Trentonian Stacy Holt's life has been guided by two general items. One is her father abandoning the family when she was young, leading to her and her mother turning to the music of Carly Simon to cope, and she having had a history of unsatisfying romantic relationships in not having a suitable male role model. The other is her idolization of Diane Sawyer, who she has long wanted to work alongside as a serious journalist. Her personal life seems to have finally overcome the issue of her father with the entrance of Derek into her life, he, a scout for the New Jersey Devils, her boyfriend who she knew was her soul mate when they met, they now living together. Things are not going as well on the professional front, she having just left a dead end job to work among the large stable of associate producers on the syndicated Trenton-based daytime talk show "Kippie Kann Do!!", whose show topics are outrageous, the more outrageous the better. Stacy's tenure with the show is even more tenuous as Kippie herself has been the fodder for the tabloids, Stacy further learning that someone on staff has been feeding the tabloids those stories in trying to push Kippie out with cause as there is five years left in her contract. When Stacy learns that Derek once dated supermodel Lulu Fritz, who has appeared on the talk show circuit, including on Kippie's show, in discussing her bulimia, Stacy begins to wonder what else about his dating past Derek has failed to mention. This item comes to a head when Stacy has access to Derek's palm pilot to discover that he has been in recent contact with at least two former girlfriends, both equally as successful as Lulu, and neither which Derek had ever mentioned let alone about this recent contact. In general discussion with her work colleagues in a show idea of snooping in a significant other's little black book to discover what secret life that person may be leading, Stacy, with her two confidantes among those colleagues, Barb Campbell-Dunn and Ira Nachlis, by her side, goes about delving further into Derek's proverbial little back book - his palm pilot - by contacting those former girlfriends under an assumed name to find out more information about their relationship with Derek under the guise of possible appearances on Kippie's show about their work lives. Beyond the issue of if the secrets Derek may be keeping are a bigger picture of the doomed fate of their relationship, Stacy may discover more about herself and her life in general, partly in relation to the issue of the old quote, "luck is what happens when preparation meets opportunity".