Dating By the Book

By Bethanne Patrick

(Graphic: Nancy Gonzalez/TueNight.com)

From the moment we’re allowed to date (the age of which varies greatly, depending on whether you’re a precocious urbanite or a Duggar), the road to romance is full of perils and potholes. Does he like me? Does she like me? Does this dress make me look fat? Does this mascara make me look fat?

Some of these perils have been solved — or forgotten — by the time we reach midlife. Most of us know we have physical imperfections and have made peace with them, learned to camouflage them, or paid hundreds of thousands to have them eliminated (or all three). We’re more comfortable with ourselves and able to put our romantic interests at ease, too. We know what kind of situation we’re looking for, and we make sure our signals remain clear.

HAHAHA, right! Dating is just plain hard work no matter how young or old you are. If you don’t believe it, just take a look at the following mix of novels and memoirs about women pursuing love later in life — which, in our current culture, means all of us over 35.

A Round-Heeled Woman: My Late-Life Adventures in Sex and Romance by Jane Juska

Feeling sad because you’re 43 and on the shelf? Check out Englishwoman Juska’s account of when she placed a personal ad looking for “sex with a man I like” at the age of 67. “Round-Heeled,” in case you’re not familiar with the term, means a woman who has spent a lot of time lying on her back. And Juska does. Goodness, she does!

The Wild Oats Project: One Woman’s Midlife Quest for Passion at Any Cost by Robin Rinaldi

This book isn’t out until mid March, but it had to be included given this week’s theme. At 44, Rinaldo knew she would never have children (her husband had had a vasectomy); if she wasn’t going to have babies, she’d have lovers. Lots of them, of both genders and in many combos. Searingly hot, and searingly honest.

Leap Days: Chronicle of a Midlife Move by Katherine Lanpher

Not every book on this list is about sex! Lanpher’s is mostly about dating a city. Moving from the Midwest in midlife on Leap Day (yes, really) to Manhattan, a new career, and a new love life, Lanpher accomplishes quite a few things no one thinks a fortysomething woman can — and falls in love with NYC in the process.

Revenge of the Middle-Aged Woman by Elizabeth Buchan

Rose Lloyd is 48 when her husband leaves her for her own secretary—who then replaces Rose in her job as book review editor. The perfect “coming-of-middle-age story,” it’s woven in with Rose’s memories and concerns, the plot is rich and thick, like the best and most comforting kind of nourishing, filling soup. A charmer.

Motherland: A Novel by Amy Sohn

Just because you’re married doesn’t mean you’re not dating; fans of Sohn learned that from the characters in Prospect Park West. Many of those characters return in this novel, and while the action expands to Cape Cod and the Village, most of the story centers on the righteously hip Brooklyn nabe of that earlier novel. Sharp and funny.

Bridget Jones: Mad About the Boy by Helen Fielding

“Is it wrong to lie about your age when you’re online dating?” Ah, Bridget’s back, and she’s v. v. concerned about things, as usual. But this time there’s one man who overshadows all of the others. Guess what? It’s not Mark Darcy, and it’s not someone with whom she’s romantically involved. Get out your handkerchiefs, readers.

Originally Published February 10, 2015. Updated April 3, 2021.