"Little Miss Obsessive" is a song recorded by American singer Ashlee Simpson for her third studio album, Bittersweet World (2008). It features uncredited guest vocals from Tom Higginson, the lead singer of the Plain White T's. The song was written by Simpson, Jim Beanz, Victor Valentine and Karl Berringer. "Little Miss Obsessive" was produced by Jack Joseph Puig and Berringer, with vocal production by Beanz. The song was released as the "first official single" from Bittersweet World on March 11, 2008, following the commercial disappointment of its predecessor, "Outta My Head (Ay Ya Ya)".

"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". Simpson looked to herself for inspiration when writing the song. Music critics were divided on "Little Miss Obsessive"; some critics felt the song was impressive, while others were critical of Simpson's vocals and the song's lyrics. The song only managed to chart on the national charts of Canada and the United States, where it peaked at 72 and 96, respectively.

"Little Miss Obsessive" was written by Ashlee Simpson, Jim Beanz, Victor Valentine and Karl Berringer. The song was produced by Jack Joseph Puig and Berringer. Simpson's vocals, which were produced by Beanz, were recorded at Archon Studios in Los Angeles and at Chalice Studios in Hollywood by Aris Achontis and Tal Herzberg, respectively. Tom Higginson, the lead singer of the Plain White T's, performed guest vocals in the song, as well as background vocals alongside Simpson and Mateo Laboriel, who also provided programming for the song. The guitar was played by Ray Brady, while Joey Kamani played the bass guitar and Abe Laboriel, Jr played the drums in the song. Dean Nelson engineered the song, while Puig mixed the song at Ocean Way Recording in Hollywood.

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