The issue of psychosocial factors and concurrent conditions associated with AB is a relatively new approach in the study of Awake Bruxism (AB). In the present study a population of 84 dental students were assessed for probable AB with two modes of AB assessment: Single point self-report (SR) and ecological momentary assessment through a designated smartphone application (BA). The two assessment modes were compared with regard to their ability to phenotype subjects as far as the following psychosocial and behavioral variables are concerned: Gender; depression; somatization; oral behaviors; chronic pain and associated pain symptoms in the head, neck and scapula. Two-way ANOVA showed main effect of SR for the following variables: Chronic Pain Intensity score (F(1,49) = 6.441, p < 0.02), migraine/headache (F(1,81) = 7.396, p < 0.01), pain in neck (F(1,81) = 6.726, p < 0.05), pain in scapula (F(1,81) = 8.546, p < 0.005) and the oral behaviors of pushing the tongue forcefully against the teeth (F(1,81) = 5.222, p < 0.05) and inserting the tongue between the upper and lower teeth (F(1,81) = 5.344, p < 0.03). The effect of SR on the habit of chewing gum was borderline (F(1,81) = 3.369, p = 0.07). Main effect of BA was found for depression (F(1,81) = 6.049, p < 0.05), while the effect of BA on somatization was borderline (F(1,81) = 3.657, p = 0.059). An interaction between SR and BA groups could be observed for the behavior of biting, chewing or playing with the tongue, cheeks or lips (F(1,81) = 4.117, p < 0.05). The results suggest that a combination of a single-point self-report referring to the past 30 days, and an ecological momentary assessment supplying information about the actual timing of the report, can help us to better assess AB, as well as increase our ability to define the phenotype of subjects with AB as far as psychosocial and behavioral factors are concerned.