Debt creates awkward dilemma

DEAR AMY>> My partner “Charles” and I were happily together for eight years.

I decided to leave our home and move with my daughter to another city for her work. The last few years of our relationship were long distance.

When he had a sudden heart attack and died, I was filled with grief and guilt.

After his death, I had to go collect my belongings from his place. While at the house, his parents volunteered that they felt his debts had died with him. I had loaned him $5,000 for his property tax. It wasn’t a secret, and he was open about this to his parents.

They sold his home for an impressive sum last year, but never offered to pay back the money he had borrowed from me.

I’m not wealthy. I am working hard and trying to stay afloat. I don’t want to sadden his parents or to come off as greedy. If he were here, he would tell me, “Girl, speak up and go get your money!”

I just can’t seem to find the words.

— Struggling

S AR STRUGGLING >> “Charles’ ” parents might declare that his debts died with him, but in reality, you have the right to collect the money owed to you. (And if my Judge Judy fandom has taught me nothing else, please get these more informal arrangements written down, signed by both parties, and dated!)

You already have a solid rationale for wanting to have this debt repaid, but your late boyfriend has supplied the inspiration.

You should write to his parents. Share a memory and point out their son’s wonderful qualities. Because it is difficult to bring up the debt, address the challenge directly: “I realize this is very awkward. I might not get the words right, but I hope you will understand. I know you are aware of the money I loaned to Charles to pay his taxes. For me, this represents a substantial sum, and I did not hesitate to make the loan when Charles needed it. He agreed to repay the loan and I know you are aware of his intent. Charles had a high degree of fairness and he always encouraged me to advocate for myself, and so I am doing so now. I would very much appreciate you settling this debt from the proceeds of his estate.”

DEAR AMY >> In your response to “Mindful” you cited a “Mars/Venus” stereotype regarding how men and women typically communicate. I loved your response and realize that this totally applies to my husband and me.

I’m going to remember that he is just trying to “problem solve” when he leaps in to “fix” my pettier complaints.

— Grateful

DEAR GRATEFUL >> The response to this topic has so far split equally along gender lines. Women see it as insightful, men do not.

Email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.