Dumped on his 27th birthday by his college sweetheart for being indecisive, Neil makes a silly bet that takes him on a wild ride through New York’s singles scene, accompanied by four testosterone-packed imbecile buddies and one crazy scheming New York taxi driver. On these madcap adventures Neil journeys from life choice paralysis to real life manhood.

Milly is annoyed whenever her mom tells her to behave more appropriate for a girl. She's just not interested in fancy dresses or prom dances. Some day her best friend's little brother offers her a potion which can make her deepest wish come true during a solar eclipse. She goes through with it and ends up with male genitals, additionally. So she has to decide if she wants to life as boy or girl. Her father, who always wanted a son, supports her in checking out life as a boy. Hence Milly changes school and starts out as Willy.

The story chronicles the first recorded meeting in the late 16th Century between British explorers-settlers and Native Americans in what is now North Carolina, and the conflicts that ensued between the two diverse cultures before this early settlement mysteriously vanished.