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What Would It Take For You To Be A Mistress?

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My close friend Shelley -- a 38-year-old divorced mom and full-time student -- was sitting alone in a Calgary cafe when conversation struck up between her and an attractive man at the next table. She judged him to be around 50, he was well-dressed, well-spoken, and had a confident, warm air about him.

Turns out that this man - who did not hide the fact that he's married with three grown children in Toronto -- owned a technology business, with offices in various Canadian cities. And coincidentally, technology happened to be the field of Shelley's studies. So when he asked if they might continue their conversation over lunch (he was "starving"), she didn't hesitate to say yes.

Over the next hour, conversation gradually veered into more personal territory. When he asked why a beautiful, smart woman such as herself was single, she said that she wasn't even looking; school and her kids were her focus. Things were tight for her financially too; it was actually stressing her out. She'd also recently exited a long term relationship, and felt she needed time to heal.

He, in turn, began opening up about his situation at home. He said he loved his wife and the life they'd spent 25 years together building. But his wife also had no interest in sex; she hadn't, in fact, for years, since reaching menopause. He said he'd found himself growing increasingly resentful towards her - his sex drive was alive and well. Instead of allowing the issue to potentially lead to a divorce, he'd chosen to take a mistress on the side.

Shelley was surprised by his confession. She had mixed feelings about it too. Six years earlier, her ex-husband had cheated and left her for another woman; she knew the excruciating pain of infidelity. At the same time, this man seemed genuinely protective and in love with his wife -- not love of the "wild, passionate" variety, but the kind that comes from growing, sharing, and supporting one another over time.

Shelley suddenly felt like she had no right to judge. She hadn't been married for 25 years, she didn't know the challenges that came with that. Strangely to her, a part of her even felt respect towards him -- for not forcing his sexual wants on his wife and honoring her body; for doing whatever he could to avoid the brutal destructiveness of divorce; for having his sexual needs met discreetly, with one other woman verses bed-hopping, and with a desire for harmlessness towards all.

Shelley had never looked at these issues from this perspective before. And she pondered: Is it really fair for him, or any married spouse, to be forced into abstinence because the other person unilaterally decides she/he no longer wants it?

Shelley proceeded to ask him more questions about his mistress and their relationship. Among other details, she learned that his lover was 15 years younger than him, they met two to six times per month, usually at her place, and he paid her a monthly allowance.

Then came the clincher: Their relationship had ended a few months ago - and he was hoping to find, and spoil, another mistress based in Calgary.

"So in essence, you're looking for a sugarbaby?" Shelley asked shocked. "Isn't that what it's called?"

"Some call it that, yes," he said quietly. "But I'm not interested in really young women. I need to have a strong mental connection, not just physical. I need mental stimulation and chemistry on all levels --" He swayed his hand back and forth between them. "Similar to what's going on here."

And that said, he locked eyes with her deeply.

Soon after, as they said their goodbyes in the parking lot, he handed her his business card. He said he'd like to see her again next week. In the meantime, would she stay in touch via email?

Shelley hasn't given him an answer. As she weighs the pros, cons and ethics of his proposition, she has turned to me to both unload and ask for guidance/coaching. I'm not pontificating or telling her what to do; rather, I'm helping her ask herself a lot of hard and honest questions, in the belief that she can make the right and best choice for herself.

With her permission -- and having changed her name -- I'm now putting it out there to you: What would you say to "I'm looking for a mistress I can spoil"? Given Shelley's present financial and personal circumstances, might an arrangement not be a win-win? As for his wife, is it a win, lose or draw?

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