With the advent of the ever increasing, persisting, developing and becoming more complex migration phenomenon, labour migration in particular, its widening and thriving consequences are also notably uncovering. Transnational parenting, being one of the products of migration, has been one of the concentrations of the current studies related to global migration in which this research has also rooted its inspiration. This qualitative research which employed grounded theory approach explored and delved on the lived and distinct transnational parenting experiences of eight Filipino fathers in Portugal who have children left-behind in the Philippines. The primary aims and objectives, which are also the strengths of this study, were to empirically discover a facet of transnational parenting phenomenon involving Filipino fathers and attempt to cull out potential theoretical perspectives or model in keeping with the prescriptions of the used research approach. In the final analysis, seven themes emerged highlighting the realities of these fathers’ transnational parenting experiences concerning their 1) perceptions about the meaning of parenting, 2) deep desire to support the needs of their children back home and help them prepare for their future, 3) general desire for better living condition, 4) performed long-distance parenting (LDP) roles, 5) benefits of communication technology, 6) ways and means of overcoming the challenges accompanied in performing LDP roles and lastly, 7) preference for closer proximity type of parenting. The connections found on these empirical evidences provided an opportunity to frame a theoretical model which the researcher coined, “The laddering forces on transnational parenting” that is unique to the experiences of the participants but can be a promising reference to help understand similar cases in the area of transnational parenting markedly among Filipino parents across the globe. One of the highlights found in the model is one paradox that in spite that the emerged themes tend to increase possibility of strengthening adherence to performing transnational parenting among Filipino fathers, it has been articulated as well that they still have preference for closer proximity mode of parenting (in which they are in close physical contact with their children while doing their parenting roles) on two main factors; Filipino culture/family values (a given factor) and longing for better economic/living condition in general (longed factor) notwithstanding the location of performing parenting roles.