Fifty First Dates After Fifty

Fifty First Dates After Fifty is a frolicking, often racy, memoir. After a seven-year relationship ends—with a man author Carolyn Lee Arnold describes as “a happy Buddhist beach boy in his late fifties”—she longs for a new partner to fill the emotional, physical, and spiritual hole in her life. It’s noteworthy that during their coupledom, Arnold lived in California, while the Buddhist boyfriend called Hawaii home. With an ocean between them, they met once a month—an arrangement the author described as perfect. This bit of backstory cues the reader that Arnold, in her fifties, isn’t likely pining for any stereotypical version of happily-ever-after.

The author’s search takes the form of a research project, a commitment to go on fifty dates with fifty different men. (A twist on the plot of the film Fifty First Dates, in which a young amnesiac must relive her first date with her future husband every time they meet.) Arnold’s memoir documents the journey from date number one through to date number fifty. Along the way, she meets and gets to know all sorts of men, in a variety of settings and circumstances. Younger men and older men. Adventurous bad boys and sensitive, spiritual types. Single, married, and polyamorous men. Several of her dates fulfill one or more of the characteristics Arnold is searching for, yet finding the complete package proves elusive.

There is sex in this memoir, a lot of sex, with a lot of men—not all fifty, I don’t believe (though I wasn’t keeping count), though the majority of the narrator’s dates do involve physical intimacy. Over the course of close to two years, she dates forty-eight men. As Arnold nears that final, fiftieth date, she hasn’t yet found the “one,” but she has connected with several who serve as stand-in lovers while she continues the search.

Ultimately, the project is a success. Just before hitting the magic number of fifty dates, Arnold meets her perfect, compatible man and chooses him for her next partner in a loving, polyamorous relationship. Jay, the chosen one, says, “We save the candlelight dinners for each other, but we snack on sex with our friends.”

Fifty First Dates After Fifty is a fast, fun read. Arnold’s prose is clever, engaging, and confident. After the first thirty or so dates, the sex began to seem a bit episodic—or am I perhaps envious of the narrator’s boundless energy and that she was able to enjoy physical intimacy with so many partners, without any of the pangs of remorse or regret that can, for many, attach to sexual encounters? Arnold is unabashedly sensual and liberated throughout, in terms of her approach to sexuality and what constitutes a fulfilling relationship. Her ideal Prince Charming may be decidedly different from that of many readers, yet Arnold knows what she wants, what will make her feel happy and fulfilled, and she goes for it with gusto.