As a result of the relationship, Goldstein appeared in a 2005 episode of Punk'd, where Richie was the subject of a practical joke, and that same year he featured in an episode of The Simple Life, a reality TV show focusing on Richie and Paris Hilton. Goldstein and Richie announced their engagement in February 2005, but broke up in late 2006. Goldstein was a guest DJ on an episode of The Ellen DeGeneres Show in May 2006. He was an avid sneakerhead, owning more than 1,000 pairs of sneakers by 2007. This led to him being offered a cameo as himself purchasing a pair in the 2006 TV series Entourage episode "What About Bob?". That same year, Goldstein also began working at Caesars Palace, becoming the resident DJ of their nightclub Pure. He was contracted to the club for the year for $1 million, which was considered to be an unprecedented amount for a DJ at the time. By 2007, he was also being paid between $10,000 and $25,000 per event as a solo DJ. Goldstein scratched on albums for Papa Roach, Will Smith and Babyface. He played at private events for celebrities including Jennifer Lopez, Ben Stiller and Leonardo DiCaprio. Goldstein dated singer Mandy Moore for two months in 2007 and remained close friends with her after separating. Later in 2007, he was romantically involved with model Jessica Stam.