Penalty Clauses, Cheating Definitions, and the Limits of What a Prenup Can Actually Do

By now you may have seen the clip of Bill and Giuliana Rancic on their new podcast, laughing about the prenup that never quite got signed before their wedding. The story is charming: Bill asked her to sign a prenup. Giuliana told Bill she was happy to sign, negotiations went back and forth between legal teams for weeks, and Bill eventually discovered that Giuliana's attorney was her older brother, who had never once opened a law textbook. The prenup did not get signed. Twenty years later they are still together and seemingly very happy about it.

What caught my attention though, was not the unsigned agreement. It was Giuliana’s demand for a 110% cheating clause, the penalty Giuliana apparently wanted built into the prenup that would have required Bill to pay her 110% of his net worth if he was caught cheating.

Can an attorney draft that? Yes. Will a judge enforce it? That is a much more interesting question.

The Practical Problems Start Immediately

Before we even get to enforceability, the logistics of a penalty clause like this raise questions that require much thought. How do we determine a person’s net worth in this circumstance?  Is all of his net worth marital property, a portion of which Giuliana would already be entitled to? Where does the extra 10% come from? How is that extra 10% going to be paid?  And from where, exactly? Venmo?

And then there is the definitional problem, which is arguably more complicated. How is cheating defined?

In Pennsylvania, traditionally, proving infidelity in a legal context generally requires evidence of a physical sexual act. But we live in a world of considerably more nuance than that standard anticipates. What about an emotional affair? Sexting? A subscription to someone's OnlyFans? A relationship that is emotionally intimate but never physically consummated? The list of edge cases is long, and the legal framework for evaluating them is not nearly as clear as the people drafting penalty clauses tend to assume.

These are not hypothetical problems. They are the questions that would need to be answered in a courtroom if a penalty clause were ever invoked, and the answers are not always the ones the person who dreamed up the clause had in mind.

Just Because It Is Drafted and Signed Does Not Mean It Is Enforceable

This is the part that surprises people most. A prenuptial agreement is a contract, and in Pennsylvania it is analyzed under contract law rather than a fairness standard. That means courts are looking at whether the agreement was validly formed, whether both parties had adequate disclosure of the other's financial situation, and whether the terms violate public policy.

Penalty clauses tied to behavior, including infidelity clauses, are among the provisions most likely to face scrutiny. Courts have discretion in how they interpret and enforce these terms, and what felt like a reasonable consequence during a prenup negotiation may look quite different to a judge reviewing it years later in the context of an actual divorce proceeding.

The gap between what a couple agreed to and what a court will actually enforce is real. It is not a reason to avoid prenups. It is a reason to work with an attorney who understands where that gap tends to appear and how to draft agreements that are more likely to hold up.

When a Prenup Starts to Drift From Financial Planning Into Behavior Regulation

The infidelity clause is one of the more common places where prenups start to expand beyond their intended purpose, but it is not the only one. Over the years, prenuptial agreements have been drafted to include clauses about social media behavior, substance use, weight, intimacy frequency, and even where a couple will live. People can and do ask their attorneys to include these things, and attorneys can and do draft them.

But this is where the purpose of the document gets lost.

A prenuptial agreement is a financial planning tool. Its core function is to establish, in advance of marriage, how assets and obligations will be handled in the event of divorce or death. It exists to give couples control over decisions that state law would otherwise make for them, and to do so at a time when both people are thinking clearly about the future rather than managing the fallout of the present.

When a prenup becomes a list of penalties and behavioral requirements, it starts to look less like financial planning and more like an attempt to regulate what the marriage looks like. Those are different documents with different purposes, and conflating them tends to produce agreements that are harder to enforce and harder to live with.

Prenups are not intended to be about punishment. The ones that hold up and actually serve the people who signed them tend to be the ones that stayed focused on finances.

What Bill and Giuliana Actually Got Right

Here is the thing about the Rancic prenup story that does not get enough attention: they had the conversation. They negotiated and went back and forth between “legal teams” for weeks. The process generated productive discussion about expectations, finances, and what each person wanted going into the marriage.

That conversation is valuable, and most couples never have it.

The problem is that a conversation is not an agreement, and an unsigned agreement is not enforceable. When the Rancic's married without a signed prenup, they married under the default rules of whatever state law applied to their situation. Those rules do not account for what they discussed, what they negotiated, or what either of them believed they had agreed to. If it had ever gone sideways, the law would have told them what their prenup was, whether they liked those terms or not.

The conversation is the first step. The signed document is what makes it real.

A Final Thought

A well-drafted prenuptial agreement is one of the most honest and productive conversations a couple can have before marriage. It requires both people to think clearly about finances, about what they are each bringing into the marriage, about what they would consider fair if things did not work out, and about what they want to protect for the people they love.

Done well, it is not about anticipating failure. It is about making intentional decisions together at a time when both people are thinking about the future with clarity and goodwill. That is a reasonable thing to want, and it is worth doing right.

Just maybe leave the 110% penalty clause out of it. And definitely do not hire your brother as legal counsel.