Dear Prudence

Financial Affairs

I want to bequeath money to my mistress in my will. Is that wrong?

Get Dear Prudence delivered to your inbox each week; click here to sign up. Please send your questions for publication to prudence@slate.com. (Questions may be edited.)

Got a burning question for Prudie? She’ll be online at Washingtonpost.com to chat with readers each Monday at 1 p.m.  Submit your questions and comments here before or during the live discussion.

Dear Prudence,
I am a 60-year-old man who has been married for 30 years and has two grown children. My wife and I both earn ample incomes and are very comfortable financially. For almost a decade I’ve been having an affair. My mistress is an artist in her 40s, a wonderful woman whom I’ll call “Peggy.” We have a real emotional connection. I’m not her sugar daddy—I’ve never given her more than a few gifts or paid for meals and hotel bills. I have just been diagnosed with cancer—perhaps curable, but the statistics are terrible—and I would like to make a provision in my will for Peggy. The sum would make little difference to my family but would mean a big difference for Peggy. The danger is if my wife and kids find out, they’ll be devastated. I’ve talked to a lawyer who outlined ways to do it discreetly. I know adultery is wrong and I should never have had an affair. But morally speaking, what do you think about my plan for Peggy?

—At a Loss

Dear At,
Since you’ve been able to hide your infidelity for almost 10 years, you must use your skills at subterfuge to make sure your bequest is concealed for eternity. I agree you should follow the expert legal advice you’ve sought on how to arrange for money to be given to Peggy so that it doesn’t raise questions about that missing 401(k). It might be that you want to start giving her money now so that you can oversee it. Although you say it’s wrong to have had an affair, it doesn’t sound as if you really think so. You’ve managed to have an exciting, younger partner while not having to endure the misery of divorce. I note that you use loving words to describe Peggy, but the only thing you have to say about your wife is that she’s a good earner. You’ve got enough to deal with without my moralizing, but let me just point out that since your wife will be the one seeing you through this illness—and I hope your treatments are successful—maybe you want to try reconnecting with her emotionally, if that’s possible. Whenever your time does come, no matter how well you’ve tried to cover the money trail, there’s the possibility that your gift to Peggy may come to light. To address that contingency, I think you should write a letter to be held by your attorney and opened only if your relationship with Peggy is revealed. In it, say you were far from a perfect man, but you hope your family never doubts the depth and endurance of your love for them, and that is what they will remember when they think of you.

—Prudie

Dear Prudence: Fear of Heights

Dear Prudence,
I was having lunch today at a Japanese restaurant, and I felt very insensitive enjoying my sushi without having a way to express my sympathy for the people of Japan over the recent earthquake and tsunami. I was at a loss as to how one might state that, though, without appearing rude or overstepping boundaries. After all, I didn’t want to act as if the people in the restaurant were more Japanese than American, but most were speaking Japanese to one another, so I’m betting more than a few have ongoing connections to the country. I felt that I was acting as an insulated American by not acknowledging the situation. What is the appropriate gesture at a time like this?

—Awkward Diner

Dear Awkward,
You had no more obligation than that of being a good customer who left a decent tip. Surely, the other patrons were enjoying their meal, too, even if they were discussing what was going on in Japan. If you felt awkward sitting there, imagine the discomfort you would have caused by going from table to table expressing your condolences for the losses caused by the tsunami. If you really felt moved to say something, when your waitress presented you with the check, you could have said that you are so sorry for the suffering in Japan and that you hope any family or friends she has there are well. But I’m sure she didn’t take your silence about the tsunami as indifference.

—Prudie

Dear Prudence,
My wife and I are friends with a couple, “Sam” and “Janet,” who have two small children, a 2-year-old and a 1-year-old. Sam and Janet are connoisseurs of high-quality, natural foods. Both of them are rail thin. Sometimes Janet just forgets to eat, and apparently she also sometimes forgets to feed the kids. Last night, my wife was out with some mutual friends who told her that Sam and Janet’s kids are not getting enough to eat. They think it’s causing behavioral problems and maybe even health issues for both children. We’ve all noticed that when they visit, the 2-year-old grabs food and acts as if he’s hoarding it. And at their house recently when Sam fed the baby applesauce, she wailed every time he removed the spoon. Our mutual friends brought up their concerns with Janet, who blew them off. Since we are the couple closest to Sam and Janet, our other friends asked us to say something. I’ve concluded that the effect of any intervention would likely be a wrecked friendship. Since their behavior seems to be a character flaw, I think we should just distance ourselves from them. My wife disagrees. What should we do?

