Dear Prudence

Who Wants to Beg a Millionaire?

My husband’s brother won the lottery but hasn’t offered to help us out.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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Dear Prudence,
My husband and his brother, who are close in age, were orphaned as toddlers. They spent their childhood shunted among family members and spent some time in foster care. They were sometimes neglected and abused, but thankfully they have grown up to have stable families. They are nearing retirement age. My husband lost his business due to the financial crisis and now works two jobs. Retirement is looking impossible. Several years ago my brother-in-law won the lottery, netting $50 million. He has bought several multimillion-dollar vacation properties and is living the good life. He and my husband have a good relationship and speak often. What I don’t understand is how he can stand to see his little brother so stressed and working so hard while he has more money than he could spend in a dozen lifetimes. Obviously he is under no obligation, but he does not seem to realize how hard it is to see how he spends his money on travel and amusements. I think he should help his brother out. What do you think?

—Not Jealous, Just Sad 

Dear Jealous,
Sure, you’re jealous, which is perfectly understandable. As you describe, through no fault of his own, your hardworking husband was battered by fate, and now the two of you are facing working until you drop. Your brother-in-law, through no effort of his own—save the purchase of a quick pick—was smiled on by fate and now enjoys luxuriant leisure. Especially since the two brothers suffered from a start in life that would have crushed many, it’s disturbing that the lottery winner hasn’t been moved to share a small percentage of his good fortune so that his brother doesn’t spend his last years scrambling to meet his basic needs. That you note they have a warm and close relationship makes this omission even stranger. Sure, he has no obligation to help out his brother, but at this point I think it’s appropriate to ask. When it comes to difficult in-law relations, I usually advise for the immediate family member do the speaking, but in this case it might soften the potential awkwardness for everyone if the request came from you. Before you act, first discuss this with your husband. He may say he finds this idea mortifying, but I hope he doesn’t try to forbid you. Then if you do go to your brother-in-law, start by saying this is an uncomfortable meeting for you, but that you are asking for his help particularly because you are concerned about the effect working two jobs is having on your husband’s health. Say that if he would consider setting up some kind of annuity that would allow your husband to get by on only one job, you two could start rebuilding toward an eventual, frugal, retirement. And whether or not rich brother helps out, do not try to get out of your financial mess by becoming avid lottery players yourselves.


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Dear Prudence,
I’m a 32-year-old, good-looking male in a stable, monogamous relationship of a year with a woman I hope to marry one day. A few months ago she moved to another city for work, a situation that will last for about a year. Our sex life is amazing when we’re together and I do not usually feel tempted to flirt with other women. However, three weeks ago I went on a business trip to a country where prostitution is ubiquitous. I paid for sex with a professional sex worker. It was great fun, much like a good back massage or other spa service. I do not plan to look for an escort here at home. As a matter of principle, I hope I will not do this again. Still, I struggle to think of transactional sex as a big deal if it happens exceedingly rarely. I should mention I was unfaithful in past relationships when I was much younger and inexperienced. Then for several years I had only casual relationships and so feel much happier committing to my girlfriend knowing that I have seen what’s out there. Should I feel bad about what I did? Should I tell my girlfriend (and why)? Would you advise her to leave me?

—It’s Not Cheating if You Paid for It

Dear It’s Not,
Your take is that what you paid for was simply a massage focused on a particular area. Nice try! But surely you know that in human geography, not all areas are equal. And while a massage should make a client happy, that’s different from paying for a happy ending. You hesitate to run this by your future fiancée, because you know that having sex with someone outside a monogamous relationship is cheating whether or not your (temporary) new partner gives you a fake name and takes cash. I’m not an economist, so I’m still trying to parse your assertion that if you pay for something, the act of exchanging money for services renders the nature of the service meaningless. You are advancing the argument that since there was no emotional connection with the sex worker, the sex didn’t count. Yet you know there’s a reason you’re not telling your girlfriend all the details about the fabulous time you had while you were away on business. You say you hope you don’t do this again. I say: Don’t do it again. If you stick with that resolution, I promise I won’t advise her to leave you.


