The paper analyses factors and conditions which determine the level of cooperation between Lithuania and Poland and which, according to their effect, are divided into driving forces and obstacles. The main driving forces are associated with the Euro-Atlantic objectives of both countries that affect the developmental trends and with the EU membership. They include different bilateral and multilateral agreements, participation in the institutions operating within the Baltic Sea macro-region, and in the pursued strategies, as well as the possibilities to benefit from the EU regional policy instruments. The obstacles for cooperation are associated with specific peculiarities of economic development of both countries. They cover the peripheral nature of Lithuanian economy as well as the inequality of economic potential of both countries. In addition, the "emotional charge", hindering the realization of the idea of strategic partnership, is also considered as an obstacle for further development of the discussed cooperation.