Prior to your first date with an independently wealthy man, you should feel confident that you are not wasting time or energy meeting with a (potential) pretender. The addage “I shaved my legs for this?” comes to mind.

Here is some advice from a man who grew-up with money and continues to make money today.

Filtering out the pretenders from the contenders can be a bit tricky. Plus, you don’t want to offend anyone right off the bat by asking for a copy of financial statements. So does a woman screen candidates even before the first date?

There are a number of questions that you can raise during an intital conversation that sound casual and non-threatening, but can do a lot to open a man’s true character.

Remember, the presentation is as important as the sunstance here. There are a number of casual questions that a man should be happy (if not proud) to answer, which will tell allow you to ease into the substantive questions that will usually expose the pretenders.

The good lead-in questions should allow a man to “talk about himself” in a positive way. For example, asking simple questions like “where did you go to college?” “were you in a fraternity?” “did you play sports or on the chess team?” will allow the guy to start thinking about his youthful “glory days” which he should be happy to discuss. If he came from money, I can promise you he went to a good college, was in a fraternity, and had to involved in either a sports activity or a nerdy activity like chess club. By addressing these questions, you can determine if the guy “grew up” with money. These are the best guys to land because people who grew up with money always believe the money will be there. They don’t know any other way of life. And since they believe the money will always be there, that should be an indication that they are secure in what they are doing.

However, there are plenty of men who have “new money” and had to earn their wealth from nothing. These men may not have gone to college or probably could not afford to be in a fraternity. But even this group was either active in sports or, once again, played on the chess team. Get them to talk about that.

Eventually you want to ask them questions like “to what do attribute your success?” or “which is better have, a hard work ethic or good luck?” Regardless of how they answer you might kick in the comment “is it true that the harder you work the luckier you get?” to lighten the conversation.

After you have laid a groundwork such as what I have outlined above, the next questions will say a lot about the person. The key topics are investments and charities. That is what you are leading up to in a soft casual way.

All men of substance have their “ideas” about what a good investment is and have their favorite charities. So lead into a question like “so where is a successful man like you investing your money these days?” He should answer with stocks, bonds, real estate or gold. It really does not matter which one he picks so long as he identifies an investment that he likes. Now is the time to listen carefully. Let there be a long pregnant pause after he answers. If he says “I am hedging with equities and bonds” or anything really, that’s a good start but say nothing in response. Make him fill the void with more information. If he is a pretender, he will get nervous and say that he is not actively investing or that he has all of his money in cash or that he let’s someone else do it for him. Bologna. That’s a bad sign. But if he fills the void but providing a lot of boring detail that he is looking into an investment into real estate investment trusts, blah, blah, blah, that’s great. That’s a sign that the man is a contender, and understands (or believes he understands) money. A pretender won’t know what to say and will stumble or skillfully change the topic. You can end this line of questions by asking if he thinks Apple is a good investment. He’ll say yes or no, but regardless, you can feel that you have an idea whether or not he actually has money by how he views his current investments.

The final line of questions have to do with charitable investments. All wealthy men will have a pet charity that they will contribute to. It could be his Church. It could be his Alumni Association. It could be Save the Dolphins. Again, it doesn’t matter where he makes contributions. What matters is that he is making charitable donations. If he isn’t, that’s a very bad sign.

Once again, your lead into this arena should be careful. You might say that you are a very giving person and ware thinking about making a small charitable contribution “to give something back” to society and ask if he has any recommendations on where you should donate. Aha!! You express that you are kind and giving person and now you get to find out a key piece of insight about him. He should say directly that he is donating to his Church or to a specific entity. If he cracks a joke like “I believe charity begins at home — my home” then that’s a red flag for you right there. But if he says, “This year I’ve decided to help out the SPCA” or whatever — that’s a great sign. If he says “I’m still thinking about it” ask him where he has donated in the past. Don’t let him off the hook here. Emphasize that you really want to “give back” to society a little of your blessings and seek his advice — if he can’t give you any this is a very bad sign.

So there you go — that’s my first date screening advice that will, I hope, help you beautiful ladies sort out the pretenders from the contenders.

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