After Loss, Love Again

I belong to a club I never wanted to join: women who have outlived their husbands. Like me, millions of baby boomer women, and now Gen Xers too, will face life without their long-term partner.

Thankfully, today’s widows have more choices than our great-grandmothers did. Some of us embrace living solo. Others are surprised to find companionship again, sometimes even love. That next chapter can be sweet, but it’s also financially complex.

I know this firsthand. Eleven years after my husband died, I remarried at age 71. But before saying “I do” again, my new husband and I worked through a host of financial and emotional questions—just like the ones I now offer below.

Money matters more than you might think. A LearnVest survey found that financial issues are more than twice as likely as sex to cause tension in a relationship. Talking honestly about money isn’t just smart—it’s essential.

In a study I co-led of over 4,000 widows from around the world, nearly one-quarter had re-partnered—through marriage or long-term relationships. What was their most significant piece of advice? Take your time, talk honestly, and don’t overlook the money questions.

Here are 10 to get you started:

1. Have you and your new partner had a discussion about financial matters yet? It’s tempting to avoid tough topics early on, but clarity builds trust.
2. Who pays for what? Will you split expenses according to an agreed-upon method? Use a joint account? Keep finances separate?
3. Where will you live, and whose name is on the deed or lease? Moving in together is exciting, but it’s worth considering the legal and financial implications.
4. Will you sell your home or keep it? If you sell, who gets the proceeds? Will you buy something together?
5. What are your partner’s retirement plans? Do you both want to travel, volunteer, or downsize? And can you afford it?
6. Will you merge investments or keep them separate? Financial independence can be healthy, but transparency is essential.
7. What if your partner earns far less or has more debt? Have you considered whether your partner’s net worth is significantly different from yours? Be honest about expectations and boundaries.
8. Have you discussed healthcare needs and costs? Illness or caregiving roles can come suddenly. Will you support each other?
9. What are the financial responsibilities for children or aging parents? Love might be free, but families may bring financial obligations.
10. Have you considered a cohabitation or prenuptial agreement? These conversations may protect both you and your loved ones.

Here’s what some real-life widows shared with me during our research:

“I didn’t bring up the money stuff because I thought it would hurt our relationship . . . We split up later anyway over the money.”

“Be careful with your finances. Don’t allow anyone to take advantage of you because you are lonely or sad.”

“Understand each other’s financial stability and responsibility. Don’t wait to be surprised later that your partner has huge credit card debt!”

You’ve already walked through grief. If you’re fortunate enough to love again, protect your heart and your wallet. Don’t rush. Ask the right questions. And if it feels too overwhelming, a trusted and skilled professional, especially one familiar with widowhood, can help you navigate the journey with clarity and compassion.

Starting the Money Talk

Don’t try to cover everything at once. Begin gently. A good opening might be, “I’ve been thinking about my financial future. I’d like the two of us to talk about that as we look toward our future together.”

Choose a relaxed time when you’re both comfortable, such as Sunday evening after dinner. Keep your first conversation short, around 30 minutes. Tackle just one or two questions. Then try another talk next week. This slow approach can reveal what matters most to each of you—and whether you’re truly financially compatible.