Ashlee Simpson » Dating

(August 31, 2014 - Present) Is Ashlee Simpson seeking the (musically) royal treatment? The pop star stepped out for a night out on the town in Hollywood on Monday, July 1, with Evan Ross, the son of legendary Motown singer Diana Ross, in tow -- and the two resurfaced again the next day for a daytime ... [more]

Vincent Piazza was dating Ashlee Simpson. They started dating in June 2011 and split up in November 2012 after dating for 17 months. Just a couple months after Ashlee Simpson was spotted holding hands with her estranged husband Pete Wentz, the singer has stepped out with a new man. Looking cozy in ... [more]

(May 17, 2008 - November 22, 2011) (divorced) (1 child) The two at first denied their relationship, before taking it very public and marrying on May 17, 2008. They have one child, Bronx Mowgli Wentz, born on November 20, 2008. In 2006, Simpson began a relationship with Fall Out Boy member Pete Wentz ... [more]

Braxton Olita was dating Ashlee Simpson. They started dating in October, 2005 and split up in July, 2006 after dating for 9 months. Simpson confirmed that she and Olita, a member of her backing band, were dating, telling Seventeen magazine that she and Olita and went on a 10-day vacation to Hawaii. [more]

The two were rumored to be together during 2005, with Simpson later writing the song "Boyfriend" about her time with Valderrama. Valderrama also claimed on Howard Stern`s show that he and Simpson were intimate, and that she was "loud in bed." They were photographed together, but never ... [more]

Tyler Hoechlin was dating Ashlee Simpson. They started dating in January 2004 and split up in March 2004 after dating for 2 months. [more]

Ryan Cabrera was dating Ashlee Simpson. They started dating in January 2004 and split up in August 2005 after dating for 19 months. The two pop-punk musicians were seen dating for much of the run of the MTV reality series The Ashlee Simpson Show, before parting ways. [more]

Back when Nick was dating Paris Hilton, it was rumored that he cheated on her with Ashlee Simpson. [more]

Gregory Smith was dating Ashlee Simpson. They started dating November 2003 and split up February 2004 after dating for 3 months. [more]

Ashlee Simpson met Carson Daly at entertainment lawyer Paul Schindler’s Central Park wedding in July of 2003. A month later they were spotted holding hands, kissing and whatnot at Joseph’s Cafe in Los Angeles. Didn't last long though. Carson Daly hooked up with Ashlee Simpson. They hooked ... [more]

Josh Henderson was dating Ashlee Simpson. They started dating in January, 2002 and split up in November, 2003 after dating for 22 months. The end of their relationship was captured on the premiere episode of the MTV reality series, The Ashlee Simpson Show. [more]