Critical response to Twentythree was largely positive though conservative, and she drew comparisons to fellow surfer Jack Johnson.

[4][5] USA Today gave the album four-and-a-half stars, saying that the "singer-songwriter's breathy wisp of a voice doesn't reveal much range, technically, dynamically or otherwise", but that she does "have a gentle charm that should allow this former competitive surfer to stay afloat under the pop radar.

"[6] Entertainment Weekly gave the album a B, calling it "husky, pleasant Introspection Lite.

"[4] People magazine said that "with her soothing folk-pop sounds and sweetly understated vocals, this San Diego singer-songwriter is poised to be the next Jewel", finally giving the album three stars.

[2] Christian Hoard with Rolling Stone commented that "Prettyman may not quite have found her voice, but on 'Twentythree' her nice-girl daydreams sound awfully sweet.