Anny Applebaum is sixty-five and writes The Viagra Diaries, a San Francisco weekly column researching sixty-plus boomers looking for love. She places ads on Internet singles sites and interviews men over sixty. Is love possible in the Viagra generation? Divorced for thirty years, Anny has given up on love and concentrates on her career. She is looking for controversy and hopes that her column will bring her fame and fortune.

On a date, Anny meets and interviews Marv Rothstein, a handsome, seventy-year-old, emotionally unavailable diamond dealer. Anny is attracted to Marv, and they become involved in a torrid affair. But soon Anny discovers that the elusive Marv is a serial dater prowling the singles sites for younger women—and that he still sees his much younger ex-wife. Anny decides to write a series of columns, modeled after Marv, about a man who can't face age, calling him Mr. X.

As Anny's Mr. X columns gain recognition, she struggles with her conflict about Marv, her career hopes, relationships, and her coming of age.