Adult Stars Who Dated Teenagers

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Some celebrities can’t seem to help themselves. Rather than date women closer to their own age, they go after young women and by young we mean really young. The celebrities we’re talking about have dated or married teenagers which, given how old some of these men are, is pretty disturbing. Maybe age is just a number, but there are plenty of women in Hollywood who are closer in age to these men. Here are 15 celebrities who dared to date teenagers!

15. Wilmer Valderrama 

Wilmer Valderrama has a reputation for liking ladies who are still in their teens. When he was 24, he began dating 17-year-old Lindsay Lohan. The couple kept their relationship under wraps until her 18th birthday. The “That 70s Show” star said that keeping their relationship secret made it more special. “We try to keep it more under wraps because it is a lot more meaningful that way,” he said. “At this point we don’t need all the free press.” It sounds like he knew that dating an underage girl wouldn’t look good, but he couldn’t help himself  – he likes them young!

14. Doug Hutchison

Doug Hutchison was 51-years-old when he married 16-year-old Courtney Stodden. She allegedly needed parental permission to tie the knot with her older lover, but that didn’t stop him from embarking on their controversial relationship. “We’re aware that our vast age difference is extremely controversial. But we’re very much in love and want to get the message out there that true love can be ageless,” Hutchison said. These two announced their separation in November 2013 after only two and a half years of marriage, so clearly it wasn’t true love.

13. Chad Michael Murray 

After his “One Tree Hill” co-star Sophia Bush divorced him, 24-year-old Chad Michael Murray began dating 17-year-old Kenzie Dalton who was an extra on the set of the show. The two dated for several years and became engaged while she was still a high school senior. Murray seemed like he was head over heels for his teenage love. “She is a little stunner. She is a sweetheart. She is my best friend and we have been together a long time,” the actor gushed to Us Weekly. After a seven-year engagement, the couple called it quits in 2013.

12. Kobe Bryant

Kobe and Vanessa Bryant met in 1999 when she was working as a backup dancer for a music video for Tha Eastsidaz. He was 21-years-old at the time, playing basketball for the Lakers, while she was only 17-years-old and a senior in high school. Shortly after meeting Kobe, she dropped out of high school. Apparently she received too much attention from her classmates over her relationship with the NBA star. These two are still together, even after numerous cheating scandals. They married in 2001 without a prenup, so chances are these two are in it for the long haul!

11. Milo Ventimiglia

Milo Ventimiglia began dating Hayden Panettiere, his co-star from “Heroes,” when he was 29 and she was 17. Apparently, Panettiere has a thing for older men. After she broke up with Ventimiglia, she started dating Ukranian heavyweight boxer Wladimir Klitschko, who is 13 years her senior. “It was never a case of me making a decision saying, “I want to date older men,” she said. “But I am drawn to people who make me up my game, who bring me up to their level. I want to be with somebody who is more worldly than me, somebody who can give me guidance and is completely secure and comfortable with who they are.”

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10. John Mayer 

John Mayer started dating Taylor Swift when she was only 19. He was 32 at the time and he ended up breaking her heart. After the breakup, she released a song called “Dear John.” In the song, she really let Mayer have it singing, “Dear John, I see it all now it was wrong/Don’t you think nineteen’s too young/To be played by your dark, twisted games/When I loved you so, I should’ve known.” When Mayer heard the song, he was anything but pleased. “It made me feel terrible. Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do,” he said.

9. Justin Gaston

Justin Gaston met Miley Cyrus when she was 15 and he was 20. The two met through her father Billy Ray and, while many fathers might loathe the idea of their young daughter dating an older guy, Billy Ray totally approved of Gaston. Back in 2008, he told Access Hollywood that he really liked him. “As a matter of fact, he went on a tour with me last week. We wrote some songs and just played a lot of music. He’s got a great heart,” Billy Ray added. The relationship didn’t last and, when it ended, the two of them bombarded Twitter with their sadness. “Tears are words the heart can’t express,” Cyrus wrote. Gaston tweeted, “How many tears are in there? They’ve gotta run out soon, right?” So melodramatic!

8. Joel Madden

In 2004, Joel Madden began a relationship with Hilary Duff when he was 25 and she was just 16 years old. They didn’t go public with their relationship until 2005, a year after they first began dating  The relationship lasted for three years with Duff being the one to end things. Apparently the age difference was causing problems.

7. Prince

Prince met Mayte Garcia when she was 16 years old and he was 31. It was backstage at one of his concerts in Barcelona and he was immediately taken by her and said, “There’s my future wife.” A romance didn’t begin immediately, however. It was when she was 19 and had been working with him for a few years that he instructed her to go on birth control that their relationship became sexual. The two got married in 1996 after a four-year courtship but divorced in 2000 after their only child was born with Pfeiffer syndrome and died six days after his birth.

Photo by Kevin Mazur/Getty Images

6. Paul Walker

Paul Walker didn’t just date one teenager girl when he was in his 20s and 30s, he dated two! The first teenage girl he dated was Aubrianna Atwell. She was reportedly 16 when they dated while he was 28. Then, at the time of his death, he was dating Jasmine Pilchard-Gosnell. Their relationship began when she was 16 and he was 33. She was closer in age to his daughter Meadow, who was 15 at the time.

5. Tyga

When Tyga was in his mid-twenties, he began dating a 16-year-old Kylie Jenner. It was when she was 17 that Amber Rose outed their relationship during an interview with Power 105.1. According to her, he left his fiancé and the mother of his child, Blac Chyna, to be with Kylie. The two only confirmed their relationship after the reality star’s 18th birthday, but then broke up a year later.

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4. Joaquin Phoenix 

Joaquin Phoenix – who is currently 39-years-old – is dating a woman 20 years his junior, a DJ named Allie Teilz. The “Her” actor is pretty private so no one is sure how long these two have been dating, but she looks young enough to be his daughter. She has allegedly been DJing since she was 16 and, despite not being old enough to drink, she is already a regular on the Hollywood and New York party scenes. “I had a complete double life and lied about my age, obviously, but I was really getting involved in the music world and starting to meet people. It wasn’t a good world for me being as young as I was,” Teilz said. Well, she is still pretty young!

3. Nick Lachey 

Nick Lachey is seven years older than his ex, Jessica Simpson. She was only 18 when they started dating whereas he was 25, which is a pretty big difference. Even though these two ended up getting married, they ended up getting divorced only three years after they tied the knot. Anyone who watched their MTV reality show “Newlyweds: Nick & Jessica,” saw it coming. Lachey quickly moved on to Vanessa Minnillo, who is the same age as his ex. Simpson moved on too. She is engaged to Eric Johnson who is only a year older than her.

2. Woody Allen

Woody Allen started dating Soon-Yi Previn when he was his mid 50s – she was only 19 at the time. He was dating her adoptive mother Mia Farrow when he began affair with the impressionable teen. He eventually left Farrow to be with Previn and, to this day, he doesn’t see anything wrong with their relationship. “What was the scandal? I fell in love with this girl, married her. We have been married for almost 15 years now. There was no scandal, but people refer to it all the time as a scandal and I kind of like that in way because when I go I would like to say I had one real juicy scandal in my life,” Allen said.

1. Jerry Seinfeld and Shoshanna Lonstein

Before he met his wife Jessica, Jerry Seinfeld – when he was 38 – dated a 17-year-old high school senior named Shoshanna Lonstein. Initially he lied about her age to Howard Stern but, when he visited his show again, Seinfeld admitted that Lonstein was young. “I didn’t realize she was so young,” he said. “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.” The relationship quickly became more serious. He called her “the most wonderful girl in the world.” Well, he got the girl part right.



Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.