Is There a Not-Awkward Way to Ask My Parents About Their Wills?

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Mary, 31, is in grad school and will be paying student loans for what feels like the rest of her life. Meanwhile, her parents — who are divorced and in their 70s — are both well-off and have mentioned in the past that certain things will “go” to her someday. They’re not a family that really talks about money, and she feels uncomfortable bringing it up or asking about further details. Still, it would help her a lot to know, especially if it might affect her loan payments or what kinds of jobs she’ll pursue. At the very least, she would like to make sure that her parents (again, especially her dad, who is single and not in the best health) have a sound estate plan in place. How can she bring this up with them without making it awkward, or alienating them, or appearing selfish and greedy?

You’re nervous to ask your father how much cash you’ll gain when he kicks the bucket? What could possibly go awry in that conversation? At the very best, it’ll remind him of his impending mortality — a turd in the punch bowl, by anyone’s standards — and at worst, he’ll perceive you as an opportunistic money-grubber. He could even decide that he doesn’t want to leave anything to you anymore, at all. Off it goes to the orca whales or your annoying second cousin or a political candidate you despise.

That’s an extreme scenario, but put yourself in your parents’ shoes, says Amanda Clayman, an L.A.-based financial therapist. “Almost all families that I’ve encountered have a lot of worry about inheritance. From the older generation, there’s a sense of, ‘This is my money. This is not your future money,’” she explains. “Parents don’t want their children — their heirs, if you will — counting that money, and judging them for how they manage or spend it before passing it on. It can make them feel like others are waiting for them to die. And that may not be the case, but when they hear questions about wills, they project that their passing is anticipated.”

Conditions can get particularly fraught towards the end of one’s life. A few years ago, a relative of mine was diagnosed with an aggressive cancer and immediately went out and bought a convertible with all the bells and whistles. When her concerned daughter told her she was being reckless, she became furious — she was still alive, dammit, and planned to enjoy her final days as she pleased. Their fights continued right up until the end.

So how do you open the floor in a productive way? “Begin with very general questions,” says Clayman. “It’s much safer, and lays the groundwork for more explicit communication down the road. Are your parents okay, financially? Is there anything they want you to know, and anything they want to know about you? Do they have a plan in place? If anything were to happen, are their accounts and passwords in a place where you would be able to access them, if need be?” She recommends organizing your thoughts and coming up with a list of questions beforehand; if you don’t know where to start, you can find examples and checklists on websites about caring for aging parents.

Meanwhile, embrace the awkwardness; you aren’t gabbing about the weather. “Allow yourself to be embarrassed,” Clayman continues. “Let your feelings be out there. You can say that you hate to ask these questions, but that it’s something you worry about, and you dread this day but you don’t want it to be any harder than it will be.”

Conversely, your parents might be relieved that you’re bringing this up — and don’t be surprised if they think you’ve talked about it before. A 2016 survey by Fidelity found that that 69 percent of parents believed they had discussed their wills and estate planning with their children, but only 52 percent of kids in the same families said they had. The same study showed a yawning disparity between parents’ expectations from their kids, in terms of executing estate plans and late-in-life financial planning, and what their kids felt was expected of them (parents expected their kids to be involved, and kids didn’t think their parents wanted them to be). These miscommunications might be due to people pussyfooting around genuinely uncomfortable topics; your dad might think that a few post-Thanksgiving dinner sentences counted as a “discussion,” whereas you were in a pie coma and don’t even remember. It’s worth getting on the same page (actually put your points in writing, if you can).

But it’s not enough to make sure that your parents have an estate plan in place; make sure to account for whatever special soup of relationship dynamics your family happens to serve up. My friend Martha, for example, made sure to ask her dad about putting an executor in place for his will, because she wants a third party to handle her sister, whom she doesn’t trust. Stepparents can also be tricky; if there’s no will in place when a person dies, their stuff usually goes directly to their spouse, according to most state laws.

On that note, see if you can avoid the need for collective decisions. My friend Alicia learned this the hard way: Her grandmother died almost five years ago, leaving behind a sizable estate to be divided up among her relatives, but Alicia’s uncles can’t agree on how to move forward. “We can’t do anything without everyone’s signature, so we can’t sell my grandmother’s house, which is just sitting empty, depreciating in value,” she says. “I don’t know when and how it will get resolved, but right now, there’s just a bunch of money sitting in an account somewhere, doing nothing. And my grandma would be so pissed. She would want us to have it, and do cool things with it.”

Which brings me to the hardest part: Managing your own expectations about what’s coming your way. The promise of inheritance, however vague, is like knowing that you will get a winning lottery ticket at some point in your life, but not when or for how much. It’s understandable if you’ve been carrying a dim torch of hope in the back of your mind for this windfall to magically cover your bills, but you’ve got to live your life as though it won’t. “The best thing you can do is get healthy, emotionally and financially, in and of yourself so that you are not dependent on what other people are going to do,” says Clayman.

How Do I Ask My Dad About His Will Without Being Awkward?