From Elvis Presley To Brad Pitt, Here Are 12 Male Celebs Who Have Dated Teenage Girls

Our society often likes to say that “girls mature faster than boys”. But one may wonder: when should a line be drawn?

Famous men have often, throughout history, pushed the limits of questionable age gaps when choosing a romantic partner.

Pictolic takes a look at 20 male celebrities who were well into adulthood when they started dating teenage girls.

12 PHOTOS

#1 Prince And Mayte Garcia

In the early 1990s, music superstar Prince, then aged 32, reportedly started dating 16-year-old dancer Mayte Garcia.

According to various sources In 1990, the Purple Rain singer saw Mayte standing outside his tour bus and referred to her as his "future wife" when pointing her out to bandmate Rosie Gaines. 

The late music icon married Mayte when he was 37 and she was 22, in a ceremony that took place in Minneapolis at Park Avenue United Methodist Church, which Prince attended when he was younger.

In Mayte’s 2017 book, In The Most Beautiful, Mayte revealed that after she graduated high school in Germany, Prince became her legal guardian.

She wrote: “I was married to him. There’s a level of respect you want to hold.

“I worked for him as well. I met him when I was 16.

“My father gave him legal guardianship over me. It was a different relationship than his other employees had.”

According to her accounts, Mayte was instructed by the musician to get on birth control when she was 19, subsequently starting a sexual relationship.

#2 Elvis And Priscilla Presley

King of rock and roll Elvis Presley was infamously much older than his future wife when he first met her.

Elvis started dating Priscilla when he was 24 and she was a 14-year-old teenage girl.

Despite a questionable age gap which would’ve definitely been condemned by the law in most countries, Priscilla has said that the 10-year age gap between her and Elvis “wasn’t as much of a problem as it seems like it was on paper”.

During a press conference in September for the upcoming movie Priscilla, Elvis’ former wife explained that her parents had a hard time understanding why Elvis was “interested” in her, but she thinks it was because she was “more of a listener” than other people he had met and that he was able to openly share his thoughts and feelings with her.

“Even though I was 14,” Priscilla recalled, “I was actually a little bit older in life. Not in numbers.”

Priscilla claimed that the music legend “respected” her age when they first got together, saying they didn’t actually have sex until later (they didn’t get married until she was in her 20s) and that he was “very kind, very soft, very loving” with her.

#3 Charlie Chaplin And Lita Grey

Powerful famous men dating minors is a problem that has persisted in the entertainment industry for quite some time.

In fact, cinema pioneer Charlie Chaplin met child actress Lita Grey in the 1920s.

In 1924, while filming The Gold Rush at the age of 16, Lita notably caught Charlie’s eye, who was 35 at the time.

A romance between Lita and Charlie developed as a result of shooting the movie, which led to marriage in Mexico on November 26, 1924.

But this marriage was hastily arranged, as Lita was pregnant.

Charlie and Lita went on to have two children during their marriage, which ended in 1926.

#4 Demi Lovato And Wilmer Valderrama

Last month, popstar Demi Lovato appeared on The Howard Stern Show where she opened up about dating older men and being motivated by "daddy issues".

She recalled: “I look back on the past and think, 'That’s gross. I was a teenager.'

“And so, to me, that’s gross.”

Demi didn’t name any specific person, but it is highly likely that Wilmer Valderrama was in her thoughts at the time of the interview.

That '70s Show actor was reportedly 29 when he started dating 17-year-old Demi.

Last year, the singer appeared to reference Wilmer in her song “29”, which includes the lyrics: "Finally 29 / Funny, just like you were you at the time,

"Thought it was a teenage dream / Just a fantasy / But was it yours or was it mine / 17, 29.”

#5 Steven Tyler And Julia Holcomb

#6 Anthony Kiedis And Ione Skye

Before rising to fame as the lead singer of the Red Hot Chili Peppers, Anthony Kiedis was implicated in a suspicious relationship with then-up-and-coming film actress Ione Skye.

Anthony and Ione, who became best known for her role in 1989’s Say Anything, began dating when they were aged 24 and 16 respectively.

Ione had a tumultuous childhood and had little contact with her father growing up.

Nevertheless, Anthony also claims to have undergone a troubled childhood, as he described in his memoir Scar Tissue being the son of a Hollywood drug dealer and therefore being exposed to drugs, sex, and alcohol from a young age.

In a TikTok, Ione said: “I was 16 going on 17.

“Do I approve of this age gap? No, not at all.

“Also, my mother and brother, who I grew up with, were very disapproving at that time.

“They absolutely tried to talk me out of it ten thousand times.

“They very much did not approve and were very alarmed.”

#7 Jimmy Page And Lori Maddox

Lori Maddox was born in Los Angeles in 1958, and at 13 years old, she started to spend time in the 1970s rock and roll scene.

She became a regular at quintessential rock venues at the time, including the Rainbow Bar & Grill, Rodney’s English Disco, the Continental Hyatt House (the notorious “Riot House”), and the Whisky A Go Go.

Lori became a teen model for various magazines, notably the Star magazine, the most popular of the time. 

As her physique attracted many admirers, she reportedly lost her virginity to David and Angie Bowie at 13.

When a photo of her was shown to then-28-year-old Jimmy Page, the guitarist and founder of the rock band Led Zeppelin, became infatuated with the teenage girl.

