Both Anthony Bridgerton and Penelope Featherington found themselves in an unexpected predicament. Having lived to the scandals of their own, with Anthony being left at the altar by the Diamond of the season, and Penelope being found out by Eloise as Lady Whistledown; how can the Capital R Rake and the notorious gossip writer navigate the upcoming London season knowing that they must appease and heed the royal command of the Queen.

After the unfortunate events at her mama's ball, Penelope had decided it was time for her to leave London. As she heard Colin uttered disparaging words about her towards his friends, Penelope had lost her respect towards the man she had silently loved all these years. As if that is not enough, her dearest friend Eloise had found out her identity as Lady Whistledown and had broken off their friendship not without saying harsh and hurtful words towards her. Now without reason to be fond of high society, Penelope Featherington decided to leave the country and settle down for good in Scotland. Until an accident happens.

At the start of the 1814 season, Viscount Anthony Bridgerton had decided that he'll finally look for and take in a wife. Having interviewed most of the ladies of the ton and found none deserving, his interest was piqued whilst at the Danbury Ball when he overhears his mother and sister speak of a lady in high regard; and in their comments found that this woman shares the same qualities he had been looking for in a prospect. What will happen if he finds out that the same lady in question was no other than his sister's best friend and their long time neighbor, Penelope Featherington?