It’s been a love story for nearly three years, and now Taylor Swift and Travis Kelce may be entering their most romantic era yet: asset planning. With Swift reportedly worth $2 billion and Kelce bringing his own Super Bowl-sized fortune to the table, the question is not whether there will be champagne problems—it’s how they will sort out what stays “mine,” what becomes “ours,” and what happens if there’s a break-up.

Enter the prenup. It may not sound as swoony as an Instagram engagement post, but for a couple with music catalogs, real estate, endorsement deals, and probably several lawyers on speed dial, a prenuptial agreement is less planning for the breakup and more “you need to calm down, we handled this.” For Swift and Kelce—and, honestly, for plenty of non-billionaire couples too—the hard conversations about property, taxes, privacy, and support are often easier before the wedding than after everything has changed.

I’ll be honest: I don’t have a prenup. When I got married, I didn’t have much other than a mountain of student loan debt and dreams of becoming a tax attorney. My husband had a few more dollars in his pocket than I did, but hardly anything that we felt like we’d ever need to sort out. It all felt so simple. Years later, we have three kids, some real estate, a business, and a set of Nick and Nora glasses that we both feel pretty strongly about. It’s not so simple now.

Lance Nelson, a partner at Chester County, PA-based MacElree Harvey who practices family law, says that while previous generations might have married soon after college—when income was relatively low, and debt may have been high—the current generation is taking a page from Swift's playbook and waiting until their careers are established before marrying. Millennials and Gen Z seem to get it. They're entering marriage not starry-eyed but clear-eyed—less Fearless-era Swift, more Midnights. Nelson adds that these couples have something the previous generation did not: access to the internet. They know what it can look like when things can go horribly wrong and are more likely to discuss ways to protect themselves and their families in advance.

Prenups can help settle important issues like the distribution of certain assets, but they are not a substitute for thoughtful tax and estate planning—or for advice that accounts for the right jurisdiction. That’s important because family, property, and inheritance rules do not always travel neatly across borders.

For Americans abroad, tax and estate planning can come with a plot twist: the U.S. may not get the final word. In many civil law countries, forced heirship rules reserve a portion of an estate for certain family members—often children or a surviving spouse—regardless of what the decedent’s estate plan says. That can create real problems for familiar U.S. planning strategies. And because these rules may apply based on where a person lives or owns property—not just citizenship—globally mobile families should not assume that a U.S. estate plan will travel neatly across borders.

And speaking of getting the right help: AI can be a terrific tool for organizing information and helping you think through the questions to ask. But when the issue is legal advice—especially around money, marriage, taxes, estates, or confidentiality—it is not a stand-in for a lawyer.

That was the finding in a securities fraud case, in which a New York federal judge ruled that a criminal defendant’s conversations with the AI platform Claude about potential defense strategy were not protected by attorney-client privilege or the work product doctrine because the chatbot was not an attorney. Although the ruling came in a criminal case, the same reasoning would likely apply in civil matters as well—including disputes........

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