Seneca’s De Beneficiis, the major gift-giving treatise of Paul’s day, manifests intriguing — yet to us culturally unnerving — ideals on gift exchange. Particularly discomforting, for a 21st century readership, is the nature and role of obligation. Like most Greek and Roman philosophers, Seneca affirms the presence of obligation as intrinsic to bestowing and returning gifts (e.g., 1.4.3; 2.11.5; 5.11.5). But does obligation play the same role in Paul’s vision of gift giving, specifically in his financial dealings with the Philippian community (Phil. 2:25-30; 4:10-20)? Two opposing views have emerged on the matter. One aligns Paul with Seneca, maintaining that his two-way friendship with the Philippians certainly entailed ‘mutual obligations’ (Peter Marshall). The other envisages a parting of ways with Seneca, insisting that Paul sought to eradicate the Greco-Roman conventions that had skewed their perception of Christian giving (G.W. Peterman). These polarized positions, however, are found lacking. The first view neglects the fact that Paul incorporates God into his monetary relationship with the Philippians, a three-way bond which, by necessity, reshapes the form of their mutual obligation. The second view, on the other hand, suffers from an anachronistic, post-Enlightenment mentality, which deems any kind of obligation a corruption of the inherent virtue within the gift. Therefore, by placing Seneca and Paul in conversation, this paper will attempt to develop a middle-ground position, one that factors God into the relational equation and recalculates the role of Christian obligation. This endeavour will not only draw out the striking similarities between these erudite thinkers but will also uncover the crucial point where they part ways — the essential role of the third party.