Lena Westbrook, a perfectionist and workaholic, has carefully planned and orchestrated every detail of her life. So when her boyfriend of two years breaks up with her on the night she expects him to propose, she’s heartbroken and confused. Lena flees to her beloved aunt’s home on Seattle’s picturesque Bainbridge Island to lick her wounds, but when she awakens the next morning in this magical realism romance, she is shocked to find herself in Paris—in bed with a handsome French man who seems to think that Lena is his wife.

From the elegant neighborhoods of Paris to the charming landscape of Kinsale, Ireland, to the sparkling skyline of New York City, and many other unexpected destinations in between, each time Lena awakens, she finds herself somewhere else with someone else. In each second chance experience, she’s given a glimpse of what life might have looked like had she chosen the "road not taken." And as she becomes more clear-sighted about her past decisions, Lena begins to wonder, were any of these former romantic encounters actually... significant?