Photo

In the years that I’ve spent writing about parenting, money and values, I’ve wrestled with scores of challenging questions about this often taboo topic. But I can’t think of many that stumped me more than the one that arrived via e-mail a few weeks ago.

The mother is herself a parenting expert — a mental health practitioner and a professor — who asked to remain anonymous to avoid antagonizing her former husband.

When their preteen son is with his dad, he gets a great deal of what he wants. If he starts a new sport, he gets an official jersey from the local pro team with his name on the back. He has the iPhone and the iPad and the game consoles and all the rest.

Then, he returns to his mother and her new husband (sometimes with a $100 bill or some $20s stuffed in his pocket), with rules to follow and chores to perform. If he doesn’t do his chores, he doesn’t get his allowance. But it’s a bit of a hollow threat, given that he doesn’t need his mom’s money. So he’s not exactly racing to do his assigned tasks.

She has tried to get his father to cut it out, but it hasn’t worked so far. “I’m somewhat certain his father buys him things and trips to make up for lost time,” she said in her note to me. “But our concern is his doing so will ultimately cripple our child’s ability to grow into a financially responsible teenager and adult.”

Despite her training, she said she was totally stumped as to what to do next. I reminded her that deliberate overindulgence is something just short of parental malpractice, but we decided that levying that charge wasn’t going to go over too well with the ex’s lawyer.

So I turned to Cindy Thompson, a financial planner who specializes in helping clients who are divorced. She is divorced herself and notes that her teenage children ended up with a sports car (that nobody consulted her on) that was worth nearly as much as the purchase price of the first house in Texas that she and her former husband had bought together.

Even if it’s less expensive trinkets, Ms. Thompson added, the gifts can serve as weapons when one parent is left with less money after the divorce or simply chooses to do things differently. “This sort of thing is incredibly common, and it can be incredibly painful,” she said.

She had four suggestions.

1) INTACT TEETH “You can’t ever really change another person, when you’re married and when you’re not married,” Ms. Thompson said. “It’s a lesson you only have to learn until the day you die. You learn it and relearn it, so tell her not to break her teeth against the pavement while trying.”

Indeed, the mother in question had lost some degree of hope in this regard after her former husband called her a hippie in the wake of one such attempt to recalibrate his parenting.

2) NO CRITICISM Bad-mouthing the other spouse is usually a loser’s game. You may feel slightly better, sometimes, but the child suffers in the long term.

Besides, having a child watch you do something differently is not necessarily bad, even if it’s confusing at first. “Be upfront, and tell him that in this house, we do chores,” Ms. Thompson said of the young man in question. “You don’t control whether he’ll model your behavior later, but eventually he’ll draw his own conclusions.”

3) ABANDONED BOXERS Ms. Thompson is among a small but vocal minority who believe that paying kids to do basic household chores is misguided. If compensation does not motivate the boy in question when he’s at his mother’s house, she might try adjusting her approach and clarifying that chores are something everyone just does, including parents and stepparents.

“Just say that we both love you tremendously, and we’re not going to raise a child who thinks someone else picks up his boxers at the toilet or rinses his dish,” she said. “Tell him that the two of you are doing him, his future romantic partner and his future roommate a favor.”

4) MONEY ISN’T BAD One temptation here would be to default to the assumption that it’s money and gifts themselves that are in danger of perverting the boy’s values. But that isn’t quite right.

“Encourage him to be thankful, to enjoy it and don’t disparage it,” Ms. Thompson said. “You’re never going to convince a child that he really has to try Arby’s instead of a trip to Hawaii.”

That said, when the boy comes home with cash, it’s perfectly fine to suggest that he save some for a long-term goal and give some away to a worthy cause.

In fact, the young man in question has already taken to handing off wads of cash to friends and strangers.

To many people, this would suggest that he’s already blessed with a generous spirit and just needs to think a bit more about how to redirect it. It might also suggest that he’s deeply uncomfortable with how much money and how many gifts he gets in the first place. His mother, however, said that his father doesn’t see it either way and wonders how they (yes, they) managed to raise a child with no respect for the value of a dollar.

“It’s classic,” Ms. Thompson said. “And very cute. Her impact is probably more than she realizes.”

But could the mother have an even greater impact? For those of you who have been in this same spot (or have seen it unfold before your eyes), what else did you try and how did it go?