A historic chance that the capital city of Walachia got was its designation as the new capital of the union of the former Romanian Principalities – Moldavia and Walachia – that occurred during the winter of 1859. At the time, this union concentrated all the ambitions of the politicians of the moment in order to transform the widespread village that Bucharest was into a capital worthy of European recognition. Most of historic documents I have reviewed contain references to the European political and social context, including direct comparisons to the situations that were considered models to be followed. Although it is clear that setting Romanian Principalities on track to modernization, the promotion of French language and other western European values are, mainly, the results of the interaction with foreign army officers stationed in the principalities at the beginning of the 19th century, it is incomprehensible why the urban administrative practices of Russian Empire did not leave a clear mark on the evolution of Bucharest. Since Russian occupation of Bucharest occurred less than 25 years after Finland and Moldavian territories on the eastern banks of Prut river were annexed by the empire, it was natural to expect to observe some similarities in the administrative urban planning of the two gubernial headquarters and the administration and planning of Bucharest. Indeed, a brief investigation of the development of the two new gubernial capitals – Helsinki and Chișinău – reveals that these two towns could be considered twined since their designation as regional centers of administrative power. As a result, the two towns that became regional capitals within the same decade started their development in a very similar way from the urban planning point of view, based on a grid plan applied next to the small medieval nucleus. It is an interesting process if considering that the administrative assimilation by the empire of the two regions and nations was slightly different. The urban plan formula used in Chișinău and Helsinki was already a well established pattern set up a century before by Peter the Great when he erected his new capital in Sankt Petersburg starting from empty land. What Peter the Great applied for building Sankt Petersburg (even if never completed as such) became the developing rule for every new or extended towns in the expanding empire and in the administrative modernization effort of the later Catherine the Great. How come that in Bucharest’s case, a capital city of united provinces long time desired for Russian Empire as key to control the Danube and the Black Sea, the urban scheme had no effect even if Governor Kiseleff made such a great impact on the rest of the administrative system in a period so close in time to the expansion to Finland and part of Moldavia? A possible answer might be that 6 years of occupation were not enough anyway for such a process even if this kind of objective was intended and traced into a conceptual urban sketch. Another possible answer would be related to the traditional Romanian conservatism that was clear including through the public revolt and revolutionary movement of 1848 when one of these expressions was exactly the public burning of the so called “Regulament Organic”, the embryo of a constitutional society. At the time, Paris was the beacon and the source of social aspirations and therefore became the source of a real administrative revolution based on the seeds planted two decades before by Russians through Pavel Kiseleff. Of course, more important, the size of Bucharest of that time, making this town to be considered one huge village, in fact a collection of villages, is a reason for the difficulty of rationalizing its plan introducing grid templates. Even if there are substantial differences, urban developments of Chișinău and Bucharest deserve more attention in comparing them since present days might show that Chișinău grew as well into a wide area as a collection of former villages. This might seem as closing a circle in time so Bucharest experiences should be understood in order to substantiate the choices among future options in solving present challenges of Chișinău for not making the same mistakes. And knowing the common features in the early years of Helsinki and Chișinău might bring the municipalities closer together as, beyond the inherent different mentalities of the inhabitants of the two towns, Helsinki could teach some of its pragmatism to what it could be its first official “twin city”.