We planned to spend Diego’s 38th birthday in San Pancho, a small beach town 50 kilometers north of Puerto Vallarta. While en route with our two pups and Yerba mate, I had the idea to go through the 36 Questions That Lead To Love exercise that had gone viral, supposedly helping couples fall deeper in love. For the next hour, we asked each other questions such as, “If you could change anything about the way you were raised, what would it be?” and “If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?” It’s amazing how much we can learn about our partners even after four years into the relationship. We arrived in San Pancho at an outdoor cafe where we ordered a burger and fries and continued the quiz. Shortly after dinner, we wandered down to the beach, barely making it before sunset. With the last glimpse of the sun, Diego turned to me and started telling me how wonderful our relationship was and how much he admired me. Of course, I loved every second of it, even though his eloquent verbal expression and emotional vulnerability caught me off guard. These aren’t qualities that typically come naturally to him, or to many men for that matter. I quickly realized what was happening, and sure enough, he pulled out a beautiful engagement ring, asking me to make him the happiest man on earth.
There was a slight shift in our relationship after the engagement. There was excitement and a heightened sense of love for Diego. There was also a seriousness that came with knowing you are committing your life to one person, and a sense of motivation to align in our values and decisions that will eventually face us in our marriage. First and foremost, Diego and I come from culturally-opposite countries. For example, in Canada, it is normal for your family to stay one week (two weeks maximum) in your home when visiting. My parents always told me “not to overstay my welcome” when staying with friends. In Argentina, an open-door policy is the norm. This means friends and family are welcome to stay with you for months at a time. Later that year, this became clear when I arrived home from Medellin and found Diego’s best friend and his girlfriend in one spare room, his mom in the other spare room, and his other friend and his dog camping on the patio. Oh, and the news that his mom would be staying with us for four months.
I love the fact that Diego (and the Argentinian culture) embraced community and togetherness. I really do. I almost envy it. I remember observing them all in our living room, seeming so free, relaxed, and happy in their time together. On the other hand, I felt constrained and not free to roam and “just be” in my home. I felt guarded and craved my own space. But then I remembered the idea that relationships serve as a vehicle for growth, and I knew this was an opportunity, no matter how uncomfortable it felt. So, I embraced his friends and family, enjoying the closeness it brought… until one day, his mom casually mentioned wanting to extend her trip by another month or two.
In every healthy relationship, there exists mutual understanding and compromise. In this instance, I felt the need for Diego to also understand where I come from and what’s considered a cultural norm in my country. So, as one of our first important conversations as an engaged couple, we tackled: setting boundaries with family members. We decided that family and friends could come to stay with us but for no longer than a month, at which point they would need to get their own place.
After navigating cultural differences and setting boundaries, a new topic surfaced that would test our unity and understanding as a couple: money. In many relationships, money isn’t just about numbers and accounts—it’s tied deeply to values, dreams, fears, and the life we envision together. For Diego and me, it would become a central theme of discussion, revealing not just our spending habits, but the underlying values and priorities we held.
Let me provide some context before diving into our deep, intimate conversations. As the co-founder and CMO of a matchmaking company, I spent years writing on the topic of love, dating, and more recently, how money is inextricably interwoven into our relationships. I had just read I Will Teach You To Be Rich by Rami Sethi and recorded an entire podcast season on dating and money. As a child of parents who divorced due to money issues, I knew I didn’t want to become a statistic. So, I made it a priority to become financially aligned with Diego.
As a first step, Diego and I read Secrets of the Millionaire Mind by T. Harv Eker and had weekly discussions after each chapter. This was enlightening for many reasons, my favorite being that I gained insight into his childhood and where he adopted his money mindset (and vice versa). Some of the questions we explored from the book were:
- How did your parents talk about money? How did they manage it?
- How are you identical or opposite to either of your parent’s money habits and ways of being?
- How has this affected your financial life?
We both recognized that growing up, our families avoided discussing money. As a result, like many of our friends, we lacked education on how to converse about or manage finances, especially given their significant impact on our lives and relationships. Interestingly, we discovered that our economic backgrounds were quite similar—middle class with numerous financial challenges—which inclined us both toward saving rather than spending. However, I tended to be more future-oriented, while Diego leaned toward the present, occasionally making planning challenging. This difference, however, taught me the importance of being in the present moment.
We then each wrote a vision statement of what we envisioned our lives to be in 10 years and then reconvened to share them. We addressed lifestyle expectations, where we want to live, considerations about having kids, our life values, and why we want to grow our money. Writing them separately allowed for individual reflection, ensuring we didn’t merely conform to what the other might say. After completing this exercise, it became evident that Diego and I both prioritize freedom, travel, and have a shared aspiration to build a company together. Seeing our values line up like this solidified our direction together.
Once we addressed the underlying, subconscious reasons shaping our attitudes and actions towards money, we then turned our focus to the numbers. We began by tracking our finances followed by a review of our spending habits. Some of the questions we used included:
- How much money do you make?
- How much money have you saved?
- How much debt do you have?
- What are your monthly expenses/spending?
- What are your long and short-term financial goals?
- What are our joint financial goals?
After months of intimate conversations, I felt that we were finally reaching our target of mutual understanding and the ability to create inspiring financial goals together. Having a common goal with your partner keeps you both working as a team, not against one another. Furthermore, having a joint goal can be a huge motivator if that goal lights you up and gets you excited for your future. Imagine having a joint goal to buy a second home in Italy so you can spend your summers there. Just the thought of being able to paint by the sea while sipping Chianti might be enough to get you both working on the same team.
You may be wondering, what is our joint financial goal? Well, we loved the idea of reaching 1M in investments so we decided to each open an investment account in which we’re aiming to invest 80% of our income. I know this seems like a massive percentage. However, we don’t have debt, a mortgage, car payments, or kids, and we currently live in Mexico where our expenses are a fraction of what they would be in the US, so this is very realistic for us. We want to reach “financial independence” in our 40s and now we have a game plan for how to do it. “Financial independence” is when your investments pay for your life in perpetuity so you never have to work again if you don’t want to. We both realized that saving your way to financial independence is not feasible and that while the stock market as a concept looks and feels risky, it’s actually a safer—and smarter—saving strategy.
You could say our engagement was lengthy, elaborate, and intense (in the best possible way). It pushed us to have serious conversations that will influence the rest of our lives, and it paved the way for a more stable marriage. Of course, life will throw wrenches at us and we’ll have to shift and adapt— or maybe Diego and I will evolve into different people from who we are now— and again, we’ll have to shift and adapt. But I feel like we mastered some of the most important keys to a relationship: the ability to listen, reach mutual understanding, and stay curious about one another.