Facing forty, can she find a man who doesn't care if she wears a thong or not? Tess Grayson has a comfortable life. When new and sexy are the must-haves for everything from phones to shoes, Tess knows she can't compete with the newer models. Content with her working-mother life, she'd rather stay home in her sweatpants on Friday nights anyway. But when a girlfriend pushes her to expand her horizons, Tess finds herself stuck with a crazy wager. Either she goes on five dates in six months, or she has to display her tone-deaf singing at the company talent show. Determined to avoid humiliation, Tess ditches the granny panties and ups her sex appeal. Through a succession of epically bad dates, her biggest supporter is co-worker Jack Maristone. He even offers to help her win the bet. Could the solution to all her problems be right next to her?