Is It Okay For Me To Sleep With My School Bully’s Mother?

A young reader wonders if it is okay to pursue an intimate relationship with the mother of a bully who made his life in school unbearable. 

confused black man

Hi, I’m Joseph, 24. So there is this boy I went to school with, and basically he was/is a bully. He and his friends, who all come from well-to-do and rather influential families, made my life at the time rather miserable. They humiliated me both physically and mentally, while I couldn’t retaliate out of the fear of being expelled (or maybe something worse). I hated this boy and still despise him for the experience, although he sort of taught me to be more self-confident and to realize that life is tough.

I’m a student now and have a part-time job to pay for my studies and ease the financial burden of my family. My superior is a gorgeous woman, in her 40s. She’s intelligent, independent, beautiful and… divorced. From the very beginning, she has been showing interest in me. I won’t tell you everything, but I know she’s interested in more than platonic relationship. And I really like her, our age difference doesn’t matter. I don’t know where this might lead, but I think we’re both ready to face any consequences.

The thing is, this woman is my school bully’s mother, as I gathered recently. And I’ve just asked her on a “date” to a fancy restaurant. I’m not going to lie, the prospect of sleeping with my “enemy’s” mother is rather alluring, but I do like and respect the woman. I was attracted to her before I made the discovery. What do I do? Do I tell her the truth? Should I pursue our relationship further?

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