Wilmer Valderrama basically dated 12 of our biggest girl crushes from the '00s

by Arielle Tschinkel
Jul 21, 2016 at 4:00 p.m. ET

Valderrama dated Lovato on and off for about six years before they called it quits in June 2016, vowing to remain best friends.

1 /11: Ariana Richards

1/11 :Ariana Richards

Young love! These two briefly dated all the way back in 1999 and have never addressed their relationship publicly. She's best known for her role as the adorable Lex in Jurassic Park.

2 /11: Mila Kunis

2/11 :Mila Kunis

When Valderrama and Kunis were co-stars on That '70s Show, they had a rumored romance during filming, before Kunis was in a long-term relationship with Macaulay Culkin and her eventual marriage to mutual '70s Show co-star Ashton Kutcher.

3 /11: Jennifer Love Hewitt

3/11 :Jennifer Love Hewitt

These two dated briefly back in 1999, and he remarked to Howard Stern in 2006 that she was "an eight out of ten" in bed. Gag. For her part, Hewitt reportedly denied any "steamy encounters" with Valderrama.

4 /11: Majandra Delfino

4/11 :Majandra Delfino

Valderrama dated Delfino from 2000 to 2001.

5/11 :Mandy Moore

These friendly exes frequently reunite, and they dated from 2000 to 2002. In the same infamous Howard Stern interview, Valderrama claimed to have taken Moore's virginity, and said that it wasn't "like warm apple pie." Moore, however, said Valderrama's claim was untrue and "utterly tacky."

6 /11: Mischa Barton

6/11 :Mischa Barton

Valderrama reportedly dated Barton at the height of her fame back in 2004.

7/11 :Lindsay Lohan

This 2004 relationship was the source of several tabloid scandals, from the fact that she was not of legal age when they met to Lohan's feud with Ashlee Simpson after their breakup. Lohan admitted writing her song "Over" about their split, and it's rumored she considers him her first love.

8 /11: Ashlee Simpson

8/11 :Ashlee Simpson

Simpson and Valderrama dated in 2005, and he told Howard Stern in 2006 that she's a "screamer" in bed. Classy. His ex, Lohan, blamed Simpson for the end of her relationship with Valderrama, and Simpson reportedly retaliated with her song "Boyfriend." So much drama.

9 /11: Avril Lavigne

9/11 :Avril Lavigne

If it isn't already clear that Valderrama's "type" is '00s pop princess, he also reportedly dated Lavigne from 2009 to 2010, after her divorce from Sum 41 musician Deryck Whibley.

10 /11: Rihanna

10/11 :Rihanna

Neither party has ever confirmed this, but tabloids linked the two in a steamy hookup during a break from Lovato in 2009.

11 /11: Minka Kelly

11/11 :Minka Kelly

Kelly and Valderrama are rumored to have dated in 2012 on another break with Lovato, but Valderrama didn't technically confirm it, coyly saying, "Well, Minka Kelly and Wilmer Valderrama have been friends for a long time and that's all there is to it." OK, then.