On April 6, 1812, two days before her 16th birthday, Penelope Featherington falls in love with Colin Bridgerton. She is walking in Hyde Park with her mother and Colin’s mother, the Viscountess Bridgerton, when he rides up on his horse. Penelope’s bonnet flies off her head and into his face, causing Colin to fall from his horse and onto the muddy ground. Penelope is mortified, but Colin laughs.

The next year, Penelope makes her debut into society, unsuccessfully. Penelope feels awkward, as she never knows what to say to people, and her mother chooses gowns in unflattering colors: “Deep inside, she knew who she was, and that person was smart and kind and often funny, but somehow her personality always got lost somewhere between her heart and her mouth” (5). That year, 1813, is also the year that Lady Whistledown begins publishing her Society Papers. No one knows the identity of Lady Whistledown, whose paper appears three times a week, but everyone reads it. Lady Whistledown reports in one column that Penelope’s gown made her look like an overripe citrus fruit.

Penelope becomes friends with Eloise Bridgerton, who is Colin’s younger sister and Penelope’s age.