My Cheating Heart: lessons from my year on Ashley Madison

My Cheating Heart: lessons from my year on Ashley Madison

I was bored with my husband, resented my kids and yearned to feel sexy again. I was ready to have an affair

My Cheating Heart
(Illustration by Jack Dylan)

Everything you’re about to read is true. I’m withholding my name to protect my marriage, but the people, the places and the dates are just as I describe. It all began in the spring of 2011, after several bellinis at a Milestones with my best friend. She giddily whispered in my ear that she was having an affair with someone she had met on, the hook-up website targeted at married people. She pulled out her iPhone and surreptitiously showed me a picture of her paramour. He was attractive, with a chiseled face and a broad smile. He’d ended their first date by kissing her passionately—something she hadn’t experienced in years. I felt a pang of envy.

She and I had met years earlier while working for the same PR firm and had bonded over a shared crush on an extremely handsome younger colleague. We spent many lunch hours discussing our interactions with him and laughing over what we’d do if we ever found ourselves alone with him in the backseat of his silver SUV, parked in a dark corner of the company’s underground garage. Sometime after that, we started to share pulpy erotic novels with titles like Wicked Ties, Fantasy Lover and Strange Attractions.

I had recently turned 46 and dreaded hitting the half-century mark. I visited the gym more often, lost some weight and even underwent some laser cosmetic procedures, all in attempts to delay the inevitable.

My husband and I had married in our early 20s, fresh out of university. We live in the suburbs and have two children, ages 10 and 12. Our marriage is relatively healthy—we love each other and we still have sex. But over the years, the frequency had decreased from three times a week to once a week, and it was routine and predictable. I also resented how much of my life was taken up by the kids’ soccer practices, hair appointments and parent-teacher interviews.

A few months after my friend’s confession, I was working at home one weekend while my husband and kids were away at our cottage. I’d recently started a public relations job on Bay Street, and I had some urgent project deadlines to meet. Once I’d finished, I found myself sitting on my bed, a glass of red wine on my night table, my laptop resting on my thighs and my eyes fixed on the landing page of Ashley Madison, or AM as it’s known to regular users.

I was ready to have an affair.

The site listed dozens of available married men in my general vicinity: NiceGuyOakville, etobicokedude, Fun_in_Mississauga, Burlington1on1. But before I could view their profiles, I had to create one of my own. “I seek a connection with a smart, funny, mature, manly, professional man,” I wrote. “You are in your 40s, dark-haired, blue-eyed, tall, fit and attractive.” I posted photos in a “private showcase” that someone could view only if I sent them a “key.” In one photo I was wearing a little black dress at a gala dinner; in another I posed like a ski bunny somewhere in Quebec. One of the pictures captured my blond, shoulder-length hair falling over one eye, my lips full and glossy, a tight, low-cut shirt emphasizing my cleavage. I was careful to crop out name tags and anything that could reveal the location in each photo—anything that could identify me.

My husband had been nothing but supportive of my new job. He never complained when I got home late, which happened often. I should have felt guilty embarking on this betrayal. Instead, I felt turned on.

My Cheating Heart
(Illustration by Jack Dylan)

Over the next week, messages flooded my AM inbox. Most of them were off-putting, showing close-up photos of men’s erections or, worse, men with what I suspected were their kids and spouses. The ages of the men contacting me ranged from 27 up to the mid-60s. But quite a few of them were intriguing: I was approached by a surgeon at the Toronto General Hospital, a finance director with a branch of the Ontario government and a detective with the Toronto Police Service.

I was startled when I opened one AM email and discovered it was from someone I knew. “I’m the CEO of a big company,” his message to me read. “I can only meet during the day because I don’t want to risk hurting anyone at home. I will pay for everything.

I will make you feel good and am sexually open to anything that doesn’t involve pain. I hope to hear from you.” I briefly contemplated replying, as he was an attractive man. But the fact that we knew each other ultimately stopped me.

I began to spend at least an hour every day on the AM site.

I would stay up with my iPad after my husband and kids went to bed, reading and replying to messages late into the night, careful to clear my browsing history after every session.

My first date was with a realtor on a Wednesday afternoon.

I told my boss I had a dentist appointment and ducked out to the Library Bar at the Royal York hotel, wondering if we’d find each other attractive or if he’d even show. The man who arrived was at least a decade older than his profile photo. Over a drink, he told me he’d fallen in love with me. His intensity frightened me—he seemed desperate and a little unhinged. I quickly finished my drink, gently told him I didn’t feel the same way and then left, scurrying back to my office through the PATH system.

My next date was lunch with an architect at Alice Fazooli’s. He was more interested in checking his BlackBerry than in me, and we didn’t bother meeting again. Another day I met an online journalist at a downtown Starbucks. He was seven years younger than I, handsome and sweet, and he drove a motorcycle. We kissed at the end of the date and agreed to meet again, but never did—he claimed his wife was ill and he had no free evenings.

Half a dozen disheartening first dates later, I heard from a doctor with a practice in East York. The photos attached to his message showed a man who looked much younger than his stated age of 54. He was tall, with dark hair, a square jaw and broad shoulders. He smiled easily in the pictures, some of which had been taken on a boat, others in various parts of Europe. I was smitten.

