15 Essential Questions Before You Say “I Do”
Prepared by Steve Benmor, B.A., LL.B., LL.M.
Certified Specialist in Family Law
Benmor Family Law Group
Why This Checklist Matters
Whether you’re entering a second marriage with established assets, blending families, or starting a new chapter later in life, getting married is both an exciting milestone and a significant legal and financial partnership. While no one enters marriage expecting it to end, having honest conversations now can protect both partners and prevent costly conflicts later.
In Ontario, married spouses who separate are required to equalize assets accumulated during their marriage and equally share the net value of a matrimonial home. A well-drafted Marriage Contract (prenup) allows you to define your financial arrangements on your own terms, rather than leaving it to default legal rules.
This checklist will help you start the important conversations that every couple should have before marriage—whether you’re established professionals bringing significant assets into the relationship, business owners protecting family enterprises, or couples receiving family financial support for your future together.
PART 1: FINANCIAL DISCLOSURE
1. What assets does each person currently own?
Why it matters: Full disclosure is legally required for a valid Marriage Contract. List everything: real estate, vehicles, investments, RRSPs, TFSAs, business interests, valuable collections, and intellectual property. Hiding assets can invalidate your entire agreement.
2. Do either of you have children from previous relationships, and how should their inheritance be protected?
Why it matters: Second marriages and blended families require balancing fairness to your new spouse with protecting your children’s financial future. A Marriage Contract can ensure your estate plan aligns with your wishes, prevent family disputes after you’re gone, and provide clarity for everyone involved. This is especially important when children from previous relationships expect to inherit family property, business interests, or other significant assets.
3. What is each person’s current income and earning potential?
Why it matters: Income differences affect contributions to household expenses, savings goals, and potential spousal support obligations if the marriage ends. Being transparent about career trajectories and income expectations sets realistic expectations.
PART 2: PROPERTY & REAL ESTATE
4. Who will own the matrimonial home?
Why it matters: Under Ontario law, the matrimonial home receives special treatment. Even if one spouse owned it before marriage, the full value (not just the increase) gets equalized. A Marriage Contract can address this differently.
5. If one person owns property before marriage, how should it be treated?
Why it matters: Pre-marital property can be protected in a Marriage Contract. Without one, generally, only the increase in value of most assets, including property, during the marriage is typically equalized. If family money helped with the down payment, this should be documented.
6. How will we handle real estate purchased during marriage?
Why it matters: Will property be owned jointly or separately? Who contributes to the down payment? How are mortgage payments split? These decisions impact both ownership rights and tax implications.
PART 3: INHERITANCE & FAMILY WEALTH
7. Are inheritances expected from either family?
Why it matters: In Ontario, inheritances received during marriage and kept separate are not equalized—but only if properly segregated. Mixing inherited funds with joint accounts can eliminate this protection. A Marriage Contract can provide additional clarity.
8. Has either person received significant gifts or financial support from family?
Why it matters: Family contributions toward a home purchase, business startup, or education may come with expectations. A Marriage Contract can protect family gifts and clarify whether they’re loans or gifts.
9. Are there family businesses or trusts involved?
Why it matters: Business interests and trust assets require special consideration in a Marriage Contract. Without proper planning, the value of a family business may be subject to equalization, potentially forcing a sale.
💡 Realizing you need expert guidance to protect complex assets? A professionally drafted Marriage Contract ensures your business, family wealth, and children’s inheritance are properly protected.
PART 4: BUSINESS INTERESTS & CAREERS
10. Does either person own a business or professional practice?
Why it matters: Business owners face unique risks in divorce. The value increase in a business during marriage is typically subject to equalization. A Marriage Contract can protect business assets and prevent an ex-spouse from claiming ownership interest.
11. Will one spouse take time away from their career (for child-rearing or other reasons)?
Why it matters: Career interruptions impact earning potential, pension contributions, and long-term financial security. A Marriage Contract can address compensation for career sacrifices and ensure fairness.
PART 5: SPOUSAL SUPPORT & DIVISION OF ASSETS
12. What are our expectations about spousal support if we separate?
Why it matters: Without a Marriage Contract, spousal support is determined by factors including length of marriage, income disparity, and roles during marriage. You can agree to limit or waive spousal support (though courts may override this in cases of hardship).
13. How should we divide assets if we separate?
Why it matters: Ontario’s default rule is 50/50 equalization of net family property accumulated during marriage. A Marriage Contract allows you to agree on a different division that reflects your unique circumstances and contributions.
