Valderrama and Lovato had an on-again, off-again relationship since meeting when she was 18. However, Lovato is far from the first young starlet to fall for the Hollywood lothario.
When Valderrama was 17, he had his first celebrity date with Richards, best known for being the little girl from Jurassic Park.
The That '70s Show co-stars allegedly dated while filming their hit sitcom. Now, Kunis is engaged to their other co-star Ashton Kutcher.
Valderrama is rumored to have briefly dated Hewitt in 1999. The Can't Hardly Wait star denies having any "steamy encounters" with the actor, but Valderrama told Howard Stern that JLH was "an eight" in bed.
Valderrama dated the the Venezuelan actress when she was on Roswellfrom 2000 to 2001.
Moore and Valderrama dated from 2001 to 2002. During his 2006 Howard Stern interview, the actor said he took Moore's virginity, but that it wasn't "like warm apple pie." Moore, however, said Valderrama's claim was untrue and "utterly tacky."
In 2004, Barton was at the height of her O.C.fame, which makes her decision to then date Valderrama that much more perplexing.
Lohan and Valderrama kept their relationship under wraps until LiLo's 18th birthday in 2004, since the Minority Report star was 24 at the time. But as soon as Lohan was of age, she moved into Valderrama's house. Unfortunately, the love didn't last. Lohan later revealed her single "Over" was inspired by Valderrama after he broke her heart.
Simpson and Valderrama were rumored to be an item in 2005, a relationship the actor pretty much confirmed when he told Howard Stern a year later that Simpson is a "screamer" in bed. Lindsay Lohan blamed Simpson for the end of her relationship with Valderrama, inspiring Simpson's hit single "Boyfriend."
After her divorce from Deryck Whibley, but before her relationships with Brody Jenner and Chad Kroeger, Lavigne reportedly dated Valderrama from 2009-2010. She clearly has a type.
During one of Valderrama's splits from Demi Lovato in 2012, the actor had a brief relationship with the FridayNight Lights alum.