My Cheating Heart
(Illustration by Jack Dylan)

We agreed to meet for dinner at Sassafraz in Yorkville. It was mid-summer and hot, and I agonized over what to wear, settling on a fitted skirt and jacket, with the top buttons of my blouse undone. I made an extra effort to primp, refreshing my hair colour, polishing my nails and fake-tanning my legs. As I made my way down Cumberland Street, I felt giddy but apprehensive. I spotted him right away, sitting at the back of the restaurant on one of its white banquettes. He stood to kiss me on the cheek.

For the next three hours we talked nonstop over glasses of white wine and plates of oysters, then walked around Yorkville, en route to the University of Toronto campus in search of a more private place to end the evening. Near the law faculty, we found a deserted walkway, and he backed me against a brick wall. He leaned into me with an arm on each side of my head and pounced on my lips. I responded with equal enthusiasm, and unbuttoned his dress shirt while his hands lifted my skirt and tugged on my panties. But we heard two joggers approaching on the path and quickly pulled apart. He walked me back to my car, and we made plans to reconnect after his upcoming two-week Caribbean vacation with his wife.

We stayed in touch all through his vacation, exchanging information about our lives and describing in great detail the many ways in which we wanted each other. We scheduled our second date for a few days after he returned, a muggy August afternoon. We met for lunch in Mississauga followed by some time at a nearby secluded park, where we lay down on a blanket I had brought along. After some kissing and heavy petting, I unzipped his jeans and discovered his penis was completely flaccid. He said something about feeling shy and quickly zipped himself back up. We left the park, and, after an awkward goodbye, I drove home, feeling confused and uneasy. The next day, he emailed me saying he was embarrassed and blamed our surroundings. Next time, he said, we needed a bed.
About a week and a half later, he booked us a room at the Best Western Primrose Hotel on Carlton. Since we were meeting around dinnertime, my task was to pick up some snacks and a bottle of wine. As I made my way over, I received a text: “I’m here. Hurry!”

I had imagined I would experience my first fling in a fancier hotel—the Four Seasons or the Ritz—not at a Best Western, but I was excited nonetheless. As I rode up the elevator, I thought about my husband, who at that moment was probably cooking something for our kids in our kitchen. As far as they knew, I had run into a former colleague in the city and we’d agreed to meet for drinks and possibly dinner. I had about four hours before I had to make my way to my car and start the drive back home.

Pushing all those thoughts out of my mind, I knocked on the door. The doctor greeted me by putting both hands around my waist and pulling me into a kiss. I wish I could say that auspicious beginning ended in amazing and satisfying sex for both of us. Once again, he couldn’t sustain an erection. After a couple of hours of trying, we found ourselves lying on the king-size bed, my head resting on his chest, his fingers caressing one of my arms. We liked each other but perhaps lacked sexual chemistry, he suggested. Adopting a doctor’s clinical tone, he explained how we’re all at the mercy of our pheromones. I asked if there was anything else getting in the way. He admitted he felt guilty—his wife trusted him completely. “Or maybe it’s an age thing,” he added. I considered asking him why he hadn’t brought some pharmaceuticals to help things along, but decided he felt bad enough as it was.

We got dressed, in the now familiar awkward silence that had become our end-of-date routine. As I replayed the evening on my drive home, I started to feel guilty, too. What was I doing, getting naked in a hotel room with a man I had met online and hardly knew? What would my husband think if he ever found out about the other men I had met in bars and darkened restaurants? Would he ask for a divorce? I knew I could lose everything: my marriage, my family, our home, our cottage.

When I arrived home, my husband was luckily out walking our dog, and I was able to take a long shower and clear my head before he returned.

Two days later, the doctor contacted me again. “If we could have our minds calm, and focused on each other only, without other distractions, guilt or misgivings, we might just have amazing sex,” he wrote. “I don’t want this to end.” I didn’t want it to end, either. Even after our awkward encounters, I was still attracted to him and had begun to feel emotionally attached.

I agreed to meet him once again, this time at the Marriott Bloor Yorkville, on a Saturday afternoon in early September. But that encounter ended the same as the last. Saying goodbye once again, we both knew it was finally over.

We had one last email exchange in which he apologized again for his inability to perform and urged me to try again with someone new. “It took me the better part of a year to find you,” I wrote back, “and I won’t put myself through that again. Too much disappointment and heartbreak that, honestly, I don’t need. I’ve decided to be content with what I have.”

A week later I shut down my AM account. But first I took one last look at the page of currently available men and spotted the doctor. It only confirmed my decision.

Late last fall, I met my best friend at a Second Cup. We had become each other’s AM affair confidantes, and I had gone to her after every failed date and every unsatisfying meeting with the doctor. Her own affair had ended after three months of countless cancelled dates and broken promises.

We postulated that half of the men on AM are players and the other half are just damaged in some way. As we sipped our coffees, she theorized that the doctor likely had performance problems before meeting me and was trying to “cure” himself.

We laughed at the absurdity of it all: after more than 23 years with the same man, I had finally been ready to have a new lover and had ended up right where I’d started. Yes, most of my days were still mundane and I was still getting older. But the experience had given me a chance to evaluate what I did have. Despite the shortcomings of my marriage, it was much better than the alternative—being with a man who couldn’t get it up.

Always one step ahead of me, my friend had been looking into sex workshops for individuals and couples at a Toronto sex store, with titles like Joystick Secrets and The Art of Feminine Dominance. “I’m thinking of signing up for Stripping for Klutzes,” she said, as we stood up to leave the coffee shop. “Wanna come?”