Adult Celebrities Who Dated Teenagers

Celebrities have no shortage of rich, beautiful, of-age partners to woo, yet some of them still get entangled with partners they can't legally take into bars. There are different shades of sketchy to this: A 21-year-old dating someone who's 18 or 19 is a lot different than a 27-year-old dating a high school freshman or a man who's edging 40 hooking up with a girl who's busy thinking about her prom dress.

Psychologists explained to Bravo that there are a few reasons adults date teenagers. Older partners may want to deny their own mortality by dating a younger person, and humans are reportedly programmed to seek out young, fertile mates. "For others, it may be a longing or need to be doted upon and appreciated for their stature and significance," psychotherapist Camilla Mager told the site. "And for others, on occasion, I do think genuine love can emerge." Whatever the reason, these grown-up stars dated teens.

David Bowie and Jimmy Page allegedly dated the same groupie

Groupie Lori Mattix alleges that music icon David Bowie took her virginity when she was 14 or 15 and he was in his mid-twenties on his Spiders From Mars tour. Mattix told Thrillist about her alleged first time with Bowie, and she also claimed Led Zeppelin guitarist Jimmy Page (then in his late twenties) was "one of the great loves of [her] life" when she was a teen

"At that point, I was 15 and totally in love with this man ... It became so serious that Jimmy asked my mom for permission to be with me," she said. "Looking back, he had to be afraid of getting sued for being with such a young girl, so maybe he thought it would be better if he cleared it with my mother and told her he was in love with me."

Beyonce caught Jay-Z's eye when she was barely legal

According to Us Weekly, in The Carters' song "713," Jay-Z says he first met Beyoncé at MTV's Spring Break in Cancun in 2000. That means Beyoncé would have still been a teen while Jay-Z was already in his thirties at the time.

Queen Bey also talked about their meet-cute with Seventeen (via PopSugar) in 2008. "I was 18 when we first met, 19 when we first started dating. There was no rush — no one expected me to run off and get married. I really don't believe that you will love the same thing when you're 20 as you do at 30. So that was my rule: Before the age of 25, I would never get married. I feel like you have to get to know yourself ... before you can share that with someone else." The pair wed in an intimate, hush-hush ceremony on April, 4, 2008. She was 26, so she apparently took her own advice seriously.

Chad Michael Murray wooed with a high school student

Then-25-year-old Chad Michael Murray began dating then-17-year-old One Tree Hill extra Kenzie Dalton before his annulment to One Tree Hill co-star Sophia Bush was finalized. Dalton, who plays a cheerleader on the CW staple, and Murray got engaged when she was an 18-year-old high school senior, according to the Daily Mail. "She is a little stunner," Murray told Us Weekly in 2012. "She is a sweetheart. She is my best friend and we have been together a long time." 

They split in 2013, after a seven-year engagement. Murray rebounded with Left Behind co-star Nicky Whelan, who was actually about a year older than him, Us Weekly reported. Eventually, the actor settled down and married actress Sarah Roemer in 2015, when they were both in their early thirties.

R. Kelly has been accused of crimes involving minors

The docuseries Surviving R. Kelly (via People) claims R&B star R. Kelly had an inappropriate relationship with his protégé, Aaliyah, when she was 15 and he was 27. Kelly's former backup singer alleged that she witnessed him having a sexual relationship with Aaliyah on a tour bus. "I was in the room when they got married. I'm not proud of that," the former dancer claims. "I had papers forged for them when Aaliyah was underaged. It was just a quick little ceremony, she didn't have on a white dress, he didn't have on a tux ... She looked worried and scared."

Kelly is accused of sexually abusing several other girls in the documentary. He has denied the allegations. Aaliyah's mother has reportedly claimed the dancer is lying, though Aaliyah's boyfriend at the time of her death, music producer Dame Dash, has alleged that Kelly raped her.

Milo Ventimiglia learned from his experience

Milo Ventimiglia dated Heroes co-star Hayden Panettiere when he was 31 and she was 19, according to the Daily Mail. The pair reportedly split in 2009, due in part to the age difference. "It was a lifestyle conflict," a source dished to Us Weekly (via the Daily Mail). "They were in very different places. [Hayden] is young. She likes to go out in the Hollywood scene and that's not his style."

Ventimiglia talked candidly about dating his much younger co-star with Mr. Porter. "Never do it again. There are things that happen to you in your life that shape who you are. Everything I've been through from jobs to friendships to partnerships, everything has built me to who I am. You learn from it. You learn a better way of doing things. It wasn't until my mid to late twenties that the job wears on you, relationships wear on you."

Fergie says she fooled around with a 16-year-old JT

Before Fergie and Justin Timberlake collaborated on "Where is the Love," they were an item — and depending on what state they were in at the time, Timberlake may not have been legal. Fergie talked about her fling with Cosmopolitan in 2006: "One my good friends was dating JC Chasez, and so we'd all hang out with N'SYNC. 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." 

