In his poetic sequence, Astrophil and Stella (1591), Philip Sidney dramatizes his speaker’s romantic ambitions of climbing the Ladder of Love. While many academics interpret the sequence as a semi-biographical work, they disagree in evaluating how deep the sequence mirrors Sidney’s life. Traditionally, Astrophil is interpreted as a surrogate for Sidney and, more critically, Stella is read as a fictionalized version of Lady Rich. However, given the inconsistency of literary evidence, a new reading of the sequence emerged and argued that Stella is Sidney’s wife, Frances Walsingham. Although this paper agrees on the surrogacy of the speaker in the sequence, a closer analysis of the poetic language used in Sidney’s sonnets would contradict these Stella’s interpretations. Furthermore, as this paper cites historical documents that confirm the non-romantic relationship between Philip Sidney and Lady Rich, a closer examination of the sequence and the historical context of the Elizabethan Era would conclude that Stella’s real identity is far more complex and multidimensional than to be a mere fictionalized version of Lady Rich or Frances Walsingham. In fact, an investigation of Sidney’s personal life and a close reading of Astrophil and Stella would conclude that Sidney’s Stella is a masked version of Queen Elizabeth.