"Little Miss Obsessive" is a song recorded by American singer Ashlee Simpson for her third studio album, Bittersweet World (2008).

"Little Miss Obsessive" was produced by Jack Joseph Puig and Big Karl Berringer, with vocal production by Beanz.

"Little Miss Obsessive" is a pop rock power ballad that chronicles the "ostensibly aural dance" of a couple "who break up to make up – and like it".

[2] Simpson looked to herself for inspiration when writing "Little Miss Obsessive", which chronicles the "ostensibly aural dance" of a couple "who break up to make up – and like it".

[6] Sophie Bruce of BBC Music wrote that the song is the "standout success" of Bittersweet World and that is "deserves to take Ashlee to the forefront of female pop".

[10] Nick Levine of Digital Spy called "Little Miss Obsessive" a "decent enough tune, not a million miles away from 'Pieces of Me', but we can't see it reviving the album's fortunes".

[11] Alex Fletcher of Digital Spy wrote that despite a "surging power-pop chorus", "Little Miss Obsessive" lacks "the wow factor" required to "get people talking about Simpson's music again".

[7] Glenn Gamboa of Newsday called "Little Miss Obsessive" a "passable Pinkish pop" song, but stated that it isn't enough to keep Bittersweet World from "going sour".

[13] Stephen Thomas Erlewine of AllMusic called the song "quite awful", writing that exploring "the endless possibilities of the word 'over' in the chorus" is "a bit of a slog".