Dear Tell All: I’m a new manager in a midsized local business. I’m in my early 30s and single, and one of the secretaries on my floor has caught my eye. She’s also single and is about my age, or maybe a bit younger. I’ve spoken to her a few times and found her charmingly shy — the type of woman who probably doesn’t realize how beautiful she is. I didn’t realize it myself until recently. She wears grandmotherly glasses and nondescript clothes, and she keeps her hair pulled back. Given her awkwardness around people and her asexual vibe, you might guess she’s never dated anyone.
That was my assumption as I worked up to asking her out. If she was as virginal as she seemed, I imagined she’d be flattered by my interest in her, especially with my position in management. (To be clear, I don’t supervise her.) But then I got some unexpected intel from a coworker.
At lunch with this guy, talk turned to the single women in our company, and he told me a mind-boggling story about the secretary. According to a former company manager who’d dated her, she’s a world-class sexual dynamo. The two of them did stuff that makes 50 Shades of Grey seem G-rated, involving bondage, threesomes, sex in public places, you name it. He supposedly broke up with her because she was into kinky acts even he couldn’t handle.
This story gave me pause. I’d expected the secretary to blush and stammer while gratefully accepting my offer of a night out. But if she’s the wildcat my coworker described, I’d be intimidated to take her on a date.
How should I proceed?
S. in Sales
Dear S.: If I were you, I wouldn’t ask her out. Not because of her supposed sexual appetites, but because you seem too immature to handle a real-life woman.
The secondhand story about her sounds bogus: a piece of woman-hating nonsense from a self-aggrandizing chauvinist. Your description of her is also outrageously sexist. The blushing, stammering virgin who’ll sigh over a manager’s attentions probably exists only in your dreams.
You’re basically asking me whether this woman is a madonna or a whore. Sorry, S., but I’m not going to answer that question — not in 2017. Try me again when you’ve learned to see women as real people.
Do you have a question about life or love in Madison?
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