Chase Hamilton is a wealthy, handsome, and completely disillusioned businessman. After realizing that his last three serious girlfriends all dated him for his money, he's determined to meet a woman who has no idea how rich he really is. In the meantime, though, he'll keep dating Charlene Magill, a woman who comes from a wealthy family herself, but is about as sharp as a bowling ball. Lena Magill is the director of the local homeless shelter. Born to wealth, she turned her back on the life her father expected her to lead (i.e., marry rich man, have babies, join committees, drink self into oblivion out of boredom), and chose her own path, which includes her own job, her own apartment, and her neurotic dog, Winston. Lena still keeps one foot in the world of high society to appease her father, but it's not out of any love for the company, the expectations, or the scintillating conversation. And for now, she'll keep dating Chase, even though he's as cold as stone, and thinks that she has the brains of a mouse. It keeps her father out of her hair, and prevents him from setting her up with yet another man who has a thick wallet, but no personality. When Chase hatches the idea of volunteering at a local charity to meet women, and when he shows up at a local homeless shelter, the last person he expects to run into is Charlene. Especially a feisty, dusty, and very dedicated Charlene, who is equally shocked to find the icy and formal Chase Hamilton standing in her shelter's basement. And wearing jeans, no less. Enter two meddling grandfathers, Lena's controlling father and frequently inebriated stepmother, an attempt at a blackmailed marriage, Chase's gold-digger-dating baggage out the wazoo, and a doozy of a misunderstanding, and it's a wonder that the shelter is still standing, that Winston doesn't have a doggy stroke, or that these two crazy people finally have a chance at love.