Falling in Love Again—With Eyes Wide Open

by Kevin Rigg, CFP®, CPA®


Finding love later in life is often an exciting and meaningful experience. Perhaps my heart is still lingering in Valentine’s Day mode, even though this article is arriving in March. But while romance may come easily, it can also introduce complexities that require thoughtful and intentional planning. With the right preparation, couples can establish clear expectations and priorities early in the relationship—allowing them to focus on what matters most: building a life together.

A helpful starting point is to step back and reflect on personal history and values before establishing goals for your shared future. Consider beginning with questions like these:

  1. Are there financial commitments we have already made to our loved ones?

  2. Are there assets we intend to share and others we prefer to keep separate?

  3. What does financial security mean to each of us at this stage of life?

  4. How do we want to care for one another if one of us is no longer here?

  5. What would provide us with the greatest peace of mind moving forward?

Answering these questions can help lay the groundwork for building a thoughtful plan together. Documenting those decisions is also important. One common way to do that is through a prenuptial agreement, often called a “prenup.”

Documenting What Matters Most

Prenups are sometimes viewed negatively, as though they are purely defensive tools meant to protect one party from the other. While they can certainly serve that purpose, when approached transparently and constructively, they can instead provide clarity, build trust, and align expectations within the relationship.

While a prenup can outline intentions, a well-designed estate plan helps ensure those intentions are carried forward. Reviewing your estate plan is recommended during any major life transition, but it is especially important when entering a later-in-life marriage. Working with your attorney, you may want to review your estate plan to address at least the following:

  1. Wills and trusts reflect an asset distribution plan consistent with your goals.

  2. Beneficiary designations align with your overall estate plan.

  3. The individuals named for key decision-making roles reflect your current wishes.

Engaging in thoughtful planning like this requires effort, but when done well, it helps clarify priorities, provide needed support, and avoid unintended burdens on those you leave behind. Most importantly, it allows you to honor what already exists while protecting what matters most as you build a new life together.