Georgia's security alternatives in recent years have narrowed to a very concrete goal - NATO membership. This kind of choice seems to be logical for a small state. Nevertheless, security strategy, based on the key goal of alliance with stronger partner, may cause several problems. In the case of Georgia, security dilemmas are even more complicated. Unresolved problems with separatist regions were permanent key obstacles for Georgia to become reliable NATO candidate. The more Georgia was streaming towards NATO, the more relations with Russia deteriorated. The flashpoint of growing tension was the blitzkrieg of August 2008 between Georgia and Russia. Nevertheless the results of war may seem to provide the possibility for Georgia to resolve internal problems: however they failed to provide any guarantees for NATO membership. In this research paper the question - whether striving for NATO membership could guarantee Georgia's security - is analyzed. Also, the main obstacles for the realization of Georgia's security strategy and key dilemmas for NATO, in dealing with Georgia's case, are discussed.