Hola Kyle,
I would have to agree with Hannah above, we would need a bit more information to be able to properly assist you with this question. I am though including a screen shot of the attribute table, reflecting the properties of the �??Comments�?� field for your review of Riverside.mxd. In reviewing this mxd, hopefully this will assist you in setting up your field within ArcMap in the same manner, and this will reflect within ArcPad. Gracias, Kyle!