued to date for a few years.
Shortly after Holcomb became pregnant with Tyler's child, they broke up. This is because he pressured her into getting an abortion and it put a strain on their relationship.
Jerry Lee Lewis
This one is one for the ages. Jerry Lee Lewis got married to his thirteen-year-old cousin, Myra Gale Browne all the way back in 1957. He was twenty-two at the time. But that wasn't all; they apparently got married even before his divorce from his second wife was finalized. He also had still believed in Santa Claus according to some reports. What an odd man he was.
Still, despite all the controversy and damage to his career that this stint caused, he and his cousin remained married for thirteen years and even had two kids together.
Fergie
When Fergie was twenty-three years old, she began dating Justin Timberlake. He was only sixteen at the time. Despite having declined to comment on the relationship on a guest appearance on the show "Watch What Happens Live with Andy Cohen", she later told Cosmopolitan, "Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr. Right Now".
You may have heard about this relationship, but at this point in time, it's old news. Now Fergie is on to bigger and better things like her infamous National Anthem performance.
Bill Wyman
A member of The Rolling Stones, Bill Wyman began dating Mandy Smith when she was thirteen years old. At the time, he himself was forty-seven. He admitted that they began having intimate relations when she was just fourteen years old and that they got married when she was eighteen. He had since admitted in his biographical film "The Quiet One" that the marriage was a mistake--they officially divorced in 1993.
We're not surprised to hear that their marriage ended in failure. He didn't speak about it, but the troubles of having an intimate relationship with a teenager is probably to blame.
Caroline Flack
We all know about the relationship between X Factor judge Caroline Flack and Harry Styles who was a contestant on the show when he was seventeen. At the time of their relationship, flack herself was already thirty-one. She has admitted that dating a man as young as himself was "quite strange" but she also said that she was never going to apologize for it. You go, girl?
But she's not the only one who got in on the action. Another X Factor judge--Nicole Scherzinger, who helped bring One Direction together--also dated him. We guess he was always a popular one.
Jimmy Page
Jimmy Page seems to have a thing for dating younger women. In 2015 he was dating 25-year old actress Scarlett Sabet at the age of 71. But if that's wild, there's another relationship that really stands out. In 1974, the Led Zeppelin guitarist reportedly kept some sort of relationship with Lori Maddox who was fourteen while he was thirty. They did break up after a year, though due to her age.
Even still, it seems like he'll never give up chasing the young ones. While they're not teens anymore, he still keeps it up. Better watch out, girls, he's coming for you even now.
Woody Allen
There's a lot of controversy surrounding this director. In 1976, when Allen was forty-one, he dated Babi Christina who was only at the tender age of sixteen. Actually, this relationship seems to be part of the inspiration for the character Tracy in the movie "Manhattan". But that's not all, who could forget his marriage to his ex's adopted daughter Soon-Yi Previn? Probably nobody, that's who.
.How could you even think to marry the daughter of your partner? Even though she's adopted and technically not his child eitherthat doesn't make it right. It's just weird.
Paul Walker
Although you might not have known this, actor Paul Walker had a streak for dating younger women. In 2001, he was dating Aubrianna Atwell, a sixteen-year-old, while he was 28. They even continued their relationship to the point where they moved in together. After that was over, he began dating another high school, Jasmin Pilchard-Gosnell, who was also sixteen. They were still dating when he died in that tragic car accident.
Although it's really sad, it's highly possible that no one ever talks about his track record because of his early demise. Still, it's hard to look past that sort of thing when you know about it.
Prince
Speaking of people who died young, Prince was also into the whole younger girls thing. Although, like some of the others on this list, it ended up turning into an actual marriage that lasted until the day he died, so the potential to overlook it is there. According to his wife, Mayte Garcia, they began dating when she was sixteen, and moved in together at seventeen when he became her legal guardian.
When she was nineteen he reportedly told her to go on birth control so that he could take her virginity. Seems he had a lot of patience to get a young girl to be with him.
Milo Ventimiglia
The star of "This Is US", Milo Ventimiglia, apparently began dating his "Heroes" co-star, Hayden Panettiere, when she just turned 18 years old. At the time of their relationship, he was thirty years old. They were talked about in the news for the whole two years that they dated before breaking up in 2009. However, he did mention in an interview that he would never do it again.
Seems like, for him, all the attention didn't really seem to click. We think that he'd be a lot more comfortable these days sticking to the women that are closer to his age.
Joaquin Phoenix
Although he had a legitimate interest in his current partner since 2012, they hadn't officially gotten engaged until 2019. Up until late that year, Phoenix had been dating a woman of whom he was 20 years her senior. Not only that, but she was still a teenager having been only nineteen at the time. They eventually broke up, and he got together with his wife Rooney Mara and they have a son together.
It seems these two will never be apart again. After everything he has been through to get together with her, we think they'll probably stay this way for a long time.
Rick Springfield
The star of "The Exorcist", Linda Blair, reportedly lost her virginity to the self-proclaimed "penniless musician" when she was only fifteen and he was twenty-five. Apparently, Blair approached Springfield at his show at the Whiskey, A Go Go nightclub in the 70s. They seemed to really hit it off. So much so that they ended up going back to his apartment that very same night.
They both seem to have very different opinions on the affair. Springfield thinks they took on the media storm head-on, while Blair believes they were pretty quiet about it. We think it was probably a mix of both.
Marvin Gaye
The famous singer, songwriter, and producer Martin Gaye also seemed to have met his wife, Janis Hunter, while she was very young. They met at a recording studio in Los Angeles in 1973. He was thirty-four at the time and Hunter was seventeen. After expressing an interest in her, they got together and married four short years later. Although they loved each other a lot, Janis wrote about it somewhat differently in her memoir.
She said that she loved Martin, but their relationship was turbulent. They had apparently both been addicted to drugs and sex, which is obviously not a formula for an outstanding relationship.