The young model continuously dismissed Jimmy’s advances, as she revealed that she was afraid of the rock star.

Eventually, Led Zeppelin’s tour manager “kidnapped” her and brought her to Jimmy’s room at the Hyatt.

In an interview for the Hammer of the Gods, a biography of Led Zeppelin, Lori Maddox said that the room “was dimly lit by candles… and Jimmy was just sitting there in a corner, wearing this hat slouched over his eyes and holding a cane.

“It was really mysterious and weird… He looked just like a gangster. It was magnificent.”

Jimmy and Lori kept a secret love affair, due to the teen’s young age and the fact that the guitarist was in a relationship with famous groupie Pamela Des Barres.

However, Jimmy’s relationship with Pamela dramatically ended when he attended a party with her, but left with Lori.  

Reports revealed that Jimmy and Lori were in love. Nevertheless, when Lori turned 16, Jimmy left her for playmate Bebe Buell.

#8 Jerry Seinfeld And Shoshanna Lonstein

Jerry Seinfeld’s relationship with Shoshanna Lonstein has become a viral topic lately, with many people reacting with shock after learning Jerry was 39 and Shoshanna was 17 when they started dating.

An author ironically claimed on X (formerly known as Twitter) that he had gone to school with Shoshanna as he wrote: “When I was in high school 38-year-old Jerry Seinfeld was dating a girl in my year and he picked her up from class during 4th period and she got to skip Mr Solinski’s calculus exam (I got a 93/100)”.

The joke sparked a newfound interest in Jerry and Shoshanna’s relationship which had been quietly accepted back in the 1990s.

The comedian met the high school student in Central Park. After reportedly flirting and hitting it off, the pair seemingly started a relationship that lasted approximately four years.

Despite the significant age gap, Jerry’s association with a young student, while he was at the time the Emmy-winning star of the biggest show on television at the time, was a mere entertaining occurrence.

Following Shoshanna’s 18th birthday party, Jerry was teased on radio host Howard Stern's show.

"So, you sit in Central Park and have a candy bar on a string and pull it when the girls come?" Howard quipped.

#9 Aaliyah And R Kelly

One of the most infamous cases of a powerful and famous man dating a teenage girl involves convicted sex offender R. Kelly and the late Aaliyah.

The disgraced R’n’B star, then aged 27, reportedly silenced 15-year-old Aaliyah and her family through a non-disclosure agreement, following his marriage and subsequent annulment to her.

Allegations made in Lifetime’s “Surviving R. Kelly” docuseries centered around R. Kelly’s 2022 federal trial where the NDA was brought up in the courtroom as evidence. The One In A Million singer was listed as Jane Doe #1 in the trial.

“Surviving R. Kelly” included Aaliyah’s story as a victim of R. Kelly, after years of the media and music industry scandalizing her marriage to the criminal.

As Variety reported, Aaliyah’s debut album in 1994 was titled “Age Ain’t Nothing but a Number” and was recorded when she was 14 years old.

During this recording, R. Kelly was Aaliyah’s mentor. Rumors quickly circulated that there was a relationship between the teen music star and the nearly 30-year-old singer.

#10 Brad Pitt And Juliette Lewis

Heartthrob Brad Pitt has had a long career in the entertainment industry, with a dating history that is just as lengthy.

Amongst the numerous A-list celebrities Brad has dated, the actor was involved with actress Juliette Lewis.

When she was 16 years old, Juliette met a 26-year-old Brad while shooting the tele movie Too Young To Die.

Subsequently, both actors reportedly fell for each other.

"We met on a movie and started dating when it was over," Juliette told the Los Angeles Times in 1993. "I already liked him as an actor, plus you gotta respect somebody who’s in the same field as you."

#11 Melanie Griffith And Don Johnson

While on set for the 1973 movie The Harrad Experiment, 14-year-old Melanie Griffith met 22-year-old Don Johnson.

Thereafter, the two actors began dating before getting married in 1976. Melanie and Don’s marriage lasted six months.

Melanie’s mother, The Birds actress Tippi Hedren, reportedly allowed her to move in with Don when she was only 15.

Melanie told the Hollywood Reporter: “I thought he was the most beautiful person I’d ever seen.” 

Meanwhile, Don said back in 1975: “I was a little cocky at the time and didn’t talk to her mother for a couple of weeks.”

He continued: “Melanie and I became friends first, but then she picked me for something more.

“I was skeptical only because of her age, but she was a lot more woman than most of the girls I had been going out with.”

Don and Melanie reunited for a second marriage. Actress Dakota Johnson is their second child together.

#12 Luc Besson And Maïwenn Le Besco

According to The Washington Post, French filmmaker Luc Besson met the then-child actress Maïwenn Le Besco when she was 12 and he was 29.

Little did the media realize at that time that Luc and Maïwenn’s encounter inspired the 1994 award-winning movie, Léon.

In Luc’s movie, a 12-year-old Mathilda sees her family killed, as her neighbor Léon, who is a professional assassin, reluctantly takes her under his wing.

Luc and Maïwenn have claimed to have started seeing each other romantically when she turned 15. 

The My King actress went on to give birth to their daughter when she was just 16 and Luc was 33.

In an interview, Maïwenn said: “When Luc Besson did Léon, the story of a 13-year-old girl in love with an older man, it was very inspired by us since it was written while our story started.

“But no media made the link.”