Broken promises threaten to create a disconnect between mother and son.

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Dear Prudence:
I'm engaged to a wonderful man with two boys. The mother lives in another state and rarely sees the children. The oldest will turn 10 soon, and his mother promised him a cell phone for his birthday. He has asked us for one in the past, but his father and I have told him that he's too young and that we will get him one when he turns 15. Since his mother promised him the cell phone, it has been all he can talk about. He's picked out which phone he wants and has started collecting phone numbers to add to his phonebook. Recently, she informed my fiance that she will not be getting him the cell phone because she cannot afford it. She has not told her son yet and refuses to do so. My fiance and I don't want to have to break the bad news to him ourselves. We feel she is the one who made the promise, so she needs to inform him. I've covered up for her in the past by following through with promises she has made, but we are not going to cover this one. What is the best thing that I can do so that he doesn't get hurt by his mother?

—Stepmom to Be

Dear Stepmom,
Both boys are going to get hurt by their mother over and over. She'll neglect her sons, then she'll get their hopes up, then she'll crush them. I frequently get letters from people who grew up with mothers like this. They write that their mothers are old and lonely and are begging for their love and attention; but long ago they learned to harden their hearts to their mothers and now don't have any love to give. The boys' father and you must do what you can to provide a powerful counterbalance by being loving, consistent, and reliable parents. You don't have to cover for this woman, but since she doesn't even have the fortitude to acknowledge she's made another botch of things, you're going to have to explain. In this case, the father should tell his son that his mother really did want to get him the cell phone, but then she realized she doesn't have enough money. He can say the right thing for the mother to do would be to tell him herself, and it's too bad she's so sad and ashamed that she can't bring herself to do it. It will be tempting to demonize her to the kids, but you have to stay as neutral as possible while also letting them know that you understand how painful it is for them to be disappointed by her. Please plan a great birthday party for this boy. And while I agree a 10-year-old is a little young for a cell phone, if you can afford it, you will find in a year or two it's actually a useful way to keep track of a kid with lots of friends and activities. So consider promising him a phone when he's 11 or 12. Since it will be a promise coming from the two of you, he'll learn that there are adults who actually keep theirs.

—Prudie

Dear Prudence Video: Harassed at the Gym

Dear Prudence,
I am dating a good, kind man who treats me well, but one small issue has come up. We typically split the check when we go out to dinner (at his suggestion, but this is fine with me), although occasionally he will pay (once every four weeks, say). However we have fallen into a habit where he visits me at home two or three nights per week, and I cook nice dinners and serve beer, wine, chocolates, etc.  I enjoy being generous with my loved ones, and it normally wouldn't cross my mind to expect anything in return. However, this weekend brought the inequity of the situation to my attention, as I made a lovely dinner and we drank a couple of bottles of wine. This probably cost me about $70 to $80. When we went out to lunch the next day, the bill was $42, and he said, "I'll put in $20." I certainly don't mind paying my share, but I've realized it is probably cheaper for me to go out, as I pay for both of us at home! He is employed, and I am a stay-at-home single parent, so this can't really go on. How can I raise this issue without being critical or demanding?

—Stiffed

Dear Stiffed,
I had a good, kind, successful boyfriend just like yours. We always split the check (even when he ordered a bottle of wine, I had a single glass, and he polished off the rest). He did treat me to a well-reviewed restaurant for my birthday, but when he saw the prices on the menu, he declined to order dinner and spent the whole evening with his fork poised over my food, begging for a bite. Pathological cheapness can be intractable, and you have to decide if it's going to be a deal-breaker for you. But before you get angrier and angrier at this "small issue," you need to bring it up with him. Explain that you're on a tight budget and that, while you love to cook nice meals for him in your home, between that and meals out where you pick up at least half the check, you're going broke. You can say you recognize he is cheap—ah, I mean frugal—but you need more equity in your spending. Don't allow him to establish a running tab on your expenditures so he can show that things are even—another gambit of the tightwad. Explain that a calculator kills the sense of generosity with each other that's needed in a healthy relationship.