There's the heroine, Brandi, who has issues with her parents - her parents divorced and she overheard a few too many cruel comments before her dad finally walked out. She's so terrified of being in the same situation as her mother, needy and feminine, that she essentially repudiates her Mother and everything she has taught her to be (feminine, sweet, dependent) in order to become a self-sufficient lawyer who needs nobody.
Over the course of the novel she learns a lot of hard lessons - that the fiance she picked to be the exact opposite of her father is really a lot like him; that she has become like her father by rejecting and infantalizing her mother. She has to face them, and make new choices, finding a man who will treat her right, re-forging her relationhip with her mother. And she has to kick her father out of her life entirely.
The hero, Roberto, is not as richly drawn. He's actually very hard to understand, and although his POV is scattered through the novel the reader never gets to see deep enough into his thoughts to understand his motivations and behavior. His feelings about Brandi seesaw without any apparent logic; one day he wants no commitment and is all love-em-and-leave-em, and the very next day he's introducing her to the family and mentioning marriage. His purpose in Chicago is a little unclear; he wants revenge of some kind, and redemption, but we're left to wonder what exactly that means to him - although this turns out to be easy enough to guess, and eventually I wondered how Brandi had failed to spot the obvious.
But really, so far, so good. It's in the execution that things really go awry.
"Trouble in High Heels" does two things that make me instantly hate any romance novel:
(1) The heroine is always angry or snappish or bickering, and the hero finds this adorable. There's a point after some minor trauma where the hero says something like, "Ah, there you are, snapping at me again - you must be back to yourself! How delightful!" I don't like heroines who have nothing nice to say, and I don't like the heroes who find them delightful.
(2) The book concludes with a lengthy grovel on the part of the hero. I can't stand it when the high-point of the novel, the real proof of the hero's worthiness, is that he's willing to abase himself for the heroine no matter how persistently she rejects him. On top of which, in this case I didn't think he'd done anything wrong and I had no idea where Brandi got off being angry.
But there's so much more. Here's a typical example. There's a subplot about how Brandi turns her back on ballet because her father thinks its worthless, and she says she hasn't danced since she was thirteen; except other times, she brings it up and is very proud of being a ballerina and is apparently still practicing. The ideas are there but the development is poor and inconsistent.