Mobile data services seem a promising revenue source for the stakeholders that have heavily invested on mobile communications infrastructures. However, in the Western world those services have not reached the mass markets yet. This chapter focuses on two markets that are representative of the European socio-economic environment, Greece and Denmark, with the aim to investigate and compare mobile data services use through the means of an online survey. We depict two user groups and observe their behaviors in both countries. The results indicate differences in locations and frequency of services use that can be attributed to specific socio-economic characteristics. However, certain similarities exist in the experience derived from mobile data service use since users believe that services cannot cater for their specific needs. We conclude by underlining the current challenges faced by mobile service providers in order to increase mobile data services use and summarizing user groups’ characteristics.