How Rich Guys Screw Up Their Chances with Women

Everyone else assumes that the successful dudes get all the babes, but it turns out that's not always the case. So I had to look into what was going on here.
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I have several super-successful, single male friends here in Los Angeles who also happen to be smart, kind, educated, and decent-looking. They're solid guys through and through. And it just kills me that they can be so successful in every other department in life but romance.

Everyone else assumes that the successful dudes get all the babes, but it turns out that's not always the case. So I had to look into what was going on here.

One of them, Aaron, who is in his mid-40s, recently invited a very attractive 24-year old woman to dinner. She asked to be taken to one of the most expensive restaurants in town, and Aaron obliged.

He'll never forget what happened at the restaurant: she proceeded to order everything on the menu. Then when they brought her the dishes, she sent them back. Not once. Not twice. Not three times, but FIVE times.

The entire staff of the restaurant was fed up with her, as was Aaron. So he paid the bill and excused himself even before the meal was fully over.

That vignette illustrates a bunch of the mistakes rich guys make. Aaron lost two hours, some pride and a couple of hundred bucks, but sadly, many other men (and not just wealthy ones) waste far more time, money and effort as a result of the following:

1) They try to buy themselves into a woman's favor.

Many rich guys have a terrible habit of spending lots of money on a woman they don't know very well. Super-fancy dinners (like Aaron's above), a bracelet engraved with her name, cross-country chartered flights -- these are just some of the things I've seen and heard men do for women on a first date. The idea is "I've done this for you -- please like me."

You need to stop that, buddy. Like, now.

Aside from the fact that this sort of behavior can make a man's motivations suspect -- triggering the "I wonder what he really wants from me" alarm in a woman's head -- there are fundamental reasons why this is a bad idea.

The first is neurological. In animal behavior, a reinforcer is a reward which tends to increase the frequency of a behavior. Timing is key: the molecular mechanism dictates that a reinforcer works only if given shortly after the desired behavior.

If you give the reward before the behavior, it's not a reinforcer -- it's just a bribe. You're reinforcing nothing. So in the future, you're likely to get even more of -- nothing. You have zero leverage because you have given your power away. Moreover, a bribe usually doesn't increase the respect of the bribed for the briber.

Generally, people will like you not because of what you have but because of how you make them feel. So instead of spending lots of money early on, be compelling. Three of the five methods of being compelling from the Tao of Dating for Men are focusing your attention on her, being fun and being somewhat mysterious.

The second reason is more spiritual. If you're looking for a meaningful connection with a woman, throwing money around can distract from that.

Beyond your achievements and possessions reside your heart and soul. After the honeymoon period, that's what's going to matter, and that's the level at which you'll want to be connected with a woman.

Ideally, you want that to be the foundation of your relationship. Moreover, if you succeed in enticing a woman into your life with material displays, you'll make it far more difficult to discern whether she's into you or just your baubles.

That said, wealth is as attractive to a woman as a shapely body and pretty face are to a man, so by all means, use that to your advantage. Just remember the writer's old adage: show, don't tell.

Tip well, throw nice parties at your palatial pad, be involved in charitable causes. That's showing -- magnanimity is quite appealing. But don't necessarily bestow gifts upon people before they've earned them. That's telling, and it's just a fancy way of seeking approval. It diminishes your power.

This brings us to the second point.

2) They abdicate their leadership role as a man.

He gets stuff done. He's a leader of men. He kicks major ass in almost every department in life. He is one successful dude.

Yet, somehow, when it comes to his interactions with women (especially the young pretty ones), he relinquishes all that power. He starts to chase and seek approval. He lets her call the shots. He thinks that if he gives her what she wants -- like Aaron did when he let his date choose the restaurant -- she'll like him better.

No, no and no.

Since time immemorial, women have been attracted to men who are older and of higher status than themselves. The sophomores want to date the seniors. Not to say that you're ancient, but you're the senior now, brother.

Congratulations -- as the older man, you've earned the right to be chased. Now what are you doing pretending that you're the one chasing her? Why are you trying to impress her?

Stop that already. Behold the yin-yang symbol, or taijitu:


Notice how there's a little dot of black (yin, or feminine energy) in the field of white (yang, or masculine energy).

For men, you can think of the yang as the main dish, and the yin as the spice. The spice enhances the flavor of the dish.

Chasing her is yang. Leaning back a little and letting her chase you is yin.

So all ye powerful men out there: bring on some of that yin. Lean back. Evaluate her instead of trying to prove yourself. Assume the stance of the picky selector. What qualities makes her appealing? What makes her a good companion?

Instead of trying to qualify yourself to someone who is probably younger, less experienced and less powerful than you, allow her to qualify herself. Be the interviewer, not the interviewee.

In four words, don't be a wimp. Stay the leader instead. Ladies love cool leaders.

3) They try to parlay friendly concern into romance.

Jeff is another friend of mine in town who's very successful in the entertainment field. And often when he meets a beautiful, young actress, he offers to help advance her career with his vast network of influential contacts.

This is a lot like the 'buying her favor' ploy up in item #1, except that it's less sincere. At least the guy who buys a woman flowers or asks her to dinner is straightforward about his interest in her.

If you're a networking god and just love to connect people together, by all means keep that up. At the same time, if you're interested in a woman, quit being a wimp (current euphemism: 'nice guy') and own up that you're interested in her as a woman. You Tarzan, she Jane.

Once you're in the friend zone with a woman, the chances of you getting romantically involved with her diminish dramatically. That's why being a little aggressive and making your intentions clear at the outset can increase your chances of success. If she says yes, game on. If no, then you've just stopped wasting your time. You win either way - very Tao for you.

The power is within you,
Dr Alex
Twitter: @dralexbenzer

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