Trouser Press wrote that "'Little Rosa', the album's highlight, is '60s-influenced jangle-pop genius."[2]
Entertainment Weekly opined that "too often singer Kay Hanley sounds like a petulant Juliana Hatfield on their soapy, overdramatic love songs."[7]
The New York Times compared the album to its predecessor, calling it "the same alt-rock in a different package". It said that, while Hanley's "bright, clear delivery often lifts Letters to Cleo above college-band status, her happiness can become wearing".[8]