Cradle RobbersTyga, Wilmer Valderrama, and More Adult Stars Who Dated Teenagers

Tyga and Kylie Jenner

Although rumors began circulating about their relationship a year prior, in 2015 Tyga finally confirmed he was dating the reality TV star. He was 25 at the time and she was just 17.

Linda Hogan and Charlie Hill

After her messy divorce from Hulk Hogan, Linda started dating a 19-year-old student who attended the same school as her children, Brooke and Nick. The two split in 2012.

Henry Cavill and Tara King

In 2016, the Man of Steel star had a brief relationship with 19-year-old college student Tara King.

"People say, 'Age is just a number,'" he said. "A lot of times it's not just a number. It's actually a real and true sign of someone's maturity. But in this case, she's fantastic."

Wilmer Valderrama and Demi Lovato

The two met when Demi was 17 and Wilmer was 30, and dated for six years. As far as when they officially started dating, the stars remain intentionally vague.

"He had some hesitations [initially]," Demi had said. "Once I got older, we could be together."

Milo Ventimiglia and Hayden Panettiere

The Heroes costars made headlines in 2007 when they went public with their relationship when he was 30 and she was 17.

"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."

Jerry Seinfeld and Shoshana Lonstein

In 1993, the comedian faced criticism for his relationship with a 17-year-old high school senior he picked up at Central Park.

"I didn’t realize she was so young,” Jerry said during an interview with Howard Stern. “This is the only girl I ever went out with who was that young."

Steven Bauer and Lyda Loudon

In 2014, the Scarface star began dating activist Lyda Loudon while he was 57 and she was 18.

“Lyda and I have faced criticism, but not from anyone interesting,” he said. “My family loves her and she loves them.”

Joel Madden and Hilary Duff

The two dated back in 2004 when Joel was 24 and Hilary was 16. In 2016, Hilary semi-revealed that she might have lost her virginity to him, too.

"I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing," she said.

Sam Taylor-Johnson and Aaron Taylor-Johnson

The Fifty Shades of Grey director started dating her now-husband when she was 42 and he was just 19.
“I’m an old soul and she’s a young soul," Aaron told The Sunday Independent at the time.

R.Kelly and Aaliyah

The two secretly married in 1994 when he was 27 and Aaliyah was just 15. The marriage certificate was falsified and had Aaliyah's age listed as 18.

“Well, because of Aaliyah's passing, as I've always said, out of respect for her mother who's sick and her father who's passed, I will never have that conversation with anyone," R.Kelly said about the wedding. "But I can tell you I loved her, I can tell you she loved me, we was very close."

Fergie and Justin Timberlake

Most don't know about this brief relationship that took place in 1996 during Justin's pre-fame days.

"He was 16 and I was 23," Fergie told Australia's Courier Mail. "It was before he got real heavy with Britney [Spears]."

Justin Gaston and Miley Cyrus

The two briefly dated in 2008 back when he was 20 and she was only 15. Although people were skeptical of the age difference, their relationship had the blessing of Miley's father, Billy Ray, who told Access Hollywood at the time that Justin had "a great heart."

Joaquin Phoenix and Allie Teilz

In 2013, the Her star briefly dated 19-year-old DJ Allie Teilz while he was 39.

NEXT: Joe Jonas, Henry Cavill and More Stars Who Admitted to Getting Aroused During On-Screen Sex Scenes