I still recall an impactful conversation that took place several years ago, shortly after my book was published. While attending a community luncheon, I was seated at a round table with several couples. We exchanged pleasantries over salads and iced tea, and then one woman across from me suddenly lit up.

“Oh, I know you! I saw your picture in the paper,” she said. “You’re the one who wrote that financial guidebook for widows, right?”

I nodded, smiling. She waved her hand and laughed. “But I’ll never need it. You see, Bill and I have an agreement. I get to die first.”

The whole table chuckled. She continued, with a wink toward her husband, “He handles everything with the money. I don’t bother with any of that stuff – it’s boring. I’d rather spend time with the grandkids. He’s so good with our finances. I don’t need to get involved.”

She even covered her ears playfully and added, “When he tries to explain something, I just go ‘la-la-la-la!’”

Bill smiled politely but looked a bit weary. And noticeably older.

Here’s the thing: statistically, women outlive men by about seven years. So, when Bill dies first – as is likely – his wife will be left not only grieving his loss but also navigating their finances alone for the very first time.

And that, my friends, is what I call magical thinking – the belief that if we don’t talk about hard things, they won’t happen.

But guess what? Someone in every couple is going to die first. That’s a fact. And no amount of ‘la-la-la’ will change it.

Painful Memories and Avoidance

As we continued talking, I gently asked this woman, “Does it always work out in your family that the wife goes first?”

There was a long pause. Then she admitted, “Well, no. My mother was widowed, and it was really hard on her. I just don’t want to go through what she did.”

Bingo!

Sometimes avoidance isn’t about laziness or indifference – it’s about fear. This woman wasn’t flippant; she was frightened. And understandably so. Watching a parent struggle after losing a spouse can make anyone want to bury their head in the sand.

But fear doesn’t prevent loss. It just makes us less prepared when it comes.

Real Talk Over Dessert

After a bit more quietness around the table, another woman chimed in: “When my friend’s husband died, she was a mess. She didn’t know a thing about their finances. It was overwhelming.”

Back to the original speaker: “Exactly! That’s why I want to go first!”

At that point, I gently asked one more question, “Do things in life always turn out the way we wish they would?”

She didn’t answer out loud. But her expression changed. I could almost hear the inner monologue: “No, things don’t always go how I want. And the idea of being alone, without Bill – it terrifies me.”

That’s when Bill quietly said, “See, Jane? We really do need to talk about this.” He’d clearly tried before. Then he asked how they could get a copy of my guidebook. I passed him my card. And Jane took it, too.

Moments later, we all turned our attention to the most pressing decision at the table – raspberry cheesecake or chocolate cake?

Love Means Planning Together

Here’s what I believe: one of the most loving gifts a couple can give each other is a mutual understanding of their financial world, before a death or crisis happens.

Don’t wait until one of you is gone to untangle the web of accounts, documents, and decisions. Have the conversations now, while both of you are healthy and clearheaded. Start with simple but essential questions, including:

• Do we both know where the important documents are?
• Are our wills, trusts, and powers of attorney up to date?
• Who are the beneficiaries on our IRAs, annuities, and life insurance policies?
• Where do we keep our account passwords and PINs and are these organized?
• Do we both understand how our retirement income works?
• Who are our professional advisors, and how can they be contacted?

I often recommend creating a “household manual” – a centralized place where this information is kept and easily accessible. That might include everything from financial information to contact details for your trusted plumber and handyman.

A Gentle Conversation Starter

Bringing these topics up doesn’t have to feel grim. In fact, it can be a heartfelt gesture.

Try saying something like, “Honey, because I love you so much, I want us to go over our finances together. If something happens to one of us, I want the other to be okay.”

If you’re the “Jane” in your relationship – the one who’s opted out of money matters for years – it’s never too late to start learning. You don’t need to become a financial expert. You just need to be informed enough to step in with confidence if the time comes.

You Deserve to Be Prepared

I’ve worked with hundreds of widows over the years. I’ve heard heartbreaking stories from women who never saw the bills, never logged into the bank account, never once met the financial advisor – and suddenly, they had to figure it all out alone.

But I’ve also seen the opposite. Widows who told me, “Thank goodness we talked through this before he passed. It made all the difference.”

I know that talking about death and money can feel uncomfortable. But your future self – and possibly your future widow self – will be forever grateful that you did.

Because magical thinking might feel easier in the moment. But real planning? That’s true love in action.

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“On average, women outlive men by about 7 years. Planning ahead is not pessimism – it’s empowerment.”

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Let’s Have a Conversation:

Have you and your partner talked about your financial plans and preparations? Do you know where your important documents are kept? Have you experienced (or witnessed) the consequences of avoiding these conversations? What’s one small step you could take this week to be more financially informed or prepared?