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Published Letters: 2
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I think that ensuring the security of a guest's belongings is part of the responsibility of a host, and that the host's offer to refund the $1,000 was only fair. I also think that the LW's father is being unnecessarily hard on the boyfriend, considering the difference in their positions and incomes.
At the same time, I think that the boyfriend will have to pay up if he is truly serious about the relationship. Even to someone who already has a lot of income, $1,000 is never just "disposable". People who have amassed a lot of wealth tend to know the value of money.
I don't think the LW's parents are just going to forget about the money. They will probably hold it against the boyfriend for some time. If he is planning to take the relationship to the next level, I think he should pay up as quickly as possible to avoid friction with the parents in the future.
I've read Cary's column for ages and this doesn't sound like him at all. "THIS GUY IS NUTS" in all caps seems stronger than something that Cary would normally say. Very strange.
As for the LW, she needs to get out as soon as she reasonably can. Better to be single than to be a prisoner.