—Worried

Dear Worried,
It’s possible that two rail-thin people have begot two rail-thin children, and that what you think are behaviors driven by hunger are just the normal, highly changeable emotional states of small children. It’s also possible that Sam and Janet are so kooky about food that their children really are malnourished. If all of you think that these children are not getting enough to eat, shunning their parents is not a solution. I think the best course would be for all of you to write a letter to the children’s pediatrician—you can keep it anonymous if that would make you more comfortable. You can say you are a group of friends who know Sam and Janet are loving parents, but you are afraid they have a blind spot around food. Describe factually the situations you’ve seen that have led to your concern, and say you felt this needed to be brought to a doctor’s attention. A pediatrician has a legal obligation to report possible abuse or neglect, so any physician would take such a letter very seriously. This doesn’t mean that your friends will be turned in to the authorities, but the pediatrician will be alerted that she or he needs to find out what’s going on and intervene with Sam and Janet if necessary. If those kids are hungry, you will be saving them years of misery by acting.

—Prudie

Dear Prudence,
My siblings and I are throwing a surprise anniversary party for our parents. We’ve invited their families and friends and are looking forward to the event. This week, I looked at the RSVP list and realized we’ve invited a couple we shouldn’t have. The wife is an old friend of my mom’s, but recently they’ve had a falling out, and things are ugly. I don’t know how I missed this when I approved the list. They’ve said they’re coming, but I really think it would ruin a nice event and greatly upset both of my parents. What do we do?

—Stressed Son

Dear Stressed,
Rescinding invitations is done only under dire circumstances. One example is the Obamas withdrawing the invitation of Cat Ommanney, the now ex-wife of photographer Charles Ommanney, to a White House Christmas party for the press. The reason was guilt by association—Cat was one of the The Real Housewives of D.C., and the crashing of a White House state dinner by another housewife resulted in congressional hearings. The fact that your parents’ ex-friends accepted the invitation is poignant; maybe they think this is an opportunity to repair the breach. However, since this is a surprise party, you run the risk that after you say, “Surprise!” your mother’s expression, upon spotting her “friend,” will go from shock, to delight, to distress. If you and your siblings feel the ugliness between the women will cast a pall on the entire event, then you need to call the friend. Explain that you feel terrible about this conversation, and the fault is all yours, but when you sent the invitation you were unaware there were difficulties between her and your mother. (This white lie is justified to make the conversation easier.) Now that your siblings have filled you in, you hope she understands that you think a surprise party is not the place to work things out. Of course, depending on how ugly things have gotten, steel yourself for the possibility that the friend could still show, or even be vindictive enough to ruin the surprise.

—Prudie

More Dear Prudence Columns

A Cornucopia of Crises: Prudie takes on Thanksgiving quandaries involving uninvited guests, the ghosts of holidays past, and exiled smokers.” Posted Nov. 18, 2010.

Bob & Carol & Ted & Malice: My parents’ swinger friends are trying to blackmail our family after Mom and Dad’s tragic deaths.” Posted Sept. 30, 2010.

No Debt of Gratitude: I borrowed cash from Dad to care for my dying mom. Now he’s demanding payback.” Posted Aug. 12, 2010.

Dirty Pretty Things: My girlfriend has worn the same undergarment for weeks. Isn’t that disgusting?” Posted Aug. 27, 2009.

More Dear Prudence Chat Transcripts

The Grinch Who Stole Thanksgiving: Prudie counsels readers on Turkey Day predicaments, such as flying solo for the holiday, hosting irritating in-laws, and attending multiple dinners. Posted Nov. 22, 2010.

Baby Mama Drama: Prudie counsels a sleuth who uncovered a baby-trap scheme—and other advice-seekers.” Posted Nov. 1, 2010.

The Family That Bathes Together: Prudie counsels a mother who wonders when the time is right to stop bathing with her little boy.” Posted Oct. 12, 2010.

Help! I’m Too Hot for My Age: Prudie counsels a woman whose youthful looks bring her nothing but problems—and other advice seekers.” Posted Feb. 8, 2010.

Like Prudie on the official Dear Prudence Facebook page and like  Slate on Facebook. Follow us on Twitter.