Shady Details About NCIS Star Wilmer Valderrama's Dating History

When fans were introduced to Wilmer Valderrama on "That '70s Show," the then-18-year-old hadn't been cast in a heartthrob role  but he quickly became one of Hollywood's most prolific lotharios. Songs were even written about him. On "Watch What Happens Live," Ashlee Simpson confessed that her mid-aughts hit "Boyfriend" served as a message to another teen pop star who dated Valderrama, Lindsay Lohan. And on "The Ellen DeGeneres Show," Lohan confirmed that her song "Over" is about her split from Valderrama, revealing that she recorded it within earshot of her ex in the house they once shared.

Valderrama's relationship history includes a number of successful young starlets, and one acquaintance from his clubbing days told the New York Post that this is no coincidence; the "NCIS" star purportedly sought them out. "Wilmer comes off as the elder Hollywood statesman to the young girl who's kind of freaked out by all of it," said the insider. Valderrama also knows exactly how to make a gal feel special once his target is acquired. In lieu of an individualized gift, he presents her with the same love token he gives all of his girlfriends. "When he likes someone a lot, he gives them a black sweatband from Chrome Hearts," said a pal of the actor. "It means that you're his girlfriend, that you can hang out in his crew." How romantic.

It took many years, but one of Wilderrama's younger exes seemingly called him out for finding their age discrepancy totally acceptable.

Maybe it wasn't the best move for Wilmer Valderrama to star in a movie titled "Unaccompanied Minors." On "The Howard Stern Show," Mandy Moore said she was 15 when she first met Valderrama, and she started dating him at age 16. "Never French kissed a boy. He was my first real, true boyfriend," she shared. When their relationship began, Valderrama would have been 20 years old. He's also six years older than Lindsay Lohan, who started spending time with the actor when she was 17, per People.

But the age difference between Valderrama and his ex Demi Lovato is more extreme; he was 29 and she was 18 at the beginning of their on-again, off-again relationship. So, when Lovato released a song titled "29" in 2022, the assumption was that it was about Valderrama. "Petal on the vine, too young to drink wine / Just five years a bleeder, student and a teacher," Lovato sings. "Far from innocent, what the f***'s consent? Numbers told you not to, but that didn't stop you." 

While discussing "29" during an Apple Music interview, Lovato wouldn't outright confirm that it was inspired by Valderrama, but she said, "I feel like the song says it all." She also revealed that turning 29 herself made her reflect back on her teenage relationship and allowed her to view it in a different light. Per The Los Angeles Times, the track sparked a discussion about grooming on TikTok.

Demi Lovato can thank her lucky stars that she was just 13 years old when Wilmer Valderrama gave a master class in the art of oversharing about his love life during a 2006 appearance on "The Howard Stern Show." While boasting about his sexual conquests, Valderrama shared intimate details about Lindsay Lohan. He also claimed that he took Mandy Moore's virginity and compared her to a baked good. (We're guessing he's a big "American Pie" fan.) But Moore later told Elle that Valderrama was telling a tall tale, saying that his remarks were "utterly tacky."

When she appeared on "The Howard Stern Show" in 2018, Moore said that she and Valderrama had remained in touch after their breakup, so she confronted him about his dishonesty. "That's why I was so shocked by it, because not only was it a fib, but it was so unlike him," she said. According to Moore, they patched things up and were still on friendly terms.

Valderrama had also claimed that he slept with "9-1-1" star Jennifer Love Hewitt. "I was told that we had all these very steamy encounters and I was like, 'Really! Well, I would have loved to have been there,'" said Hewitt of the boast, according to Fox News. Valderrama eventually stopped pursuing relationships with big-name celebs and got engaged in 2020. His fiancée, model Amanda Pacheco, is 11 years his junior... and was almost 29 when Valderrama popped the question.