My Brother’s Keeper

I have a younger brother who means the world to me, and I think he's about to make a big mistake. He's been dating a girl for nearly a year, living with her for half that time, and they seem ready to take that matrimonial step. Normally, this would be a joyous occasion, but she is six years older than him, and I suspect she's pushing him on this and, more importantly, they don't get along very well (in fact, they have already started going to couples therapy). My gut says that he needs to get out of this relationship, but he tells me that he's happy about 75 percent of the time. I don't feel like I'm "right" about this enough to very aggressively share my point of view, but I also think he's a great guy and deserves much better. Help me!

Older Brother

First, OB, you need to accept the possibility that this might be a happy relationship for your brother. Being happy 75 percent of the time doesn’t sound very good to me, but maybe he’s satisfied with that or not very good with numbers. Second, you need to accept the possibility that he may get married, and it may end badly no matter what you do. And third, know that he’s not going to make a clean break from this relationship. It may feel like your goal is to get him to see this situation clearly and then get out immediately, but that’s not your aim. You’re playing a long game here—you want him to have a happy life. How to help with that?

It is often almost physically irresistible to tell your sibling everything he or she should do, exactly how to do it and why. It is also all but useless. Those little devils have minds and hearts and lives of their own, and they don’t respect the experience and wisdom of their older siblings’ extra years.

In a non-confrontational moment, tell your brother that you have some questions. Ask him if he ever thinks about an easier and happier relationship. Is he thinking about marriage? Does he have any reservations about marriage? What does the couples therapist say about their relationship and marriage plans?

Now, here’s the part that’s really difficult for older siblings. You have to let him talk. No matter what he says. The less you say and the more he says, the better. When it sounds like he’s finished talking, start counting in your head, backwards from 10, and wait for him to start talking again. Your goal is to let him arrive at whatever conclusion he arrives at. He’s inside of this relationship right now, and he will push back against any attack on it or her. You’re trying to give him space to voice any doubts he might have, and he probably won’t do that if he thinks you’re going to pile on. Remember, long game. They may get married, and it may go sour. If that happens, or if something worse in his life happens, you want him to think of you as someone he wants to talk to about it.

Christmas Cash

As a child, I was given a very pretty doll, but I was a little too old to play with it. I kept it for 22 years and finally decided to give it to my 7-year-old niece for Christmas this year to try to save a little money and share something nice from my past. My niece picked up the doll and immediately dropped it back in the box, uninterested. (Her mom, my sister, had warned me she wasn't that into dolls, but I thought I'd give it a try.)

Only a few weeks after Christmas, a friend mentioned that that very doll has become a collector's item and similar ones were selling for $1,000. I immediately called my sister and told her the situation. My sister assured me the doll has stayed in the box since Christmas. My sister asked if I'd like the doll back. I said for now, please just preserve it and we'll decide later what to do. My preference is to take it back and sell it if I can get a good price. But it feels rude to take a gift back. I would, of course, get my niece a replacement gift (though she would never know the doll was gone). 

What is most appropriate? Should I offer to use the profit for the benefit of my nieces and nephews? Or maybe half of it? I am in debt, and my financial situation is such that $1,000 is quite a lot of money.

Regretful Regifter

Ouch. In trying to save a little money, you ended up giving away $1,000. (And I would say $1,000 is quite a lot of money, period.) Let’s look at this in order, from the most superficial level, gifts, to the deepest: relationships with family and money.

In general, a gift is a gift. To ask for it back seems to say, “I intended to give you something, but certainly not something this nice, and I want it for myself. Can I please have it back?” If this were someone you weren’t particularly close with, like the child of a work acquaintance, I’d say you were stuck. But, fortunately for you, it was the child of your sister, so there’s hope.

You need to assess your relationship with your sister. Are you close enough that you’re comfortable asking her if you can sell the doll? You also need to consider your relative financial situations. You indicate that money is tight for you. Is that the case for your sister? If your relationship with your sister is close and open and happy, I’d suggest asking her if you can buy your niece another gift, sell the doll, and split the money. Half for you, half for your niece’s college fund. That’s a nicer gift than anyone expected you to give the niece and a better choice for her educated, feminist, financially secure future.

Before you rock the boat at all, though, you need to do a little eBay-based research. A vague notion that “you can make a lot of money selling stuff on the Internet” has permeated our culture (helped along by exceptional success stories, The 40-Year-Old Virgin and shows like “Antiques Roadshow”). And sometimes you can. But, like most things that promise quick and easy riches, the actual situation is often a little less lucrative. So, check it out before you have this conversation with your sister.

You’re probably thinking that this is a good point for me to stop talking, and you’re right. I am working very hard to restrain myself from veering into financial advice. See, you mentioned debt and then you mentioned a potentially valuable collectable you had sitting around, and I want you to have an aggressive plan to pay down your debt. But, it seems the height of poor form to acquire an advice column and still somehow manage to offer unsolicited advice. When you’re ready, write again and we’ll talk about money.

Got a question? Email Rhonda: [email protected]