Q. My 16-year-old son attends weekly poker nights at a friend's house in the neighborhood. He assures me that the games are friendly and that they do not play with money. He has a part-time job delivering pizzas and gets a small allowance, but he has been asking for money from me and my husband lately and I worry that he may have a developing gambling problem. How do I confront him about this topic?
A. You definitely need to address your concerns with him, and when you do, watch your attitude and approach. You don't want him to turn defensive and by doing so paint him in a parenting corner where he'll be forced to lie or turn sneaky. With that said, realize that one of the basic rules in parenting is this: Any time a child asks for money, it's the parent's right and responsibility to ask what the child will be using it for.
Getting Down to Nickels & DimesStart by scripting your own version to the following statements. Use an "I'm perplexed" Columbo-esque manner, "Something doesn't make sense here. You work and receive an allowance. It seems you should have plenty of money. I'm aware that you play poker. While you say you don't play for money, putting your request for money together with the fact that you play poker concerns me. I fear that you might be gambling your money and mine away."
Whether he's gambling for money or not, he'll probably give you a sketchy accounting of his financial situation, while adding the ridiculousness of your concerns. If he is gambling he's unlikely to fess up. Nevertheless, by bringing it up, you're putting him on notice.