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<blockquote>I hate the rich man moaning as if he were poor.</blockquote>
She was born between 805 and 810 in Constantinople into an wealthy family <ref>Touliatos, Grove online.</ref> and grew to be exceptionally beautiful and intelligent. Three Byzantine chroniclers, [[Symeon Metaphrastes]], [[George the Monk]] (a.k.a. George the Sinner) and [[Leo the Grammarian]], claim that she was a participant in the "bride show" <ref> The Bride show was the means by which Byzantine princes/emperors sometimes chose a bride, by giving a golden apple to his choice</ref> organized for the young bachelor [[Theophilos the Iconoclast]] by his stepmother, the Empress Dowager Euphrosyne. Smitten by Kassia's beauty, the young emperor approached her and said: "''Through a woman [came forth] the baser [things]''", referring to the sin and suffering coming as a result of Eve's transgression. Kassia promptly responded by saying: "''And through a woman [came forth] the better [things]''", referring to the hope of salvation resulting from the Incarnation of Christ through the [[Theotokos]]. According to tradition, the dialogue was: <blockquote>"
-Εκ γυναικός τα χείρω." (''Ek gynaikós tá cheírō'')</ br>" -Kαι εκ γυναικός τα κρείττω." (''Kaí ek gynaikós tá kreíttō'')</blockquote>
His pride wounded by Kassia's terse rebuttal, Theophilos rejected her and chose [[Theodora (9th century empress)|Theodora]] as his wife.