14. What happens to pensions and retirement savings?
Why it matters: Pensions and RRSPs accumulated during marriage are subject to equalization. If one spouse has a significantly larger pension, this can result in a substantial transfer of wealth upon separation.
PART 6: PROTECTING YOUR AGREEMENT
15. Have we both received independent legal advice?
Why it matters: For a Marriage Contract to be legally binding and durable against future challenges, it is the industry standard and highly recommended that both parties receive Independent Legal Advice (ILA) from separate lawyers.
While technically not an explicit requirement under the Ontario Family Law Act, ILA is a critical safeguard. It ensures:
✅ Both parties fully understand the nature and consequences of the agreement and the rights they may be giving up.
✅ The agreement was entered into voluntarily, without pressure or duress.
✅ It is much harder for either party to claim unfairness or a lack of understanding years down the line.
Skipping ILA might save money now, but it significantly increases the risk that a court will set aside the entire agreement during a divorce, leading to much greater legal fees and uncertainty later.
Ready to Protect Your Future?
These 15 questions are just the starting point. Now it’s time to create a Marriage Contract that actually protects you.
Don’t Leave Your Financial Security to Chance
❌ DIY templates get thrown out in court
❌ Paralegals lack the specialized expertise
❌ Junior lawyers may miss critical clauses
✅ Certified Specialist in Family Law ensures your agreement is enforceable
Get Your Expert-Drafted Marriage Contract
Investment: $2,500 + HST
What’s Included:
✓ Customized Marriage Contract prepared by a Certified Specialist in Family Law
✓ Personal consultation with Steve Benmor to discuss your specific situation
✓ Expert guidance on protecting your assets, business interests, and family wealth
✓ Legally enforceable agreement designed to withstand future challenges
✓ Peace of mind knowing your prenup is backed by over 30 years of experience
The Process:
Step 1: Purchase Your Agreement
Secure your expert-drafted Marriage Contract online. Your investment includes everything listed above.
Step 2: Complete Your Questionnaire
Fill out a simple questionnaire about your financial situation, relationship circumstances, and specific concerns.
Step 3: Schedule Your Consultation
Book your personal telephone or in-person consultation with Steve Benmor at a time that works for you.
Step 4: Review and Sign Your Agreement
Receive your professionally drafted Marriage Contract, review it with Steve, and complete the signing process. Both partners should receive independent legal advice to maximize the agreement’s enforceability.
For Second Marriages: Protect What You’ve Built
You’ve been through this before. You know what’s at stake. Whether you have children from your first marriage, significant assets you’ve accumulated over decades, or retirement savings you can’t afford to split again—you understand that clarity now prevents conflict later.
A Marriage Contract ensures:
✓ Assets you brought into the marriage stay protected
✓ Children’s inheritance (if applicable) is clearly defined
✓ Your retirement and estate plans remain intact
✓ Both families understand and respect the boundaries
✓ You start your second chapter with confidence, not uncertainty
Protecting your future isn’t about distrust—it’s about wisdom gained from experience.
For Business Owners: Keep Your Enterprise Secure
You didn’t build your business to risk losing it in divorce. Whether it’s a professional practice, family business, or company you’ve grown from nothing, your enterprise is your livelihood—and potentially your employees’ livelihoods too.
A Marriage Contract ensures:
✓ Your business value at marriage is protected
✓ Growth during marriage is addressed fairly
✓ You avoid forced sale or liquidation
✓ Your business remains viable no matter what happens personally
Entrepreneurs who’ve worked hard to build their business deserve to protect it.
Why Choose Steve Benmor?
✓ Certified Specialist in Family Law (one of Toronto’s 24)
✓ Fellow of the International Academy of Family Lawyers (one of only 56 in Canada)
✓ Master of Laws (LL.M.) in Family Law
✓ Over 30 years of experience in family law
✓ Regularly interviewed as a family law expert on television, radio, and in newspapers
Steve Benmor understands that the most important things in life are family, children, and having healthy relationships. His mission is to help couples stay out of court, keep costs down, and protect their futures with clarity and confidence.
Ready to Get Started?
Purchase Your Marriage Contract Now →
Questions before purchasing? 416-489-8890 | steve@benmor.com
Benmor Family Law Group
77 Bloor Street West, Suite 600, Toronto, ON M5S 1M2
This checklist is for informational purposes only and does not constitute legal advice. Every situation is unique, and you should seek advice specific to your circumstances. To discuss your specific situation with Steve Benmor, Certified Specialist in Family Law, contact us at 416-489-8890 or purchase your agreement at benmor.com/prenups-cohab-agreements.