The relations between Stephen and Venice during the period between 1345 and 1350 show how easily an alliance between the Serbians and the Venetians might have been concluded. It was a critical time for Orkhan. Had Stephen Dushan, with the help of the Venetians, attacked Constantinople before 1350, the Osmanlis would have lost their goal. After his coronation, the ‘Roman emperor’ sent an embassy to Venice to secure the Senate’s aid for the definite purpose of acquiring Constantinople.[174] In 1347 the Senate, in response to a second overture, congratulated Stephen on having been crowned ‘emperor of Constantinople’, but regretted the impossibility of aiding him. There was a truce between Venice and the Byzantine Empire, and they were at that moment engaged in a war with Zara.[175] However, like typical merchants, they consented to sell arms to Stephen.[176] In January 1348 the Senate congratulated Stephen upon his exploits,[177] and later in the same year granted him three, then four, galleys.[178] This seems to be the extent of the help rendered by Venice to Stephen Dushan. The success of Stephen in subjugating Thessaly, and his progress farther south until, in 1349, the Serbian flags waved on the mainland opposite the Venetian castle of Ptelion in Euboea, alarmed the Venetians. The Senate complained of the piracy of the Serbians in the Aegaean, and tried to re-establish peace between Serbians and Greeks.[179] Stephen became more insistent and the Senate more reluctant. On April 13, 1350, the Senate considered several demands made upon them by an envoy of ‘Stephen Dushan, emperor of Serbia and Romania, despot of Arta and count of Wallachia’. Among them were Venetian citizenship for himself, his wife and his son, a conference with the Doge at Ragusa, and substantial aid for the attack upon Constantinople, ‘when he shall have conquered the ten parts of Romania outside of Constantinople.’[180] The chart of citizenship was accorded. But he was informed that the Doge never left Venice during his tenure of office, and that there was a treaty of friendship with the Byzantines which prevented Venice from joining in an attempt to capture the imperial city.[181] Convinced that he could expect no substantial assistance from Venice, Stephen planned to work the old trick of the Byzantine emperors. The Serbians were already excommunicated by the Greek Orthodox Church. Stephen negotiated with the Pope for the return of the Serbians into the Roman fold.[182]