The tenth season of Two and a Half Men premiered on CBS on September 27, , and Retrieved August 27, Jump up ^ Kondolojy, Amanda (August 27, ). "Actress Miley Cyrus to Guest Star on 'Two and a Half Men' This Fall". Missi is a character played by Miley Cyrus that appeared in Season 10 of Two and a Half Men. She is the ex-girlfriend and one of the first sexual partners of Jake Harper. In "You Do Know What The Lollipop Is For", Jake comes home on a weekend leave from the Army, meets Missi, and.