Online Peer-To-Peer lending has seen some growing media attention since its recent creation. Nonetheless, the systems which provide deal brokerage in this context have yet to be given significant consideration within the scientific community. This paper is part of a broader effort to setup a Peer-to-Peer lending community in Portugal. This work focuses on solving the infrastructural problem of combining investment offers from potential lenders with loan requests from potential borrowers. The combination process must strive for an optimal result, which pleases lenders and borrowers alike, despite their opposing agendas. Simultaneously the combination result should also benefit the platform’s business model, so as to keep it sustainable and profitable. Several optimization metaheuristics, powered by a constraint programming module, were applied to efficiently explore the problem’s solution space and to find optimal solutions. The results achieved with this approach show how metaheuristic-driven optimization can be successfully applied to Peer-to-Peer lending combination problems.