In my article I try to examine the genesis of the Round Table negotiations in Poland and East Germany in 1989-1990 on the basis of the existing literature and archival sources. Despite the shared name “Round Table”, there were many significant differences concerning the genesis of the negotiations between the ruling communist parties and the opposition in the two countries. These differences can be observed on many levels, starting with the internal situation in both countries in the wake of 1989 – through their varied economic conditions, disproportionate political power of the opposition and dissident movements – up to different, though so close in time, political-historical context of both negotiations. Describing these historical asymmetries helps better understand spectacular changes of 1989 and their long lasting consequences.