The Wall Street Journal’s recent examination of ultrawealthy prenups highlights sophisticated provisions that go beyond basic asset division, including conditional payment structures often described as “trigger clauses.” These provisions activate specific financial consequences upon defined events during or at the end of the marriage. While the article notes stepped agreements that increase payouts after five or ten years and penalties for infidelity or weight maintenance, it leaves open critical questions of enforceability.

A typical trigger clause might read: “In the event of divorce following the fifth anniversary of the marriage, Party A shall pay Party B the sum of Five Million Dollars ($5,000,000), increasing to Twenty Million Dollars ($20,000,000) following the tenth anniversary.” More aggressive variants tie payments to misconduct: “If either party engages in an extramarital affair, the offending party shall forfeit all rights to spousal support and pay the other party the sum of Two Hundred Fifty Thousand Dollars ($250,000) per occurrence.” Such language must be precise; vague terms like “upon the occurrence of a significant event” invite litigation over whether the threshold was met.

Courts across jurisdictions apply a uniform framework under the Uniform Premarital Agreement Act or state analogues, requiring voluntariness, full financial disclosure, and conscionability at execution and enforcement.  Judicial treatment varies sharply by state and by the nature of the trigger. In no-fault divorce jurisdictions such as California, infidelity or “bad boy” clauses are routinely struck as contrary to public policy. The California Court of Appeal in Diosdado v. Diosdado held that a contractual penalty for adultery violates the legislative decision to remove fault from dissolution proceedings. New York courts similarly refuse to enforce provisions that effectively punish marital fault under Domestic Relations Law § 170(7). By contrast, in fault-based or hybrid states like Maryland and Texas, properly drafted infidelity clauses have been upheld when the challenging party had independent counsel and the penalty is not grossly disproportionate to the harm.

The District of Columbia has adopted the Uniform Premarital Agreement Act, codified at D.C. Code §§ 46-501 to 46-510. Under D.C. Code § 46-506, a premarital agreement is unenforceable if the challenging party proves it was not executed voluntarily or that it was unconscionable when signed and the party lacked fair and reasonable financial disclosure without a written waiver. DC became a purely no-fault divorce jurisdiction in 2024 under Elaine’s Law, creating tension with infidelity or misconduct-based trigger clauses. No published D.C. Court of Appeals decision has directly ruled on the enforceability of such provisions, leaving their validity unsettled, though D.C. Code § 46-503(a)(8) permits contracting for personal rights and obligations only if they do not violate public policy.

Lifestyle clauses dictating personal behavior, such as weight or religious requirements, are explicitly flagged as unenforceable on public policy grounds. Parties should therefore draft trigger clauses with precision, ensure robust procedural safeguards, and recognize that support waivers remain vulnerable if they would render a party eligible for public assistance at separation.

Even when a specific trigger provision is unenforceable, courts frequently sever it and enforce the remainder of the agreement if a severability clause is present. The critical inquiry at enforcement is whether circumstances have changed so dramatically since execution that enforcement would work an injustice—a standard articulated in Connecticut’s McHugh v. McHugh line of cases and codified in some UPAA variants. Provisions that become unconscionable due to unforeseen events, such as a complete waiver of support after a long marriage leaving one spouse destitute, are the most vulnerable.

Parties in drafting these clauses must therefore prioritize procedural safeguards, independent counsel for both parties, full sworn financial disclosures, and execution well in advance of the wedding—to maximize enforceability. While trigger and lifestyle clauses can provide powerful incentives and protections for high-net-worth clients, their inclusion requires careful calibration to the governing state’s public policy and case law. Overly punitive or vague language risks not only invalidation of the specific provision but collateral challenge to the entire agreement.

Refer to our Prenuptial Agreement page for more details on this subject.  We specialize in the drafting intricate enforceable agreements for high net worth clients.