Love and Money: The Three Conversations That Change Everything

 In over twenty years of working with enterprising families, I often help them navigate issues that arise when love and money become intertwined. Consider the following real-life scenarios (identifying info changed):

A Next Gen family member who is away at university finds himself picking up the tab for his friends, feeling guilty about having more money than they do. But in time his friends begin taking advantage and expect him to pay for everything.

A newly engaged couple finds themselves in gridlock when attempting to negotiate their prenup. She resents feeling like he is being greedy and fears that this relationship may be about her money. He is deeply offended that she doesn’t trust him and that she is already planning for divorce.

A wife of a successful entrepreneur is devastated when her best friend, whom she’d hired to do some work for her, changed the terms of their agreement and refused to release the commission until the wife paid her 6x what they had agreed to. Lawyers got involved. They no longer speak. 

Each of these scenarios highlights the conflation of love and money that so often happens when there is wealth involved. With the best of intentions, and with generous hearts, relationships can become transactional and the foundation of love can become fractured by deep roots of insecurity, regret, resentment and guilt.

Rather than go into detail with unlimited scenarios, there are a few approaches that can assist in any situation that further relationships while managing expectations (and presumptions).

Approaches to Trust when Money is Involved

1. Maintain Awareness – of your personal motivations. When the underlying motivation is guilt, generosity tends to lead to entitlement, manipulation and dissatisfying relationships on both sides. When you are clear about the purpose of your wealth and the core values that you want to further with your resources, decisions are made in alignment with your values and it’s easier to say no with clarity and care.  
2. Pay Attention - to the motivations of others. This is not about being wary or distrustful. It’s about being present and awake to reality versus the story you may have in your head. Honor the little things that don’t feel right and catch them quickly. Your body will tell you – a sinking feeling in your stomach, a tightness in your throat, a contraction around your heart. These signals tell you that you need more data and to not blindly trust. People show their values and motivations with how they use their money (and the money of others). When you ignore what your gut tells you, there will likely be disappointment or worse, in the future.
3. Assess trustworthiness – do they show up truly caring about what you care about? Are they sincere and demonstrate that they mean what they say? Are they reliable and do what they promise to do? And, are they competent in managing hearts as well as money? For example, notice, if they ask for a loan (or you offer to give them one), do they pay you back or always have excuses or avoid discussion about it? Best to start with a small loan and clear agreement about repayment, interest, and timeframe. Then it’s easy to observe how they fulfill their side of the agreement. 

I received an inheritance when my stepmother died. At that time a friend was going to lose a family home due to relatives wanting to sell. She needed it for her special needs adult son and did not have enough cash on hand to buy out her relatives. I offered to loan her the money – knowing it was in keeping with my stepmother’s values of helping those you love when they are in need – and we drew up a clear loan agreement with a stated fixed interest rate and time frame. She set up automatic payments and sent a thank you note with each installment. And I thanked her for showing up so consistently. Our friendship continues to thrive.

4. Address concerns – don’t wait! At the first sign of something not feeling right, use it as an opportunity to get to know the other person better and to determine what their intentions and motivations are. If someone is less than excited about a generous gift, what was missed? What could have been done differently? If someone shows up expecting more than you’d like to give, what boundaries and expectations do you see need to be expressed and explored.

People often avoid discussing concerns out of fear of harming the relationship or hurting the other person’s feelings. They don’t want to appear stingy or punitive, as they enjoy being generous, but just don’t want to be taken advantage of. While each gift or loan or request in and of itself may be insignificant in the face of financial disparity, it’s how the gifts add up over time and the resulting expectations and presumptions underneath that matter. 

Addressing concerns early is an act of care for the relationship itself. And there are ways to do this that build trust and that honor both the relationship and your own clarity about what feels right.

How to Have Money Conversations:

Here are a few healthy ways to have a conversation about concerns related to love and money:

1. Lead with care – first and foremost, share what you love about the other person, what you enjoy most about your relationship, and how much they mean to you. Ask them what they care about the most in terms of their relationship with you as well. Give them time to answer and take it in, receiving what they say with a heartfelt “thank you”, or “that means a lot”. Notice how you feel about what they are saying – does it seem sincere? Do you have an odd feeling about it? (that’s the paying attention discussed earlier).
2. Share the concern and be specific, providing a recent example. You could start with something like: “For the sake of furthering trust in our relationship, I’d like to revisit how we are relating together with money….” 

For the college student, it might continue with: “…Last night I was really uncomfortable with how you presumed I would pay for everything, and when you ordered another round for everyone without checking with me first, I felt disrespected. I realize I’ve set up that expectation and want to see how we can shift that.” If they respond defensively and make you wrong, or if you find yourself apologizing or feeling even worse, chances are this relationship may be out of balance. If they apologize and empathize and express gratitude for your generosity, you have a true friend. This conversation can bring clarity, but when you don’t speak up, you are always left wondering.

3. Complete with appreciation. Conversations like these aren’t easy, but they are what allow us to have authentic, vulnerable, intimate relationships – something that makes us uniquely human. They feel risky and uncomfortable, but the risk is worth it. Taking time at the close of the conversation to appreciate one another for the willingness to share what’s in our hearts serves to actively and intentionally strengthen the relationship. Researchers* have shown that couples who move through conflict with care and with repair are much more likely to stay together. It takes courage to step into potential conflict and stick it out to a fruitful end. By continually focusing on a positive, shared future together, you co-create a strong foundation that can withstand the inevitable challenges your relationship will face.

Conclusion

Love and money will always intersect in our lives—the question is whether that intersection strengthens our relationships or erodes them. When we approach these conversations with awareness, presence, and courage, we create the conditions for authentic connection. The discomfort of addressing concerns early is temporary; the cost of avoiding them compounds over time in the form of resentment, broken trust, and lost relationships.

The families and individuals I've worked with who navigate love and money most successfully share one quality: they refuse to let unspoken expectations fester. They choose the temporary vulnerability of difficult conversations over the permanent damage of silent disappointment. In doing so, they don't just preserve their relationships—they deepen them.

*from Fight Right: How Successful Couples Turn Conflict Into Connection by Julie Schwartz Gottman and John Gottman