Ryan Schwartz
Weddings are often approached with excitement, vision boards, and meticulous attention to details that guests will remember. But behind the flowers, music, and carefully chosen seating charts lies another reality—marriage is both an emotional commitment and a legal contract.
For many couples, the harder conversations—about money, assets, values, and what happens if things don’t work out—are avoided entirely. In this episode of the Wine and Dine Me Podcast, attorney Ryan Schwartz joins me to share what really happens when love meets legal reality, and why asking the right questions before marriage might be one of the most important decisions you ever make.
Listen to the full conversation via Spotify or Apple Podcasts.
Marriage as a Contract, Not Just a Celebration
Ryan has seen firsthand how unspoken expectations and financial misunderstandings can unravel a marriage. From his perspective, the single most important decision you’ll ever make is who you have children with—not who you marry, where you go to college, or even what you choose for a career.
“You’re entering into a lifelong connection with that person,” he explains. “Even after divorce, you’ll still see them at graduations, weddings, and other milestones. Values alignment matters, and it’s rarely discussed before marriage.”
Why Couples Avoid the Hard Questions
In my work as a wedding planner, I see clients uncomfortable even discussing event insurance—especially something like a change of heart clause, which protects deposits if an engagement ends. Ryan sees a similar reluctance in his clients.
Why the resistance?
Fear of hearing an unwelcome answer – Love can be blinding, and sometimes it’s easier not to know.
Cultural discomfort around money – Many people are raised to avoid talking about finances, even with those closest to them.
Assumption that love overrides incompatibility – In reality, mismatched spending habits, debt, or values can cause deep fractures later.
Prenups: A Roadmap, Not a Red Flag
For Ryan, a prenup isn’t about planning for divorce—it’s about setting expectations from the start.
Think of it as an operating agreement for your marriage. While it can’t predetermine child custody (that’s decided in the best interest of the child at the time), it can:
Identify which assets remain separate property.
Protect a business owned before marriage.
Clarify what happens to down payments or inherited property.
Limit or waive alimony under certain conditions.
It’s not just for the wealthy. “People with high net worth make the same mistakes as those with no net worth,” Ryan notes. “The difference is simply the scale of what’s at risk.”
The Real Cost of Divorce
While the circumstances vary, Ryan says an uncontested divorce still averages around $20,000 in legal fees—and contested cases can cost far more. Roughly a quarter of divorced couples with children end up back in court for ongoing issues.
He’s seen it all: from disputes over jointly titled homes purchased with premarital funds to battles over small business ownership. And often, the outcome could have been prevented with early, clear agreements.
Why Second Marriages Often Look Different
Both Ryan and I agree—by the time you enter a second marriage, you often have a clearer sense of yourself, your values, and your boundaries. While statistics show second marriages have a higher divorce rate, the decision-making process can feel sharper, and the tolerance for incompatibility lower.
Still, the key remains the same: open conversations before commitment.
A Call for Better Marriage Prep
Ryan believes that along with pre-marital counseling, couples should consider meeting with a divorce attorney—not to plan for failure, but to understand the legal framework they’re entering.
It’s about making the decision with eyes wide open:
Talk about finances openly and in detail.
Ask about values and life goals.
Address property and business ownership before blending them.
Document agreements to avoid ambiguity later.
As Ryan puts it: “Love is blind—but the government sees your marriage as a contract.”
Listen to the Full Conversation
This episode offers practical, sometimes surprising advice that could save couples emotional and financial strain. It’s an essential listen for anyone planning a wedding or entering a serious partnership.
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