The online dating adventures of an older woman.

This post originally appeared on RoleReboot and has been republished here with full permission.

One guy told her she needed to lose 40 pounds. Another said he just wanted to ‘give an older woman a try.’ And another said she had too much baggage.

He told her he loved the way they could talk for hours about everything under the sun: Obama’s second-term trials, whether gluten-free diets were a food-company ruse, Robin Williams’ tragic end. Her four kids and his three. Her one long marriage; his two fairly short ones. What had gone right, and what had gone terribly wrong in their previous lives. Nothing was off-limits.

He took her hand in the movie theater, shared his popcorn, and let her bury her face against his shoulder during the violent parts. He cooked her exquisite dinners in his large, open kitchen and poured the perfect Chardonnay or Pinot Noir to go with them. He held her close in bed after they made love, in that space where people feel safest and most vulnerable at the same time. He stroked her hair and whispered that she was beautiful.

Then one morning when they were getting dressed, he sat down beside her, looked into her eyes, and said this: “You and I have something really special together. If you lost 40 pounds, I think we might have a shot at going the distance.” His words landed on her ears like a needle skittering across a vinyl record on an old turntable. There was shock, then dissonance, then pain.

We’ll call him Boorish Bob. But there were others—Ill-Mannered Al, Fetish Frank, Critical Ken, Asshole Art—all gleaned from promising profiles on an Internet dating site Sue started visiting after her divorce from Cheating Chet became final.


Now, Sue is no babe in the woods. She’s just on the shy side of 60, a professional woman who’s managed to hold her own in the male-dominated world of business. She’s funny, confident, well-read, and can dance a mean salsa.

And yeah, Sue’s a beauty—a catch who loves life but doesn’t like living alone. So one night when she was surfing the Internet, she took the plunge on OKCupid and filled out information designed to fill in the blanks of who she is: a dynamic, talented, adventurous, past-middle-age lady with a Buddha tattoo just above her left breast. She’s brassy and little bit bawdy. She makes noise when she eats, listens to Vivaldi and Clapton, and cherishes walks around her suburban Portland neighborhood with her two daughters who live close by. She teaches her grandkids proper manners and silly songs both.

She uploaded a photo of herself that showed off her steel-blue eyes and her winning smile. It also hinted at her fun-loving spirit and revealed a few well-earned wrinkles. Air-brushing wasn’t on her agenda. She clicked “done,” and waited. It wasn’t long before she was instant-messaging with a half-dozen guys—some retired, others still company men, a few latent poets and dreamers. The conversations were telling.

She knew right away some of the would-be suitors weren’t right: one copped to five marriages; another said he had an issue with cocaine; still another wrote that his ideal date would involve bourbon and sadomasochism. No thanks, Sue said. She was more interested in a gradual courtship with strolls along the beach and rides in the car. She wanted to slurp spaghetti and indulge in long, lazy afternoons entwined in a man’s arms.


She eventually said yes to Doug, Jim, Bill, Steve, and John. They met at coffee shops, in diners, at the racetrack, in a shopping mall. Two were artful lovers. The rest weren’t interested “in that sort of thing anymore.” Huh, Sue thought, pecking those guys on the cheek before returning to her home office and checking the “Don’t contact me again” box under their names.

"They met at coffee shops, in diners, at the racetrack, in a shopping mall."


She accepted dates with Jeremy, Cody, Marcus, and Ryan during her self-proclaimed cougar phase. One was voracious but clumsy in the bedroom. Two left her breathless and wanting more. The fourth was too shy to ask, even after she took off her clothes. She was learning so much.

Sue’s date with Doug lasted less than a half-hour because he came right out and told her he was interested in younger women but had thought he’d “give her a try,” even though her age was clearly listed on her profile. She left the pizza joint and caught a cab home. Things seemed to be going along swimmingly with Steve until he discovered Sue was a mother and grandmother—“too much baggage,” he said, even though he himself was a dad three times over and step-dad to two thirty-somethings—leaving Sue to wonder if all of them knew this lout regarded them as yesterday’s stinking leftovers.

Jim said she was too loud, Bill pronounced her too quiet. John listened impatiently while Sue related her past travels to Mexico and Hawaii, then spiked the ball by going on about his sojourns to Nepal and Greece and Indonesia. Bali was “to die for,” he insisted, and in that moment she wished he would.


Still, she was willing to give John a second chance, so they met again, this time for a moonlit cruise on the Willamette River. During dessert (Baked Alaska), he bragged about all the shades-of-gray ways his accountant had saved him money, making it clear he had boatloads of it. He couldn’t part with it when it came to Sue, however. When the check came, John was conveniently indisposed in the men’s room.

After 12 months of giddy anticipation, escalating hopes, a few torturous evenings and a handful of dashed dreams, Sue’s Excellent Online Dating Adventures have left her ambivalent about whether to push ahead or pull the plug. She has offered herself up to the relationship gods and come up empty. It isn’t as if Sue hasn’t done her personal due diligence in the form of reflection. She’s willing to go white collar or blue collar. She isn’t overly concerned about whether a man has studied Auden or Yeats or if he can recite something from Mary Oliver. If he has a good sense of humor and a passion for the future, a shortage of muscle mass or an abundance of nose hair won’t necessarily send her running. She just wants real—Velveteen Rabbit real.

When, she laments in the silence, will someone love her for who she is rather than who they wish her to be? Why can’t Prince Charming grow up, put on big-boy pants and finally, mercifully, turn out to be Mr. Right?

Bathed in the pale-blue light of her monitor, Sue sighs and clicks out of OKCupid. She shuts down her computer, picks up the latest issue of People and dons her chenille bathrobe. She lights a candle. For this night, anyway, she unplugs.


Nancy Townsley is managing editor of two community newspapers, the Hillsboro Tribune and the Forest Grove News-Times. Her work has most recently been published in NAILED Magazine, Brave on the Page: Oregon Writers on Craft and the Creative Life (Forest Avenue Press), the Riveter Magazine,, and Bleed, a literary blog from Jaded Ibis Press. She lives in St. Helens, Oregon.