Thick and coarse hair, as typically found among the Japanese population, frequently lacks softness that consumers are acutely aware of. Such poor feeling is accentuated by daily grooming, weathering, and chemical treatments, in particular, which can cause changes in the hair shape and the creation of frizzy or irregularly shaped hair. Existing technologies to improve the soft feel of hair, though effective, usually concentrate on the surface of the fiber and often leave the hair feeling either overconditioned or sometimes even sticky from product buildup. Hair softness is said to be governed by a number of factors, but primarily hair diameter and surface condition. In this study, we have also identified hair alignment as playing a critical role in hair softness. In addition, by studying how Japanese women perceive hair softness when touching their hair, we have identified that the strain on the hair fiber associated with these manipulations is far smaller than previously considered. With these factors in mind, we have studied the mechanisms behind a new softening technology containing glycylglycine (GG). It has been found that treatment with GG can give a tangible feeling of hair softness by dramatically improving alignment in unruly hair and by lowering the modulus of the fiber. Moreover, using the atomic force microscope, it has been revealed that the properties of the cell membrane complex of the hair cortex may be modified after GG treatment; the role of this additive in modifying the internal properties of the hair to create softness will thus be discussed.