Dear Prudence,
About once or twice a week, depending on my mood, I stop at a local convenience store on my way back from work and purchase a lottery ticket. I wouldn’t describe it as anything excessive, and I obviously have not won the lottery (yet). I spend about $80 a month, so nearly $1,000 a year. I make a good income and have little debt. My girlfriend thinks this is ridiculous behavior, a profligate waste of money, and a sign that I am irrational. I respond that I can afford what I spend, enjoy the feeling that I could hit a life-changing jackpot, and that the revenues contribute to state services. We do not have pooled finances, but if we were to do so, I know she would immediately want to veto this expenditure. Am I so bad for doing this? What responsibility do you have to your partner regarding things you like but they deride as “wastes of money”?

—Playing the Odds

Dear Playing,
Promise me that if you do win Powerball and you have a younger brother who is broke, you will give him some money. You spend about $20 a week on this indulgence. That’s the equivalent of stopping at Starbucks every day (instead of making coffee at home) or paying for a weekly movie for you and your girlfriend (instead of watching network television). Maybe your girlfriend also spends money on little pleasures (monthly facials, a sushi habit) that aren’t necessary but make her life more enjoyable. You say you two aren’t yet mingling your finances (though she seems to be monitoring your cash outlays), but before people do reach that stage, it’s necessary to have some blunt discussions to make sure you’re both on the same page in your financial bookkeeping. This means being honest about budgets (or lack thereof), the servicing of any existing debts, and how much you put aside as mad money. But your girlfriend sounds excessively mad about how you spend your money. Given that you say your finances are in good order, you can afford this $1,000-a-year habit. Since you two have not committed your lives and fortune, you should tell her you’ve registered her opinion, but this is none of her business. And if you do win the lottery you can tell her you’d never want to burden her with your ill-got gains.


Dear Prudie,
I am a naturalized U.S. citizen who returned to my country of birth, Germany, 20 years ago to care for my mother who suffered a severe stroke. I cared for her at home and eventually did the same for my father who died of cancer. I feel that I did the right thing. When I left, my only child joined the Marine Corps. My son is my pride and joy. He is a good, honest, and kind man, now married with a little boy of his own. We are an interracial family, and my son is of mixed black and white parentage. His wife brought into their marriage a little girl, who the first time we met came flying into my arms as if we’d known each other always. My daughter-in-law lost both parents when she was still a teenager, and my step-granddaughter has never met her biological father. My family wants me to return to the U.S. and live with them. As much as I love the idea of being with my children and grandchildren—I feel so alone in Germany—I can’t discount the idea of illness down the road. I have a good pension, but what happens if I become a burden on them? I’ve traveled this path, and I know what it is like to be a caretaker day in and day out. My son says, “Mom, don’t worry. I’ll always be there for you.” What to do?

—To Move?

Dear Move,
You don’t have to make such a decision all at once. Stay with your son and his family for an extended visit, say six weeks. This will be a long enough time for the newness to wear off, so that all of you can get a picture of how living together feels. Maybe it will become clear you should make the move permanent. Maybe it will become clear that one roof is an insufficient number for all of you to be under. If the latter turns out to be the case, that still doesn’t mean you should stay in Germany. Perhaps your son could turn the basement into a small suite, or you could rent an apartment nearby so that you can be in each other’s lives but not in each other’s hair. No matter what choice you make, you will eventually come to the end of your life. But don’t assume it will happen the way your parents’ did. If you stay in Germany and end up needing a lot of care, that could place a terrible emotional weight on your son, who’d want to help in some more immediate way, but couldn’t. Since you’ve done a mighty load of caretaking, you can make clear to your loved ones that you do not want them to bear that burden for you. You can discuss and put into place plans for getting the necessary professional care. But please, take this opportunity to have a rich and rewarding time with your loving family now, and stop fearing what might be.


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