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Dear Annie: I’m writing in response to “Grieving and Not Prepared for a Confrontation” whose husband died before he could recoup a sum of money he lent to his brother; now, she needs that money and is looking to collect. Your wishy-washy advice to this widow on how to approach her brother-in-law Simon was like advising her to take a water pistol to a gunfight!

This ungrateful brother already “exploded” and made his position clear. “Grieving and Not Prepared” needs to teach this ingrate a lesson, hire a lawyer and subpoena the sister to verify there was indeed a loan that he admitted he would not pay back! This irresponsible jerk should face the music.

— Enough Is Enough

Dear Enough: You’re right that Simon needs to be held accountable for his actions — or lack thereof. Seeking the advice of a lawyer is a surefire way to determine what options “Grieving and Not Prepared” has in her situation.

When it comes to people like Simon who are set in their ways and don’t play by the rules, the only hope for getting them to listen is taking action.

• • •

Dear Annie: I am a happily married middle-aged woman. In high school, I had a relationship that continued off and on for a few years until he cheated on me and we finally went our separate ways.

About 15 years ago, he bumped into my sister, and we got back in touch via email. It was cordial, and we mainly shared information about our spouses and children. One day, he called my office, and when I asked him why he was calling, he said he wanted to know if there was “anything left.” I told him that there wasn’t and that I had married my soul mate. He accepted that, and we went back to annual Christmas cards and emails of family updates.

About eight years ago, I started to feel like I didn’t want to continue communicating (he’d sent an email that made me uncomfortable), so I stopped responding to his emails (he sends one every year on my birthday).

A few weeks ago, I got a card at my office saying he remembered that in college, I had a new down coat that was stolen from his apartment and that he was planning on sending me a new one. I recycled the card and thought nothing more about it. Last week, an expensive down coat arrived at my office with a note saying it was a replacement for the one I lost 47 years ago. I returned the coat.

I’m baffled. I’m not sure if I should email him and ask him to stop communicating with me or continue to not respond. I thought that my eight years of silence would show him that I wasn’t interested in communicating with him, but now I wonder if it just created a space for him to fill the silence with what he wants to believe. What should I do? Thanks for any advice.

— Stumped

Dear Stumped: While most people would indeed interpret silence as disinterest, your ex clearly needs a more straightforward message. Send him one last email with any and everything you have left to say. Explain how uncomfortable you feel, and though that likely wasn’t his intention, you don’t wish to communicate with him anymore in any capacity. Block him on all communication platforms.

If he continues reaching out or contacting you through your work, reach out to your local police department for guidance on how to proceed. Your safety and security are chief concerns in this situation.

Send to dearannie@creators.com.