Fergie, who sang in girl group Wild Orchid at the time, later told the Courier Mail (via Us Weekly) that those smooch sessions went down when he was 16 to her 23. When that scandalous topic cropped up on Watch What Happens Live With Andy Cohen in 2017, Fergie responded, "It wasn't all that serious. Pass! Can I plead the fifth?"

Steven Tyler became his underage girlfriend's guardian

When Aerosmith frontman Steven Tyler allegedly began hooking up with Julia Holcomb in November 1973, she was 16 to his 25. In an essay for the Life Site, she said her mother relinquished guardianship to the rock star, writing, "A sense of vulnerability came over me, knowing that I was his ward, but we were not married. He had not expressed his intentions of a long-term relationship with me. He had mentioned that he wanted guardianship papers so I could travel across state lines when he was on tour."

Holcomb alleges that Tyler told her mom he needed her to sign the forms so he could enroll her in school. She also claims Tyler pressured her into having an abortion when she was five months pregnant with his child, a son. Both Holcomb and Tyler reportedly regret that decision. According to the book Walk this Way (via LifeNews), Tyler said witnessing the procedure "devastated" him. "In my mind, I'm going, Jesus, what have I done?"

Wanya Morris and Brandy had to hide their love

Brandy was 16 when she reportedly started dating 21-year-old Boyz II Men crooner Wanya Morris. They kept their relationship quiet due to the age difference and to protect her clean image. "Immediately everything was about my career," she lamented on VH1's Behind the Music (via Contact Music). "What are you teaching young girls? Do they fall in love at a young age? Is that wrong? Is that a sin? It just made me feel like I was all by myself and that whatever I'm feeling personally is going to have to be put to the side."

The stress of keeping their love under wraps put a ton of pressure on the young couple. Morris reportedly left Brandy for another girl, one who he ostensibly wouldn't have to hide from the world. "It felt like somebody had just completely taken my heart out of my body and just crushed it," Brandy said.

Jerry Seinfeld dated a high schooler when he was pushing 40

When Seinfeld was still on the air in 1993, a 38-year-old Jerry Seinfeld met 17-year-old high school student Shoshanna Lonstein in Central Park and they exchanged numbers, reported People. In fairness, she turned 18 shortly after they met, but even shock jock Howard Stern called Seinfeld out on it, to which the comedian replied, "I didn't realize she was so young. This is the only girl I ever went out with who was that young. I wasn't dating her. We just went to a restaurant, and that was it." 

Seinfeld talked about the relationship with People in 1994. "I am not an idiot. Shoshanna is a person, not an age. She is extremely bright. She's funny, sharp, very alert. We just get along. You can hear the click ... My interest in her is very proper." According to the New York Post (via E! News), they dated for five years and split in 1998, when she was 21 to his 42. 

Woody Allen reportedly dated teens in his forties

Acclaimed moviemaker Woody Allen dated actress Mia Farrow from 1980 to 1992. They split after Farrow found nude photos of her adopted daughter, Soon-Yi Previn, in Allen's possession. Allen excused his behavior to Time: "There's no downside to it. The only thing unusual is that she's Mia's daughter. But she's an adopted daughter and a grown woman. I could have met her at a party or something." Previn's age when she and Woody began getting involved is unclear; Vanity Fair estimates she was between 19 and 21 — about 35 years his junior. 

Regardless, this wasn't the only time Allen dated a much younger woman. Actress Babi Christina Engelhardt alleged in The Hollywood Reporter that she began a years-long love affair with Allen when she was 16 and he was 41. When Allen was 42, he reportedly romanced 17-year-old actress and high school senior Stacey Nelkin, and that relationship "is said to have partly inspired the one between Allen and Mariel Hemingway in 1979's Manhattan," reported The Wrap.

Elvis got older, but his love interests stayed the same age

Priscilla Beaulieu was only 14 years old when she met 24-year-old Elvis Presley at a party while the "Hound Dog" singer was in the army and stationed in Germany. "Instantly smitten, he began dating the stunning teen; the couple kept in touch after he returned home, with Beaulieu occasionally visiting her beau in the USA," reported USA Today. "In 1963, she moved there for good — under strict conditions put forward by her parents, who expected that Elvis would ultimately marry her." He did in 1967. They welcomed daughter Lisa Marie Presley in 1968 and divorced in 1973.

According to the book Elvis Presley: A Southern Life (via Broadly), Presley had dated teenagers before, and post-Priscilla, "The King" reportedly dated 15-year-old Reeca Smith. She told Express, "I was 14 and he was turning 40. He wanted to take me to Las Vegas and Nashville but my parents refused to let me go."

Wilmer Valderrama had a type

Actress Mandy Moore told People that she and Wilmer Valderrama reportedly met on a photo shoot in 2000, when she was 15. She said they started dating when she was 16 or 17 (He's about four years her senior.) The classy That '70s Show star even boasted to Howard Stern about taking Moore's virginity, which she denied. 

In 2004, a 24-year-old Valderrama reportedly went public with an 18-year-old Lindsay Lohan — as in she moved into his house. He also spoke about Lohan's private parts in great detail on Stern's show.

