(844) 845-4219 » Women’s Biggest Regret? It’s a Tie between Romance and Money

Women’s Biggest Regret? It’s a Tie between Romance and Money



This is a statistical surprise: In one study, 44 percent of women said they regret at least one romance in their lives. That’s the same exact number in another study about women who regret their lack of investment skills.

So why are so many of us equally terrible at love and money? I have a theory, and it explains both problems.

First, let’s define those problems

Northwest University (near my hometown of Chicago) once asked men and women about their romantic regrets. Not surprisingly, the study found more than twice as many women had those regrets as men did – 44 percent to 19 percent.

Let’s be honest, both society – and women themselves – beat themselves up over failed relationships. We blame ourselves, even when the men aren’t working nearly as hard at the relationship as we are. We wonder where we failed.

Men find it much easier to forgive (themselves) and forget (the breakups). They don’t dwell on their losses – in love or money.

Study after study shows men are willing to take more investing risks than women do. That has a lot to do with confidence. Women aren’t confident enough even when they should be. Men are overconfident about damn near everything – from their looks to their brains.

Only 9 percent of women think they make better investors than men, despite research showing that they earn consistently better returns,” says the Motley Fool after analyzing two decades of research on this topic.

No less than the Harvard Business Review has a theory why this is…

The most common one holds that in primitive societies men were forced to fight to gain status and to compete for positions of power. Women, on the other hand, were more likely to be caregivers.

Of course, that Harvard research was conducted by two men and only one woman!

My theory is a little different: Women “invest” in our relationships. We “invest” in our men. And what happens? A lot of times, those investments fail, no matter how much of ourselves we pour into them.

God knows I tried myself. I’ve been divorced, and afterward, I was exhausted. Divorce is always stressful, but I was already worn out from trying to salvage the marriage – even before I had to spend a lot of time and money ending it.

I don’t know any woman who hasn’t lost out on at least one “investment” in a guy. So, it only makes sense that women would say to themselves, “If I can’t grow a relationship with someone I’m literally sleeping next to, how am I going to grow an investment in stocks I know little about?”

We need to break that mindset. But it won’t be easy. So, let’s start small.

Second, let’s fix one problem

Of course, another theory about this involves women’s wages and debts. I don’t care what anyone says, women still earn less than men for many of the same jobs in this country. And women have more debt because they have more responsibilities.

For instance…

Women hold 58 percent of all student loan debt. Female student borrowers have an average debt is 9.6 percent higher than their male peers one year after graduation. Women take an additional two years on average to pay off student loans.

Here’s what I’m suggesting: Treat your debts like you treat your dates.

Think back to your last failed relationship. What was something you did to make yourself feel better? You didn’t just jump into another serious relationship. You casually dated to figure out yourself and what you want in a partner.

In many ways, casual dating is less stressful than a relationship because our expectations are lower. We’re just out to have fun and learn a few things about ourselves and other people. We need to think about investing the same way.

So, here’s what you do, in three easy steps…

  1. Call or visit for a free debt analysis.
  2. When you get help to eliminate your debts, keep track of what you save.
  3. Invest that money in the stock market, or in riskier parts of your retirement accounts.

It might look like this: You have $10,000 on your credit cards, and your interest rate is 20 percent. That means you’re paying $3 for every $15 you charge. As you start to gradually pay off your debt, you funnel savings into, say, the growth fund in your 401(k).

Over time, you’ll notice riskier investments will soar and plummet. Your heart rate will soar, and your stomach will drop. But then you’ll notice something: In a few years, you’ve made a lot of money. Those ups and downs rarely stay down for long, and they stay up long enough to make a difference.

As someone who’s become an expert on making money and struggling with men, I promise you this: At the end of the day, you’ll find that dealing with money is much easier!

The views and opinions expressed in this article are those of the author(s) and do not necessarily reflect the opinions and/or policies of

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