Is a DIY or AI Prenup Enough for You?

Not sure whether you need a lawyer for your prenup, or whether an AI/online tool will do? Use this checklist to find out. Check every box that applies to you or your partner.

Check each box that applies:

• ☐ Either of you owns a business or has an ownership stake in a company
• ☐ Either of you has stock options, RSUs, or equity compensation
• ☐ There is a significant income gap between you
• ☐ Either of you has children from a prior relationship
• ☐ Either of you has been married before
• ☐ Either of you expects a significant inheritance or gift from family
• ☐ Either of you owns real estate (alone or with others)
• ☐ Either of you has significant debt (student loans, business debt, etc.)
• ☐ You live in one state but plan to move to another
• ☐ Either of you plans to leave work or reduce hours (for kids, school, etc.)

Your score:
0 boxes checked: A DIY or AI prenup might be okay for your situation — but read Part 2 before you decide.
1–2 boxes checked: You’re in a gray zone. A lawyer review of an AI/online draft is strongly recommended.
3+ boxes checked: You almost certainly need a lawyer involved from the start. The complexity and stakes are too high for a template.

Even if you checked zero boxes above, be aware that AI and online prenup platforms cannot:

• Give you legal advice — most platforms explicitly disclaim this and say you should consult a lawyer
• Predict how your local judge will react — enforceability depends on state law, local practice, and the specific facts of your case
• Manage the process — courts look at timing (how close to the wedding?), voluntariness (was there pressure?), and disclosure (did both sides share financials?) when deciding whether to enforce a prenup
• Negotiate on your behalf — if your partner wants different terms, AI can’t advocate for your interests
• Build a record — if the prenup is challenged years later, there’s no attorney who can testify about the advice given, the choices made, and why the deal was fair
• Provide attorney-client privilege — communications with a platform are generally not privileged

Consider full attorney representation if:

• You checked 3 or more boxes in Part 1
• You want someone in your corner who will tell you “this is a bad deal”
• You want an agreement designed to survive a challenge 10–15 years from now
• You want the process documented so a court will take it seriously
• You value peace of mind over the lowest possible price

Consider a lawyer review of an AI/online draft if:

• You checked 1–2 boxes in Part 1
• Your finances are relatively straightforward
• You want a second set of eyes but are comfortable with a template starting point

A DIY/AI approach alone may be okay if:

• You checked 0 boxes in Part 1
• First marriage for both, no kids, similar incomes, minimal assets
• You understand and accept the enforceability risk

Option	Upfront Cost	If Challenged Later
AI/Online tool only	$200–$600	$10,000–$50,000+ in legal fees if it fails or is contested
AI/Online + lawyer review	$700–$1,300	Better odds, but limited scope may leave gaps
Full attorney representation	$1,200–$2,500+	Strongest enforceability; documented process; attorney testimony available

If this checklist raised questions about your situation, we’re here to help. Whether you want us to draft your prenup from scratch or review an existing AI/online draft, the first step is a short strategy call.

Schedule a Prenup Strategy Call

Or learn more about our Chicago prenup services.