Penelope enters determined to move on from her long-standing crush on Colin. However, she hasn't given up on love altogether. Instead, Penelope is ready to find a husband-one who will allow her the freedom to maintain her double life as Lady Whistledown, far from the prying eyes of her mother and sisters. Yet, her lack of confidence leads to spectacular failures in the marriage market. Meanwhile, Colin returns from his summer travels with a new look and a newfound swagger. He is disheartened to discover that Penelope, who always valued him for who he was, is now giving him the cold shoulder.
Determined to win back her friendship, Colin offers to mentor Penelope in building her confidence to help her secure a husband this season. However, as his lessons begin to work too well, Colin is forced to confront his own feelings and question whether they are purely platonic. Adding to Penelope's challenges is her rift with Eloise, who has found a new, unexpected friend. As Penelope's presence in society grows, keeping her Lady Whistledown alter ego a secret becomes increasingly difficult.
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