Dear Blake,

I heard my old high school boyfriend was arrested. It made the news. I hadn’t seen or heard from him in more than a decade. While I’m relieved that I dodged a bullet (I am happily married to someone else now), I feel terrible for his mom. We are still friends on social media and keep up with each other. Should I reach out to her in what must be a humiliating and concerning time, or should I keep to myself?

Signed, Victoria
From Brooklyn, New York

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Dear Victoria,

I think you should definitely reach out to his mother. But only under the condition that you think she felt you weren’t good enough for her son, which mean it’s time to have fun… at her expense. Here are some suggestions. Tell her that if her son is in prison long enough, she might want to be prepared to refer to him as her daughter after a few years. Or, tell her that you are moved to tears and you feel sorry for… his victims. Or this idea. Ask his mother, when he calls her, does he use a “cell” phone. But if you want the mother to feel better, try this last idea. Tell her that the man you married isn’t nearly as interesting as her son. Explain that your husband basically just goes to work and come home, predictably buys you a new car every other year, and maintains a nice home in an upscale community. Emphasize that he his not nearly as exciting as your son is, who’s probably wanted in several states by local and federal law enforcement as he skillfully evades bullets and tracking dogs. Conclude by saying, if you married him, you’d see her regularly… when she visited you in a women’s prison. I hope this helps.