On May 5, Roadkill and James, with Mc Cool at ringside, lost a dark match on Smack Down against William Regal and Sylvan. on June 2, 2006, this time as a villainous character with a "sexy teacher" gimmick, pulling on her real life experiences as a teacher, and warning the Divas that she was "gonna take them to school".
On June 9, Mc Cool, Jillian Hall, Kristal and Ashley participated in a "Bikini Contest", which Massaro won.
While in OVW, she began managing the duo of Amish Roadkill and Kasey James.
On May 3, Roadkill and Kasey James, accompanied by Mc Cool, defeated The Untouchables (Deuce and Domino), who were accompanied by Cherry Pie.
In October, Mc Cool was legitimately hospitalized for over eight days after suffering a bad reaction to Ibuprofen after a CT scan.
On January 19, 2006, Trenesha Biggers and Angel Williams attacked Kristal Marshall during the intermission, but Tracy Tailor and Mc Cool made the save, and brawled with Biggers and Williams.
On November 25, Mc Cool helped Miss Jackie stretch and discussed the rumors of Charlie Haas cheating on her.
On July 15, Mc Cool and Victoria reached the finals of a Divas Mechanical Bull Riding Contest, which Mc Cool won.
On August 4, 2006, The Teacher's Pets, with Mc Cool at ringside, defeated Scotty 2 Hotty and Sho Funaki.
In August, the trio began feuding with Paul London and Brian Kendrick, and their valet Ashley, for the WWE Tag Team Championship.
In Summer 2004, the 24-year-old Mc Cool, participated in the Raw Diva Search contest, becoming one of the finalists, but placed 7th when she was eliminated on August 16; the winner of the contest was Christy Hemme.
However, Mc Cool and other Diva Search contestants were later signed by WWE.