Simonida was born in Constantinople c. 1294. In 1298, as a result of a Byzantine defeat, Emperor Andronikos II promised a marriage alliance to the Serbian ruler Milutin. Initially, Andronikos II intended to wed his sister Eudokia, the empress-dowager of Trebizond, but after she refused, Simonida was proposed instead.^[2] Church circles in Constantinople opposed the marriage, but the emperor was determined to push the deal through, and in late 1298 he sent his trusted minister Theodore Metochites to Serbia to conduct the negotiations. On his part, Milutin too was eager to accept, and even divorced his third wife, Ana Terter, the daughter of the Bulgarian tsar George Terter.^[2] Simonida was five years old, and Milutin was almost 50, was married three times, with adult children.^[3] The marriage was celebrated in Thessalonica in spring 1299, and the couple departed for Serbia in April.^[2] As a wedding present, Byzantines recognized Serbian rule north of the line Ohrid—Prilep—Štip.^[3]

According to some Byzantine sources Milutin did not wait until Simonida reached maturity before consummating their relationship, causing damage to her uterus and preventing her from ever carrying children.^[4] When this became known, Empress Irene, who was Andronikos II's second wife and had hoped to use the Serbian marriage to advance her own progeny, then offered Milutin to adopt one of her own sons as his heir.^[2]

Simonida showed great interest in theology at a rather young age and wanted to become a nun.^[3] After her mother Irene died in 1317, Simonida attended her funeral in Constantinople and decided not to return to Serbia after nearly a decade and a half of discussion.^[3] When Milutin's men came for her, she came to them in monastic habit. They were shocked, but her own half-brother Constantine Palaiologos took off her monastic habit and ordered her to take the civil dress. He then sent her to Serbia with Milutin's men, although she was reluctant to go.^[3] After Milutin threatened to start a war, Simonida came back to him.^[3] She was 22 years old.^[3] When Milutin fell ill, she was beside him all the time, much to the surprise of the rest of the court.^[3] Milutin died on 19 October 1321, and already on 29 October, Simonida returned to Constantinople, where she entered the monastery of Saint Andrew in Krisei as a nun.^[3]

There is very little information about her later life. It is known that she ordered a funeral song for her father's funeral. Simonida was last mentioned in historical documents in 1336 as an attendee at an assembly of civil and religious dignitaries, who prosecuted the conspirators against the government.^[3] She died some time after 1345.^[3]

Her beauty was well known, and she was known as a figure of purity and beauty in Serbian tradition. A fresco of her in Gračanica monastery is regarded as one of the most valuable frescoes in Serbian art.^[3] Unfortunately, the fresco is partly ruined, so that Simonida has no eyes.

She brought a large entourage to Serbia, and with her arrival, Serbia received a massive injection of Byzantine culture. Byzantine-style court ceremonials and dress were adopted, Byzantine functional and honorary titles appeared, court offices were renamed, and Byzantine administrative, fiscal and legal institutions were copied. Byzantinization was further expanded by Serbia's newly won populous Greek-speaking regions, in which Milutin retained all former Byzantine political, social and cultural activities. Strangely enough, none of this would have happened due to a near-death experience in 1303 during a small festival being held in Ras. A maid had nearly killed her by jumping off a known balcony but had failed to do so.^[5]

Milan Rakić wrote a lyric poem about her named Simonida,^[3] and Milutin Bojić wrote a psychological drama called Kraljeva Jesen ("King's autumn") about her.^[3][6] Asteroid 1675 Simonida discovered by Serbian astronomer Milorad B. Protić was named after her.^[3]

• Kassia
• Anna Komnene
• Jefimija
• Princess Milica of Serbia
• Saint Angelina of Serbia
• Mara Branković
• Olivera Despina
• Jelena Balšić
• Helen of Anjou
• Maria Angelina Doukaina Palaiologina
• Nicodemus of Tismana

• Đorđević, A. (2010). "The frescos Simonida in the Serbian poetry of the 20th century" (PDF). Baština (28): 65–74.