James Ryburn, Earl of Islay and heir to the Duke of Ashbrook is disgusted when he discovers that not only has his father squandered most of the family fortune, but he's also embezzled much of the money he was holding in trust for his ward, Miss Theodora Saxby (who happens to be James' best and dearest friend). The duke's solution to the problem is that James must marry Theo, or Daisy as James thinks of her as, before some other fortune hunter proposes to her, or Theo or her mother discovers the money is missing.
Theo is tall and skinny and not what anyone would call conventionally pretty. Yet Theo loves that the two people in the world who don't seem to see her as plain or even ugly are James and her formidable mother. Having grown up with James, she's only barely started considering him in a different light than the purely fraternal, when he first compromises her, and then very publicly proposes, in front of the Prince of Wales himself. The tabloids have a field day when the gorgeous and eligible earl marries "The Ugly Duchess". Despite the very romantic proposal and the glamorous wedding, they're convinced the wedding will last six months tops. As it is, James is granted only a few days of genuinely wedded bliss before Theodora discovers the truth behind her finances and his deception, and kicks him out in disgust, before he has a chance to tell her that he does actually truly love her and explain himself.
Nearly eight years later, James shocks London society to its core by walking into the House of Lords just as they are about to declare him legally dead after his long absence. The young, gentlemanly nobleman who left is now a sunburned, tattooed and fierce-looking privateer. Theo is no longer the ugly duckling, but an elegant swan, sought after for her fashion advice. Can James convince her that he always loved her, and win her back?
In When Beauty Tamed the Beast, the heroine was almost unbelievably stunning and had men falling at her feet because of her looks. Theodora is the exact opposite, young and lanky, with no curves to speak of and harsh, nearly masculine features (I suspect she'd be able to make a killing in today's society as a runway model). Yet James never sees her as anything but lovely, and when he realises just how upsetting it would be if the sarcastic and conceited young man that Theo is infatuated with actually were to propose and take his Daisy away from him, he has no choice but to carry out his father's plan. While he does deceive Theo, he also detests his father's wastrel ways, and is determined to rebuild the family fortunes and any money the Duke embezzled from Theo's inheritance. He even makes sure that Theo is granted equal rights in running the estate (which is ironically why she can turf him without a penny once she discovers what she believes to be the truth behind his proposal).
Theo is a driven young lady, with several brilliant business ideas that turn the Ashbrook estates into something very profitable. Betrayed by the man she trusted the most, she turns away from emotional entanglements and pours herself into the rebuilding of the family fortunes. As she becomes older, she also grows into her features more, and after a season in Paris, she returns triumphantly to London and becomes a trendsetter. As the years go by with no word of James, his cousin and heir, whose become Theo's closest confidant, wants her to declare him dead so she can remarry, rather than so he can become Duke. James has stayed far away from his loved ones exactly because he thought they (especially his beloved Daisy) were better off without him, yet after a near death experience, he realises that he has to win Theo back, no matter what the cost.
I liked the realistic, and rather awkward relationship between the young Theo and James (they're 17 and 19 at the start of the book). I wish Theo hadn't become quite so cold and reserved after the heartbreak she experienced, but can absolutely understand why she needed to build a protective shell around herself - considering the depth of the betrayal she felt, combined with the appalling treatment by the gossip sheets and society after her marriage. James' inability to see her as ugly, as well as his fondness for her even before he developed romantic feelings towards her was also very endearing. Plus, I'm a sucker for a good pirate story. I liked that James didn't hide the fact that pirates (or privateer, the "acceptable" form of pirates) aren't all that nice and kill people (although in this case, only other pirates who refuse to surrender). Of all James' fairy tale retellings in romance form, this has been my favourite.