Blackadder is in serious debt. Baldrick suggest that he becomes a highwayman to make money to pay of his bills; however, Blackadder, having no desire to get hung for wearing a stupid hat, simply decides to ask the Prince Regent for a raise. Unfortunately, the Prince is also skint, having lost vast amounts of money playing a game called "cards", where participants are dealt five cards and the goal is to give away your money to your opponents as quickly as possible (George is apparently "a natural"). He is therefore forced to search for a rich wife and hence a sizable dowry. . Unfortunately, of the 262 princesses in Europe, only two are possible matches: Grand Duchess Sophia of Turin, who is unlikely to marry the Prince on account of the fact she's met him, and Caroline of Brunswick, a woman with the worst personality in Germany!. Blackadder begins to look through the newspapers through the society pages for a potential bride, but notices a portion removed by Baldrick; an article about his favourite highwayman, The Shadow
Amy Hardwood (played by Miranda Richardson), daughter of a powerful industrialist, seems the only option despite the fact that she says things like, "What about George's lovey-wovey poems that won my hearty-wahty?". The Prince seems unlikely to succeed on his own, as his idea of a love letter includes the line "You'll be staring at my bedroom ceiling from now til Christmas, you lucky tart!", so Blackadder writes a script which the Prince Regent must follow ("Do you mind if I just change one thing, Your Highness? The words ").
The flirtation and engagement seems to be going well until Blackadder discovers that Amy's father is broke, upon which he breaks the engagement, though too late to prevent the Prince spending several thousand pounds on wedding gifts. Blackadder saddles up Baldrick and turns to the life of a highwayman. He soon discovers that Amy Hardwood is in fact herself the notorious highwayman, The Shadow. She pretends to be in love with Blackadder to steal the Prince's money and the wedding gifts, but Blackadder turns her in for a £10,000 reward. He stows the reward in the biscuit tin, but unfortunately, the prince finds it. The episode ends as an initially disheartened Blackadder overhears the Prince mention he now has so much money I don't know what to do with it!. Sensing a chance to get his money back, Edmund convinces the Prince Regent to play a game of "cards" with him.