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“Life is short. Have an affair.”
That’s the tagline for AshleyMadison.com, a “dating” website for married people who want to cheat.
I first found out about it on an online message board for moms, where some admitted to having tried it out — only to be harshly judged by other moms in the group.
But I was intrigued. I had just passed the 11-year mark in my marriage and was approaching 40 — official middle age. My husband and I had fallen into a routine of arguing, mostly about our kids and how to properly parent them, our families, money and sex (or the lack thereof). A brief stint in couples counseling had changed nothing, and he continued to eat dinner and fall asleep in front of the TV every night.
I didn’t want to call it quits. There were many things I still loved about him, and we both loved — and spent a lot of time with — our two young children. We both worked hard. Being tired and cranky was nobody’s fault.
Yet I wondered if I’d ever have the chance to feel a spark again. Eventually my curiosity got the better of me, and I joined Ashley Madison.
The website asks members to describe themselves and their desires to help enable “the best affair possible.” I wrote that I was missing that thrill of a crush, and wanted to have fun with someone confident, handsome, bright, funny, and preferably Jewish, like me. I admitted that I was undecided about whether or not I would actually go through with an affair, and said anyone who was not willing to go slow was not for me.
My registration complete, I could now officially feel guilty.
By the next morning, my inbox was flooded with exuberant invitations. After reading through dozens of responses, I started to whittle down the list. I eliminated men over 50 (too old for me) and men under 30 (too young). Anyone with naked pictures was a definite No, and I deleted emails from men who had horrible grammar. Oh, and no one cared about my preferences: most of my invites were from men who were not Jewish.
A few weeks later, I arranged my first “date.” We met at a crowded Starbucks and I watched as he strode purposefully to the barista to order his drink. He gestured to me. “And whatever she wants. What was it again? I think it had soy.”
I hate soy.
We sat down at a large, crowded table and he told me about his personal life. “My wife is beautiful, but she’s impossible,” he said. “But, she’s a good mother. I’m not going to leave her. We have three kids and we have a good working relationship.” He’d had one experience on Ashley Madison and it was a good one — strictly no strings attached, the affair lasted a few years until his mistress relocated to London.
“So, why are you looking to have an affair?” he asked. I glanced furtively at the other customers around us. Did he really just say that out loud?
“I…umm...” I stuttered.
“You’re not ready to do this,” he said. “You need to get over your guilt. Took me years, but I did it.”
Later, I sent him a chaste e-mail thanking him for his time and the coffee. He responded: “This is a rejection of YOU. YOU are not ready to do this.”
I put off dates after that, even those I had tentatively arranged. I had to face the real reason I had come to Ashley Madison: I wanted positive attention to boost my waning self-esteem. Years of feeling underappreciated, unattractive and not quite good enough as a mother, wife and employee were wearing on me. I felt useless and starved for meaning, but deep down I also knew that it was not my husband’s fault that I felt this way, and it would be a lie to say the state of our marriage was giving me no choice but to cheat.
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I was pondering my extensive list of shortcomings when an email hit my inbox, from a member named TryingItOut. “If you’re sitting on the fence,” he wrote, “I’ll sit there with you for a while.” We traded a few e-mails and agreed to meet for lunch at a local sushi restaurant.
When he arrived, he looked more or less like his photos, but with a lopsided grin and a slightly high voice. I listened to him talk about himself for 20 minutes while I nodded numbly. But when we started to talk about work, he seemed impressed. “Wow,” he said, when I told him about my job. “You must work your a-- off.”
“I do,” I said. “I’m working like crazy.”
“Good for you. I have a lot of respect for that.” He munched thoughtfully on his salad, then looked over at my food. “Are you good with chopsticks? I’m really not. You look like you’re struggling with that salad.” He called over a waiter. “Can you get her a fork? Thanks.” I was oddly touched that he’d noticed my clumsiness.
We met again for coffee a few days later, and he told me how easy I was to talk to. He started to send me emails calling me “Sunshine” and tried to get me to take a ride with him on his private jet.
“I don’t really understand what you see in me,” I wrote back. “With all your money you can have anyone you want.”
“You are stunning,” he wrote. “You are absolutely beautiful, sharp, and you don’t need to be asked twice what time it is. I will definitely be thinking about you tonight. Stop putting yourself down.”
The attention felt good, but it was also making me nervous. When we next met for coffee, he asked if I wanted to go with him as he signed up for a new gym membership. “I’m joining because you said you work out there and you like it,” he said.
We walked the few steps to the gym, where we were ushered into a manager’s office. “What’s your full name?” the man asked Gregory.
I watched as he shifted his weight uncomfortably and tried not to look at me. “Do you want me to leave?” I said quietly.
Gregory made a stop sign with his hand. “No, no.” He asked for a piece of paper and a pen, scribbled something, and handed the paper back. “Here’s my name.”
I tapped my foot nervously as my face flushed with heat.
“And can you do something for my friend here?” he asked. “She’s already a member.”
The manager smiled knowingly, as if he understood our relationship wasn’t clean. “I’ll give her three months of a free locker,” he said.
“Thanks,” I muttered, realizing that I was not going to take this, or any favor, from Gregory, ever.
As we exited the gym, I couldn’t wait to get back to work and started briskly for the stairs. He bounded after me and grabbed my hand. “Wait.”
“What?” I asked, snatching my hand back.
“I want to know you,” he said. “I want to know why you’re on Ashley Madison. I want to know why you’re not happy with your husband. Do you want a hug? Can I hold your hand?”
“I’m not discussing any of this with you,” I said, walking away. I felt disgusted.
I realized that what I sought was something that neither Gregory, nor even my own husband, could truly provide. I wanted someone to validate me — to make me feel worthwhile — when really, it was up to me to decide my own self-worth. Understanding that these feelings of confidence and acceptance could only come from me changed my perspective. I was the only one who had the power to change my situation.
I left work early that night. After I tucked the kids into bed, I joined my husband on the couch to watch his favorite TV show. I watched as he began to doze off, I kissed his cheek to stop him.
“What? What?” he startled.
“Don’t fall asleep on the couch,” I whispered.
The author of this essay has chosen to remain anonymous.