A freelance writer learns what it's like to be a single, heterosexual guy in an unsteady world when he's invited to travel cross-country for six months on the "Playboy Bus" in search of the Playmate of the Millennium.

Struggling writer Leif Ueland has hit rock bottom: no job, no money, no decent apartment, no girlfriend, and he’s also a really nice guy. Acutely insecure, he’s been trying to get a grip on things with the help of a mentoring therapist. Then the opportunity of a lifetime arrives: Playboy’s Playmate of the Millennium search. Dozens of cities. Thousands of women. And one man covering it all. Suddenly, Leif, a son in a family of feminists, the anti- Hefner, finds himself at the center of a vortex of erotica, sexual harrassment, plastic surgery, stripping, and, always, beautiful women. But what does it mean to be a heterosexual, single guy? Sensitivity to women’s needs? A life full of machismo and meaningless sex? Leif Ueland is about to find out—and tell all.