Recent research suggests that the “big five personality traits” influence the purchasing and usage preferences of mobile application. However, the impact of monetizing of applications and personality traits has so far been largely unattended. We have therefore extended our research to cover monetizing models of mobile applications. In this paper, we aim to enhance the understanding of the relationship between the “big five personality traits” and the usages and purchase intention of mobile applications in difference categories. Our initial data for the pilot study consists of 173 individuals, collected from smart device consumers who live in Bangkok, Thailand. Pearson’s correlation and multiple linear regressions were used to analyze the data. The initial results indicate that some personality traits are associated with the usages and intention to purchase mobile applications. It is highly possible to conclude from the data that conscientious persons placed more intention to use productive applications. Specifically, this personality trait has a positive relationship with utilities, education, business and maps and navigation. Neuroticism reported only significant relation with in-app purchase in utilities applications. Agreeableness showed no significance during our regressions analysis. The most widely used paid application among all traits is entertainment. The findings of this pilot study will serve as indicators for the direction of our planned future research in this field.