Pop star Demi Lovato said she fell head over heels for Valderrama in 2010, when she was 17 and he was 29. "When I turned 18 we started dating. I think it was love at first sight..." she says in her documentary, Simply Complicated (via People). They split in 2016, after nearly six years together.  

The Weeknd pursued Bella Hadid

The Weeknd (real name Abel Tesfaye) and model Bella Hadid reportedly began dating in 2015, when when she was 18 and he was 25. The "Can't Feel My Face" crooner realizes the timing was important, telling Rolling Stone the relationship "just kind of fell into my lap." He said, "If this had happened two years ago — well ... she couldn't."

Testfaye revealed that he initially asked Hadid to appear in the artwork for his 2015 album Beauty Behind the Madness, but she passed. "I was like, 'All right, cool — we can meet up face-to-face.'" Their on-again-off-again romance has been making headlines ever since. In December 2018, she told Vogue that he's the "most beautiful person" she knows.

Paul Walker had a controversial pattern

Before The Fast and the Furious franchise star Paul Walker's untimely death in 2013, he reportedly had an often-overlooked pattern of dating teenage girls — some of whom were close in age to his own daughter, Meadow. In fact, critics have slammed the I Am Paul Walker documentary that was released after his death because it "seeks to immortalize the actor's life and his accomplishments" but "ignores the major controversy surrounding his relationships with underage girls," reported Jalopnik.

According to the Daily Mail, Walker's girlfriend at the time of his fatal car crash was Jasmine Pilchard-Gosnell, who'd "been dating Walker since 2006 when she was just 16 and he was 33." The tab reported that Pilchard-Gosnell "was supposedly beginning to become the step-mother to Walker's daughter," who was about eight years younger than her father's beau.

Doug Hutchison married a 16-year-old

Actor Doug Hutchison married 16-year-old Courtney Stodden in 2011, when he was 51 years old. The dysfunctional pair became famous as reality stars, appearing on Dr. Drew's Lifechangers, Celebrity Big Brother, and Couples Therapy. A 23-year-old Stodden filed for divorce from Hutchison in 2018, reported People"I feel like I really didn't get a chance to do a lot of things a normal [teenage] girl goes through and experiences," she said. "'s kind of like a split world where I feel like I'm, you know, 57, like his age, but then I feel like I'm 7, you know, because I've missed out on a lot of things."

Stodden's mother, Krista Keller — who had to sign off on the marriage because her daughter was a minor — eventually came to the same conclusion. "I don't think it was a very healthy [relationship]," she told Radar Online. "...It was very unnatural for her to be with someone that much older and I think the problems played themselves out."

Tyga may have 'got in early' with Kylie Jenner

Tyga and Kylie Jenner didn't go public with their relationship until she was 18, but Kanye West suspected the spark somewhat sooner. Rumors circulated that the rapper and the reality star were an item when she was 17 to his 25. "I think he got in early," West told The Breakfast Club (via E! News) in February 2015. "I think he was smart." 

Tyga denied dating Jenner when she was a minor, though he did dish about his romance after splitting from Jenner in 2017. "I mean, we started off as friends, and then we got into a relationship," he told The Breakfast Club (via E! News). "When you're with anybody that first year, it's magic and then after that you start realizing a bunch of s**t ... she's younger than me and she's dealing with perception. I'm older so I can deal with perception. But for her, growing up how she grew up, image and perception was everything."

Henry Cavill tries the shoe on the other foot

Henry Cavill dated 19-year-old college student Tara King in 2015 and 2016 — when he was in his thirties. At least he realized it was unusual. He told Elle in February 2016 that it was a "natural reaction" to question their age difference, but added, "People say age is just a number. It's actually real and true sign of someone's maturity. But in this case, she's fantastic." The actor noted that he dated a thirty-something when he was 19 too. When asked what he learned from his own teenage love story, Cavill quipped, "Things that I can't mention in an article."

Needless to say, King and Cavill's relationship came and went faster than a speeding bullet. He allegedly moved up, up, and away just months after that interview was published. "She was in too deep and he didn't want anything too serious," a source told Us Weekly. "He has a lot going on right now. They'll remain good friends, but it just wasn't meant to be..."

Taylor Swift dated a high school kid

In 2012, 22-year-old Taylor Swift caused a tabloid ruckus when she dated Conor Kennedy. Right after he celebrated his 18th birthday, the two began traipsing about in public together, according to E! News. Kennedy was still in high school at the time, but Swift described him as a "grown man" in an October 2012 interview with Rolling Stone. "The way I look at love is you have to follow it, and fall hard, if you fall hard. You have to forget about what everyone else thinks. It has to be an us-against-the-world mentality. You have to make it work by prioritizing it, and by falling in love really fast, without thinking too hard. If I think too hard about a relationship I'll talk myself out of it."

Swift also caused a stir in the rumor mill when she allegedly bought a house (via her management company) near her teenage love interest. That house was reportedly flipped for a profit after the summer fling sputtered.