Massaro returned on January 7, 2008 to the Raw brand, winning a Lingerie Pillow Fight against Maria, Jillian Hall, Melina, and Mickie James. On the January 14 episode of "Raw", Massaro teamed up with Mickie James and Maria in a losing effort to the team of Beth Phoenix, Jillian Hall, and Melina in a 6 person-tag-team match. Massaro began a storyline with Maria and Santino Marella on the January 21, 2008 episode of "Raw", attempting to convince Maria to pose for "Playboy" but was interrupted by Marella. At the Royal Rumble pay-per-view, Massaro again attempted to convince Maria by telling her that Hugh Hefner wanted her to pose for "Playboy" before Maria could answer Marella interrupted and objected to the proposal. Massaro would then beat down Marella's surprise Big Dick Johnson when he attempted to perform a striptease. At the No Way Out pay-per-view, Massaro would appear with Maria in a segment at the Playboy Mansion. On the March 24, 2008, episode of "Raw", Massaro interfered in the match between Maria and Melina. After the match, Santino Marella came down to the ring, so Jerry "The King" Lawler (who was tired of Marella's actions over previous weeks) knocked Santino out of the ring. Which set up the six-person mixed-tag-team match, in which they lost to Marella, Melina and Phoenix. On March 30, 2008, Massaro replaced Candice Michelle, who was out with an injury, in the "Playboy Bunnymania" Lumberjack match at WrestleMania XXIV teaming up with Maria, losing to Beth Phoenix and Melina after the interference from Marella.