In the recent years the relationships of Ukraine and Moldova had positive dynamics, which nevertheless is clouded with certain problems, which can be figuratively marked with four "E"s: economy, energy, ecology, and ethnic minorities. The solution of these problems is possible, provided the intergovernmental dialogue continues and the international structures, foremost the EU, further support and mediate this process. Mutual interests of Ukraine and the Republic of Moldova in stability and security in the region became even more relevant and both sides support concordant policy towards Transnistrian settlement, as well as principles of borders inviolability and territorial integrity of Ukraine and the Republic of Moldova. However, further progress in this sphere largely depends on the results of the 2018 parliamentary elections in Moldova. The main problem of the bilateral relationships remains unpredictability and mutual lack of trust. This problem can be solved, provided there is political will of both sides as well as mediatory efforts of active civil society, which remains the main driver for democratization of both countries.