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Dating & Money: 7 Questions to Ask (and What Not to Ask)

by Ahmed Hassan - World News Editor

Dating in the 21st century presents a unique set of challenges, and navigating the topic of finances is often among the most daunting. While direct questions about income or net worth can quickly derail a promising connection, understanding a potential partner’s financial mindset is crucial for long-term compatibility. Experts suggest shifting the focus from specific numbers to broader conversations about values, habits, and expectations surrounding money.

The Awkwardness of Money Talk

A survey by Country Financial revealed that 26 percent of respondents found it difficult to transition from managing finances as individuals to doing so as a couple. This discomfort is understandable, as money is rarely a romantic topic. Many couples, like one pair who recounted their experience to CNBC, avoid the conversation altogether until a significant event forces the issue – such as receiving a student loan bill unexpectedly. This reactive approach, however, can lead to conflict and misunderstandings down the line.

The reality is that financial decisions, both large and small, are a daily occurrence in any committed relationship. From choosing between regular and premium gasoline to deciding whether to cook at home or dine out, these choices reflect underlying philosophies and feelings about money. These feelings, often deeply ingrained, can become significant sources of contention if not addressed proactively.

What Not to Ask – and Why

Directly asking “How much do you make?” or inquiring about someone’s net worth on a first or second date is likely to be met with discomfort, and potentially, a swift exit. The irony, according to financial experts, is that these questions don’t necessarily reveal what you’re trying to learn. A high income doesn’t guarantee financial stability, while a lower income doesn’t preclude responsible financial habits. The goal is to understand how someone thinks about money, not simply how much they have.

Seven Questions to Reveal Financial Mindset

Instead of focusing on concrete figures, consider these questions designed to elicit more revealing responses about a potential partner’s financial approach:

  1. “Where did you grow up and what was it like?” This seemingly innocuous question can provide insights into the environment someone was raised in, their family’s norms, and their perception of a “normal” lifestyle.
  2. “Tell me about your family. What were they like when you were a kid?” Exploring family dynamics can reveal formative experiences and the values that shaped a person’s relationship with money – stability, ambition, generosity, or perhaps a sense of scarcity.
  3. “What was your first job?” This question offers a window into someone’s work ethic, motivation, and sense of independence. Their experience – whether positive or negative – can reveal how they view earning and financial security. Did they save their earnings, spend them immediately, or contribute to their family?
  4. “Are you more of a planner or a wing-it person?” This reveals how someone handles uncertainty, a common element in financial life. Understanding whether someone prefers meticulous planning or spontaneous action can help gauge compatibility in financial decision-making.
  5. “What’s something you’ll happily spend on and something you refuse to overpay for?” This question uncovers personal values, and priorities. Responses can reveal how someone perceives convenience, health, quality, experiences, and savings.
  6. “What’s your ideal vacation?” Vacation preferences often reflect financial expectations. A preference for camping versus luxury resorts can indicate differing approaches to cost and budgeting.
  7. “When you get stressed, what do you like to do?” Stress significantly impacts spending and saving habits. Understanding how someone copes with stress – whether through planning, distraction, or spending – can provide valuable insights into their financial behavior.

Moving Towards Direct Conversations

As a relationship progresses and shared financial decisions become necessary – such as moving in together or sharing expenses – more direct conversations are inevitable. However, experts suggest delaying these discussions until a strong foundation of trust and understanding has been established.

The key is to avoid treating money as a separate entity, but rather as an integral part of building a shared life. By starting with open-ended questions that reveal a partner’s values and habits, couples can navigate the often-awkward topic of finances with greater ease and build a stronger, more sustainable future together. As Douglas A. Boneparth, a wealth management firm founder, and his wife suggest in their book, “Money Together,” fairness and teamwork are essential components of a successful financial partnership.

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