“Little Miss Obsessive” is the second single taken from Ashlee Simpson‘s third studio album, Bittersweet World, which is set to be released on April 22, 2008. “Little Miss Obsessive” features the Plain White T’s lead singer, Tom Higgenson, vocals. The song is a mid-tempo track that goes back to Ashlee’s musical style of the more pop/rock feel that she is mostly known for.