A Look at Wilmer Valderrama's (Long) Dating History

When: 1998

The former couple supposedly dated when they were teenagers, but only for about three months.

When: 1999

Rumor had it that Valderrama dated painter, Ariana Richards for about a month before the two went their separate ways.

When: 1999

Valderrama and "The Client List" actress reportedly started hooking up in late 1999, and while neither confirmed anything for years, the actor famously opened about their relationship in a risqué interview with Howard Stern. Hewitt stands firm on her denial of the alleged relationship.

When: 2000-2002

The two actors dated for two years and even after breaking up, remained friends and hang out often. Years following their breakup, Valderrama spoke to People, stating it took him four years to even give it a shot again after recovering from the relationship.

When: 2004

Valderrama and the "Freaky Friday" actress dated for two months when Lohan was just 18 before getting engaged, and calling it quits two months after.

When: 2005

Neither Simpson or Valderrama have confirmed rumors of their alleged, almost year-long relationship in 2005. However, if you listen to Simpson's song "Boyfriend" you'll get a sense that they did. Valderrama also told People the two were friends for years "before people were saying we were making out" even though he says they weren't.

When: 2009

Valderrama and Rihanna reportedly had a relationship for some time, but neither party ever commented on the rumors.

When: 2009

Supposedly, Lavigne started dating Valderrama shortly after filing for divorce from Sum 41's Deryck Whibley, but nothing was ever confirmed.

When: 2012 and 2016

Kelly and Valderrama were an item in 2012, and then spotted together again after the actor's breakup from Demi Lovato. The model set the record straight on Power 106 in 2016: "He's a good friend to me, and it's funny — he's not my ex. We are good friends, and we always have been. We're not exes!"

When: 2010-2016

The singer and Valderrama dated on and off for almost six years. Their 13-year-old age difference has recently been reexamined, especially through the lyrics of Lovato's song "29." In the main chorus, the singer says, "Finally 29, funny, just like you were at the time. Thought it was a teenage dream, just a fantasy, but was it yours or was it mine? Seventeen, 29."

Valderrama has finally settled down with his girlfriend-turned-fiancée, model Amanda Pacheco. The actor announced his engagement to Pacheco in an Instagram post, "It's just us now". The two lovebirds also welcomed a baby girl in February 2021.