Amy is Jewish, nearing 30, single, and the successful author of "Why Love Doesn't Work," a self-help book for women who aren't in love. She's also a self-described sexorexic - she hasn't had sex with a man in four years and has never had a "mental orgasm." She gets plenty of advice - from her publicist, from her best friends (a married couple), from her parents, and from a priest to whom she goes to confession - so there's lots of conflicting emotion and analysis when she starts dating Matthew Starr, a good-looking playboy who's a popular L.A. male-chauvinist-pig radio shock jock. Each of Amy's theories and rules is put to the test - people may not change, but can love work?