The debatable expert and analytical assessments of the issues of foreign orientations of Ukraine in 2013 - 2014 have been analyzed in the article. The special attention was paid to materials of foreign policy expertise in the leading general political publications. The materials of mass media which related to problematic economical and political aspects of Ukrainian-Russian relations and the perspectives of signing the Association Agreement with the European Union were researched with consideration of assessments of the leading experts and publicists. The conclusion that the moderate and quite objective assessments of the sequence of events regarding signing the Association Agreement with the EU were provided by experts and columnists of political weeklies "Komentari", "Dzerkalo tyzhnya", "Fokus", and the daily newspaper "Den", is made. However, traditionally a more radical position regarding the "Eurasian vector" of foreign policy of Ukraine was taken by "Ukrayinsky tyzhden" periodical.