Mary Louise, a bookish, redheaded, freckle-faced, eighteen-year-old virgin, who suffers from Asperger's Syndrome, dispenses with Tim, her loving but far too serious and conventional high school boyfriend, then thrusts herself, groin first, into the 1960s sexual revolution, pioneering concepts such as friends with benefits and serial monogamy, while earning two college degrees in statistics. Nicknamed Tookie by her doting father, she engages in often humorous escapades with innumerable unsuitable lovers, whom she seduces with her oral virtuosity. But through it all, the one thing she really wants escapes her-a man who will truly love her, despite her faults, and give her a daughter.