When fiftysomething Jessica Gabriel finds herself heartbroken and single after failed marriage number two, her adult kids convince her to explore the tumultuous world of online dating. With a new haircut, a gym membership, and a dating profile as a forty-nine-year-old, Jessica trudges through a pool of not-so-eligible bachelors - from a pothead who tells her weed makes sex better, to a much younger man who called her the name of another lover, to a dominant male with a penchant for clothespins.

Jessica's new life comes with a new job, where she's often left to do all of the work while her boss eats donuts and gossips with his three cronies. When her advice helps save her co-worker's marriage, her hope in love is renewed.

Jessica's journey is full of tears, laughter, and an astonishing amount of sex. With the love and support of her family and friends, she discovers that being alone doesn't have to be lonely.