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When Princess Sophie of Anhalt-Zerbst was betrothed to Peter III of Russia in 1744, Chernyshev was chosen by Empress Elizabeth of Russia as one of three nobles to join the princess' personal court as a gentleman of the chamber. In 1745, Chernyshev's mother begged Empress Elizabeth to send her son away because she feared his infatuation with the Grand Duchess Catherine Alekseievna of Russia; Chernyshev was given a diplomatic assignment. When he returned to Saint Petersburg six years later, Chernyshev began actively courting the then-grand duchess: flattering Catherine, sending love letters, and finding occasion to recreate with the royal.