Amy Dickinson is a general advice columnist.
DEAR AMY: My sisters and I discussed taking an overseas trip. There are five of us. I found a great vacation package and ran it by all of them. We were all in agreement that this was perfect, so I asked if they would all be ready to purchase. I explicitly stated that, although we all agreed to put the trip on my credit card, I would need immediate payment from all of them, and that if anyone was not ready to pay, that we could hold off. All of my siblings said they had the money in hand. It's now over two months later and one of my sisters, "Cathleen," has not paid me. Before my credit card payment came due the first month, I asked if I could expect her check in the mail soon. She said she didn't have it because she had since purchased another trip with her boyfriend. The second month, she again stated she didn't have the money. My other sister talked to Cathleen, only to find out that she has made another large purchase and that she doesn't feel she needs to rush to pay me since I "have money." (My husband and I are upper-middle class, but are by no means rich.) How do I ask her for the payment? I'm afraid of upsetting her since she and I have had a rocky relationship at times, and I don't want this trip tainted by money issues. The trip is nonrefundable and I'm in the hole.
DEAR STUCK: You should start by taking this to "Cathleen" directly, and depending on her answer you could take it to the group.
Email her: "Your payment for the trip is so late that I'm now in the hole for your portion. Do you still want to go on this trip? Let me know one way or another so we can all decide what to do." If your sister isn't going to pay for her portion of the trip, one option is for the rest of the group to absorb and share the cost, so that you aren't left holding the bag alone. If the four remaining sisters share the burden equally, it will put all of you on the same page regarding her debt.
DEAR AMY: I have a friend of over 40 years, who has been sharing all kinds of private information about me with others. The most troublesome is her compulsion to brag about every party of mine she goes to, to people who were not invited. It has already ruined one long friendship with a woman she knew was touchy about such things. I have asked her to stop, and she promised she would, but the behavior has continued. As my punishment for confronting her about this, she dropped me from her guest list, but I forgave her and continued to invite her. She also repeated some deeply personal information about me to others -- information she had promised not to tell even her husband. I am shocked at such indiscretion. After so many decades, I hate to walk away from her, in part because it will be difficult to avoid running into her, but it seems impossible to get through to her, and I don't want any other friendships ruined. Any ideas?
DEAR M: You made a reasonable request of your friend and she punished you for it. It doesn't seem there is much of a friendship left.
If you run into her, you should be cordial, if tight lipped.
DEAR AMY: "Frustrated in New York" wrote because her mother-in-law did not recognize her birthday or her daughter's birthday, but gave her husband a gift and a visit shortly thereafter on his birthday. You suggested her mother-in-law might have been feeling unappreciated. "Frustrated" has been married 26 years so her mother-in-law is probably at least in her 70s. I suspect she had a senior moment. "Frustrated" said this has caused major trouble in her marriage. If this is the biggest thing she has to worry about, she is very lucky. Let it go.
A Denver Senior Mother-in-Law
DEAR DENVER: Good advice.