my two cents

How Can I Offer My Brother Money Without Insulting Him?

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I have a question related to the dynamic of sharing money within families. My brother is a single parent of two kids and struggles a lot financially. We were raised very working-class, so no one else in my family is in a position to help him except for me. My husband and I are both attorneys and don’t plan to have children. In short, we can afford to help my brother and nephews, and would really like to do so. It sucks to watch them not be able to do after-school programs and other enriching activities that my brother can’t pay for. 

The problem is, my brother is very proud and might be insulted by the offer. Our extended family often makes comments about how my husband and I think we’re better than them because we have fancy jobs and live in a major city (which I try not to perpetuate), but it makes me worried that offering help could be taken the wrong way. How can I be helpful and sensitive to what they need, without hurting our relationship? I’m hoping to talk to him about it during the holidays this year.

You could start by telling your brother exactly what you’ve said here — you want to talk to him about family finances, but you’re nervous about how he’ll react. I’ve found that when I begin a tricky conversation with an acknowledgment that the topic is awkward, it lowers everyone’s defenses and creates a more open dynamic. Honesty can be disarming.

Meanwhile, you may want to hold off until after the holidays. “This season can be wonderful, but it’s also an intense and complicated time,” says Ellen Perry, the founder of an advisory firm that specializes in family finances. “From a logistical standpoint, I wouldn’t recommend bringing this up during a family gathering or other high-stakes moment.”

Instead, Perry suggests waiting until the post-holiday dust has settled. “Then you can broach the topic by saying something like, ‘I’ve been thinking a lot about you and your kids, and I’d like to find a way to be more helpful to you financially. But I want to do it in a way that’s sensitive to your needs. Can we have a conversation about that sometime soon?’” That puts the ball in his court to start the discussion when he’s ready.

From there, lead with your intentions, says Traci Williams, a financial therapist based in Atlanta. For instance: “You’re doing such a great job as a father, and we want to support you and the boys in a way that’s most valuable to you.” You can also say what you don’t want — to hurt his feelings, to make him uncomfortable, to step on toes or meddle in his parenting decisions. You should also be clear that both you and your husband are on the same page about this (and obviously, make sure that is the case beforehand).

Then offer some suggestions for what you could do, and ask for his opinion. “Emphasize your brother’s involvement in the process,” adds Williams. “You want him to play an active role.” Here are some ideas: You could open a 529 account to fund your nephews’ education. You could give your brother cash (any amount up to $16,000 is tax free, but more than that will be subject to gift tax). You could pay for specific things like tutoring or camp or medical bills.

Giving money to family members is inherently fraught because it can create a power imbalance. One way to keep that in check is to make sure it really is a gift. That means no strings attached, no favors owed, and no snide remarks. A lot of family members pay for stuff and expect certain things in return — a say in where their money goes, a visit at Christmas every year. Conversely, the person on the receiving end might start asking for more things that you aren’t willing to give. This is where things go sour.

Luckily, you can avoid those minefields by being extremely clear about how much you can contribute and when. If this is a onetime thing, say so: “We have some extra cash this year and would love to give it to you and the boys. We may not be able to do this again, but we want to help you out as much as possible.”

You should also do your best to check your judgments at the door, adds Perry. “I see parents do this all the time — they give their kids money, and then their kids go on a lavish vacation or quit their jobs. And the parents are like, ‘Wait a minute. That’s not what I expected, and I don’t approve.’” That said, if you don’t entirely trust your brother with finances, or you’re nervous that he’ll use the money to pay for something that goes against your values, then you should establish stronger parameters up front (e.g., you’ll pay for education or certain activities).

Finally, it’s still important to do things to maintain or strengthen your relationship with your brother beyond your financial support. If you live nearby, you could take them out to breakfast once or twice a month; if you live farther away, you could visit and watch the kids for a weekend to give your brother a break from parenting (the ultimate gift).

Your brother and his kids are clearly lucky to have you. But the point of your generosity is that you’re lucky to have them — they obviously mean a lot to you. This relationship is a two-way street, and the more you communicate that, the better this conversation will go.

The Cut’s financial advice columnist Charlotte Cowles answers readers’ personal questions about personal finance. Email your money conundrums to

How Can I Offer My Brother Money Without Insulting Him?