"Boyfriend" debuted on the "Billboard" Hot 100 in September at #71 thanks in part to its strong downloads, and in its second week of release, it climbed from #71 to #24 (also rising from #32 to #7 on the Hot Digital Songs chart), making it Simpson's second biggest hit on the Hot 100 to date ("Pieces of Me" reached #5 on the Hot 100 in 2004). Though it continued to drop for a couple of weeks after reaching #24, it later rebounded on the charts and hit a new peak of #19, making "Boyfriend" Simpson's second top twenty U.S. hit. In its 17th week on the chart, after falling out of the top 50, "Boyfriend" rebounded from #75 to #34; this put it ahead of "L.O.V.E.", Simpson's second "I Am Me" single, which was at #36 and also rising on the Hot 100.