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Financial Checklist for Remarrying After 50

Love may conquer all, but it never hurts to compare finances


spinner image bride and groom figurines standing in front of their respective houses with a calculator between them
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Elizabeth Taylor did it. 

So did Zsa Zsa Gabor, Richard Pryor and Larry King.

And you might be considering it too: giving marriage more than one shot. 

Remarriage rate statistics for older adults vary but are generally high. According to Bowling Green State University’s National Center for Family & Marriage Research, 28 percent of 45- to 64-year-olds and 31 percent of those 65-plus are remarried.

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For the newly betrothed, you may think all you need is love. Yet you’ll likely also need an updated estate plan, knowledge of your Social Security benefits, and possibly a prenup before you head down that aisle. That’s because later-in-life remarriages often come with much to manage, including ex-spouses, adult kids, aging parents, and expectations based on past relationships.  

“Everyone has baggage, but the older you are and the more you’ve lived, the more baggage you have,” says Terry Gaspard, author of The Remarriage Manual: How to Make Everything Work Better the Second Time Around. 

“There are many hot-button issues” on the financial front, she says. “It can be complicated.”

Lakewood, Colorado, financial planner DeDe Jones knows that firsthand. Now 61, she remarried at age 58.  

“A prenup is, of course, a good conversation, but that just scratches the surface,” says Jones, a certified public accountant and a certified financial planner (CFP). “Daily and monthly finances need to be discussed. Who pays what, and when? Joint or separate accounts? Some of both? 

“Gifts at the holidays,” Jones continues. "Treatment of adult or nearly adult children. In-laws. Choosing who carries health insurance. Where to live. His house? Her house? Both? Neither? Hobbies and their relative cost. I could go on and on.”

But there is some good news for older lovebirds. “After age 50, people are mature enough to have proper money conversations that they weren’t ready to have in their younger lives,” Jones says. “Those conversations can strengthen the relationship and strengthen the marriage long term.”

Your checklist

If you’re thinking about getting hitched, here are the key ways to have it go off without a hitch — at least financially.

Exchange information

Head to a relaxing setting, get comfortable, then share details such as bank balances, investments and debts. Also, consider trading credit reports.

The information swap needn’t occur in one sitting, says Sara Stolberg Berkowicz, a CFP and certified divorce financial analyst. Instead, couples can opt for a series of money dates, each lasting an hour or so. “Our capacity for dealing with big topics declines after a certain period of time,” she says. “So I tell people they shouldn’t have these discussions too long.”

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Jones and her new husband made it easy to reveal financial details. They went to a coffee shop, pulled up their accounts on the financial tracker Mint and swapped phones. 

“It was awesome,” Jones says. “What a great way to get a sense of things.”

Share money-related emotions and expectations

Discuss your goals, values, risk tolerance and assumptions of marital money management. Determine how you’ll divide up financial duties, such as paying bills. Dive deep into your spending and saving philosophies, and how you feel about supporting children, stepchildren and in-laws. 

“What worked for you before may not work with the new spouse,” says Berkowicz. “You can’t just assume that you and your new or soon-to-be spouse are on the same page with these things because there’s so much diversity in the ways we handle money.”

Run the numbers

Fully comprehend how getting remarried can affect money coming in, such as Social Security and alimony. On the Social Security front, the rules are nuanced, notes Madison, Wisconsin, financial adviser and CFP Crystal Cox. For instance, if you are widowed and remarry at age 59, you could lose your survivor benefits. But if you wait until 60, you may still be entitled to benefits on your former spouse’s Social Security earnings record.

“If you get married and then discover you’ve walked away from a giant amount of Social Security, you’re going to kick yourself,” says Jones, who adds that getting remarried can also affect your taxes. “Sometimes taxes go down, sometimes they go up,” she says. “Doing some tax planning can be really important.”

Assess health insurance, life insurance and long-term care options. Review your health care plans to see how you can slash spending. In Jones’ case, she saved $5,000 a year by going on her husband’s plan. For life insurance, review policy amounts and make sure beneficiaries are up to date.

Health care is one of the top expenses for retirees. An average retired couple age 65 in 2022 may need approximately $315,000 saved after taxes to cover health care expenses in retirement, according to Fidelity Investments. So it can also be a good idea to look into long-term care insurance. 

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Revisit your estate planning documents

Review and update wills, trusts and beneficiary designations to ensure they fully reflect how you’d like to provide for a spouse and any potential children, stepchildren and grandchildren.

“Family dynamics are so interesting and different for everyone,” Cox says. “Maybe you trust your spouse enough to know they’ll get a portion of the assets and will name your children as beneficiaries. But again, anything could happen. That person could get remarried, or they could have a falling-out with your children. 

“So if you really want to make sure you’re protecting generational wealth for your children of a prior marriage, the best way to accomplish that is through trust and estate planning.”

Consider a prenuptial agreement

“I’m a huge fan of prenups,” Cox says. “They’ve gotten a really bad rap because you’re acknowledging that the possibility of divorce exists, but at the end of the day, it’s always a possibility. No one knows the future.”

So-called gray divorce rates have risen in recent decades. For instance, the divorce rate for those 55 to 64 years old climbed from five divorces per 1,000 marriages in 1990 to 12 per 1,000 in 2017, according to Bowling Green State’s research.  

Yet bringing up the idea of a prenuptial agreement can undoubtedly be awkward. If you’re wondering how to broach the topic, The Remarriage Manual’s Gaspard, who is a licensed therapist, suggests saying something like: “I was reading about prenups on the internet, and I think we ought to discuss it. We could do some research on it together and consider it.”  

Seek the advice of pros

An A-list team of experts — such as an accountant, financial planner and estate lawyer — can help you and your betrothed navigate everything from tax implications to managing retirement accounts to ensuring final wishes are met. In addition, Gaspard notes that a mediator or therapist can be a valuable resource as you wade through the emotions, expectations and decision-making that come with remarriage. 

“Nothing can make someone’s nervous system get activated in a negative way like money,” says Gaspard, who interviewed a hundred remarried couples for her book. Yet, those who have meaningful financial conversations tend to have higher marital well-being. “It’s tricky to talk about money, but it does, in the long run, benefit you,” she says.

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