Ask Amy: Should I confront my friend about an unpaid bill?

Dear Amy: I was planning to go on a cruise with a good friend, due to leave next month.
I paid a $900 deposit to guarantee the cruise for both of us, nine months in advance.
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It was understood that my friend and I would split the total cost of the cruise 50/50.
This includes the deposit and the remaining $2,000 that would be due, plus any other related costs.
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Last month I discovered I had cancer. I need to begin a chemotherapy regime.
No cruise for me.
Since the dates were already reserved (thanks to the deposit), I asked my friend if she wanted to take another person and go on the cruise without me.
She said no, and that she only wanted to go with me.
I canceled the cruise, losing the $900 deposit (no travel insurance).
My friend had never paid me her half of the deposit because we were going to settle up on the total costs after the cruise had ended.
She has said nothing (despite broad hints on my part) about paying her half of the $900 deposit, apparently assuming that the loss was my fault (which it was).
Should I just confront her about the $450?
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Assuming my cancer will be in remission, she has suggested reserving another cruise for the two of us in October 2024.
Because of the $450 issue, I find I’m reluctant to do anything further with her.
How should I handle this?
– Feels Betrayed
Dear Feels Betrayed: It’s hard to think of cancer as something that is your “fault,” but I understand that you’ve accepted responsibility that your cancer treatment has forced you to cancel these plans.
Yes, reimbursing you for half the cost of the deposit would have been the decent thing for your friend to do. After all, she could have gone ahead to use her half of the deposit (as well as yours) by simply accepting your offer for her to enjoy the cruise with someone else. Instead of broadly hinting, you could ask her, outright: “Are you willing to reimburse me for your half of the cruise deposit?”
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If your friend wants to go on another cruise with you, you could let her plan it and also pay the entire deposit. She will then bear the financial risk you faced (in case of cancellation).
Given how this has turned out, however, it would be wisest for you two to each pay your own way separately – from the deposit onward.
I sincerely hope that your health is fully restored, in order to face this dilemma next year.
Dear Amy: My friend “Harry” is an alcoholic.
A few years ago he ended up in the hospital facing organ failure due to his drinking. Amazingly, he survived.
After that, he attended a few AA meetings via Zoom.
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He never got a sponsor or actively worked the program.
Recently, another friend told me that Harry commented that it would probably be OK for him to drink a glass of “good” wine.
My friend told Harry that this wasn’t a good idea.
I was shocked to hear that Harry is considering drinking again.
He got sober before, but it only lasted for a couple of years.
I feel like I should say something to him, but is this any of my business?
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If I do say something, how do I approach this?
– Caring Friend
Dear Caring: You should extend and continue your friendship with “Harry” by spending time with him, if possible, and by keeping in touch with him.
You couldn’t control him when he was drinking, and you can’t control him now. His sobriety is his business. He likely understands the consequences of drinking even better than you do.
If he expresses his theory about “good wine” directly to you, you could ask him, “Based on what you’ve learned in AA, what do you think you should do? What does your sponsor say?”
Encourage his sobriety and urge him to stay the course.
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Dear Amy: “Exhausted and Worn Out” described the burden of hosting a son and daughter-in-law for the entire Thanksgiving week.
Your advice to teach the daughter-in-law how to cook a turkey was so sexist! She should teach her son!
– Shocked
Dear Shocked: Many readers responded similarly.
In my defense, “Exhausted” wrote that her daughter-in-law had never cooked a turkey. She didn’t mention her son.
I was responding to her reference.
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I also think that she and I were both applying a gender stereotype to this issue, and so I agree with you.
(You can 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.)