Anna Norton used to be fat. Correction: Anna Norton used to be a fat, nerdy, overeater with low self esteem. When she moves from suburban Ohio to Manhattan at age 23, her life does a total 180. With guidance from her boss, an unlikely Fairy Godmother in the form of a chic caterer and excellent cook, Anna loses all the weight and--though still not quite Kate Moss--finally drops her inferiority complex, brushes the crumbs off her skirt, and enters the world of feeling good, looking good, and...finally having sex.
When Anna meets Ben, the man of her dreams (and of every other person's dreams who isn't blind) she almost can't believe she is dating the Ken Doll. Deep down, she is still the chubby nerd who wrote in a diary called Hello Fatty. But not everything is perfect; her hot boyfriend is a huge flirt, and every leggy blond who crosses his path is a threat to Anna. She just can't escape the feeling that Ben is way out of her league and that everyone thinks she is dating up and he's dating down. It gets so bad, she decides she will do anything to make these women go away.
Enter the Makedown. The reverse makeover. As Anna was made up, so will Ben be made down. Where she went from shabby to chic, he will go from prince to frog. Anna will sabotage his hotness for the sake of her own sanity, and to bring this man into more of what she considers her own league. Enter Nair to induce premature balding, Sears catalogs to inspire bad dressing, and secret additions of cream to her cooking and SKOR bars in granola bar wrappers to induce weight gain. Hilarity ensues, but in the end, Anna must find out if Ben's makedown will save their relationship, or end it.