Anna was born out of wedlock, although her parents were married in 1712 and she was later legitimized. Her earlier illegitimacy would pose great challenges for her marriage.
Anna grew up in the houses of Peter’s younger sister Natalia and Prince Alexander Menshikov. Although born illegitimate, she and her younger sister Elizabeth were awarded the titles of “princess” (tsarevna) on 6 March 1711 and “crown princess” (tsesarevna) on 23 December 1721.
Peter planned to marry his daughters to foreign princes in order to gain European allies for the Russian Empire. The two girls were educated with this aim in mind, learning literature, writing, embroidery, dancing and etiquette. Anna developed into an intelligent, well-read girl who spoke four foreign languages – French, German, Italian and Swedish.
Anna’s shyness were evident at an early age. One witness describes the amusing hitch that once occurred during the traditional exchanging of Easter kisses. When the duke of Holstein-Gottorp tried to kiss the fourteen-year-old Anna, she turned bright red in embarrassment, while her younger sister “immediately stuck out her little pink mouth for a kiss.”
Foreign visitors to the Russian court were struck by the uncommon beauty of Anna. The dark-eyed Anna looked more like her father and was considered more level-headed and intelligent than her younger sister, the fair-haired Elizabeth. A contemporary described Anna: “She was a beautiful soul in a beautiful body ... both in appearance and in manners, she was complete likeness, particularly in her character and mind ... set off by her kind heart.”
On 17 March 1721, Karl Friedrich arrived in Imperial Russia to get acquainted with his future wife and father-in-law. He aspired to use the marriage in order to ensure Russia's support for his plans of retrieving Schleswig from Denmark. He also entertained hopes of being backed up by Russia in his claims to the Swedish throne. Under the terms of the Treaty of Nystad Russia promised not to interfere in the internal affairs of Sweden, so his hopes proved ill-founded.
Another possible candidate as a husband was a grandson of Louis XIV of France and Madame de Montespan, Louis Duke of Orleans - the son of the Regent of France for the infant Louis XV of France. The marriage proposal was ignored due to a difference in style of address. Anna was addressed as Her Imperial Highness and Louis was as His Serene Highness.