I appreciate how difficult it can be to move forward, especially when you question the intentions of the people you meet. I find it interesting that you say your husband left you in control of the estate. Hmm. You should have felt in control while he was here with you; his death should not have triggered your sense of control—legal or emotional.

That has me thinking that the issue isn’t your relationships with men, but your relationship with money. And it is important to understand that money itself is never the problem; what trips us up is how we feel about the money we have (or don’t have). I can tell you this is the same whether I am talking to someone panicked over an $8,000 unpaid credit card bill or someone handling an eight-figure estate. If there is a money concern, it is because the person lets money control the situation. Money has no power on its own—it only has power that we choose to give it.

My sense is that, right now, you let your money define you, and that, in turn, attracts the wrong type of man. Slow down and think about that. What do you believe in? What do you love? What do you hate? When you can answer those questions without mentioning your money, you will have everything you need, because you will understand that who you are has nothing to do with what you have. When your actions exude that attitude, you will find the right type of man. And who knows, perhaps he has 10 figures that his late wife left him.
Suze Orman, author, Women & Money and host of CNBC’s The Suze Orman Show

It is prudent to make sure you’ve taken some legal steps to keep your money from presenting obstacles in any future relationships. The best way to do that is to keep all things pertaining to it seemingly out of your control and totally private to the extent possible. You don’t say whether you have children and whether you have any charitable intentions, so it is hard to go too far with advice. But at the very least I would suggest:

• Create a revocable trust and fund it with the assets in your estate.

• Tell any suitor that your separate funds are just that, and that they are in a trust, invested independently by managers selected by your attorneys.

• Clarify that your attorneys and investment managers have instructed you to keep your affairs private and not to discuss them with anyone.

• Explain that your attorneys insist that a prenuptial agreement (which keeps your assets separate for all time) is a condition precedent of marriage.

• Make it clear that this is the end of the discussion, as you are not very informed beyond the above, nor do you care to be. It is important that you present yourself as having little interest in money. The less said, the better.
John F. Schaefer, The Law Firm of John F. Schaefer, Birmingham, Mich.

When it comes to dating and finances, things are never easy. Keep in mind that men naturally want to provide and contribute. If it appears that you don’t need anything (or anyone), your date may feel that there is no place for him in your life. Don’t bring out your bank statements too quickly and never lead with information about your finances. You may also want to limit the amount of diamonds and jewelry you wear. That will help potential suitors focus on you—and not your money.

Looking for men within your financial bracket may provide comfort, but it might limit your options. Try to remain open-minded about what his financial picture should look like. Men who are in solid, responsible shape financially and who meet your other criteria may be a great match for you. If the subject of finances comes up, say that you are fortunate to have yours in order and leave it at that.

In the end, dating is about accepting who you are and what you have to offer. This attitude will intimidate some and fascinate others. These are just feelings, and the more comfortable and autonomous you remain, the more you will tolerate people’s reactions. But first, you must be secure with yourself and comfortable with your money. Once this happens, other people’s reactions will have little impact.
Lisa Clampitt, founder of VIP Life, New York