"Pretty Handsome Awkward" is the second single from the Used's third studio album, Lies for the Liars. The song was released to US alternative radio on August 21, 2007. The single peaked at No. 37 on the US Alternative Airplay. It was rumored that the track was written about My Chemical Romance frontman Gerard Way, but Bert McCracken said that this is not true. In 2019, while performing at the Rockstar Disrupt Festival, Bert confirmed the song was about Way.

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