Cal Weaver's seemingly perfect life falls apart after his wife confesses to infidelity and wants a divorce. Lost and helpless in the single world, Cal is taken under the wing of a confident playboy, Jacob, who decides to mentor him and teach him the art of seduction. The plot cleverly intertwines several romantic threads spanning generations, proving that the search for a "soulmate" is often chaotic, unpredictable, and—as the original title suggests—downright crazy.