I’m Inlove With A Boss Lady – Help Me!

“So, I met this girl. I really like her, but I just found out she’s my boss’s boss. Do I go ahead or do I quit while I’m at it? I mean, the girl I like earns more than I do”. I think I’m inlove with a boss lady!

Lol. This scenario is most typical for the womenfolk. You know. Girl meets boy, finds out he is super-rich and all the doubts and insecurities start to pile up. They manage to sort things out, or they don’t. This doesn’t happen to guys often unless he’s a professional gigolo. Like, how do you explain to yourself that the woman you really like could probably pay you for being her man and not worry about going broke? And how do you buy her gifts without feeling like she could buy them for herself without a second thought?

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Guys are hardwired to be providers. It’s an instinct that is never going to die out. A guy wants to be able to show off his babe and spoil her silly and probably impress the heck out of her friends. All of that is going to be next to impossible, when she is wealthy in her own right and your net worth is not half of hers, or close to half. You’re not poor, no, but compared to her and the people you see her with, you feel like you are. And your heart is refusing to see things realistically.

Most guys do their damnedest to forget this girl. Some try to do more, to feel worthy of her. The “demons” jump in, get what they want, and leave behind a broken heart. But what do you do when everything within you is screaming that she is the one and there are signs that she may like you too?

First, answer these questions.

What Are Your Personality Traits?

Yep. These traits will determine everything that happens between the two of you. Do you get jealous easily? Do you have a quick temper? Are you laid back or actively engaging? Are you a dominant male, the take-charge kind of guy? What are your thoughts about women? Do you prefer your woman barefoot and pregnant or wearing heels and a business suit?

If you’re able to answer these questions and a lot more that will prop up as you honestly examine yourself, you will be able to pinpoint with near accuracy what a relationship between the both of you will look like.

What Are Her Personality Traits?

Contrary to what most people believe, not every wealthy woman has a bitchy personality. Stop thinking Nollywood movies. The basic truth is every woman wants to be taken care of, even the ones with dominant, no mercy personalities. A woman wants to know that her man is perfectly capable of taking care of her, whether or not she has more money than he does. And if there is one thing guys know how to do, it is to be observant. And any guy that has his eye on a lady is pretty observant of her every move. Yup. He notices her quirks and habits and moods and reactions.

So, what have you noticed about her? How does she relate to people? Is she nice on particular days? Is she the loud, obnoxious type? Does she make sure people are well aware of how much money she has? Is she the type to run from attention? Does she like the simple things in life? There are a lot of questions you are going to ask yourself about her. Debunk that theory that people hide their real selves, they don’t. We choose whether or not we want to see them. If you’re honest enough, you will notice a lot of things and you will be able to make a sound decision about your affections for the woman in question.

If you have answered those questions above, honestly, you should be ready to answer this next one correctly.

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What Do You Want From Her?

A made woman isn’t waiting for you to strike gold and make your first million. This may sound intimidating, but it is the truth. She wants to know where you stand. She wants to know what you want from her. Money doesn’t heal a broken heart if you’re thinking in that direction. And you don’t want to end up on the ‘Men Are Scum’ list. What do you want from her? A fling, a stepping stone for your career, something worthwhile, or a chance to supposedly tame a wild, wealthy woman?

Knowing what you want before you fling yourself into the deep end will help you weather any nasty surprises that may come up afterward. And remember, underneath the layers of Marc Jacobs, Louis Vuitton and House of Tara makeup, she’s still a woman. She is a woman with wants and needs like any other red-blooded female. Or in her case, blue-blooded.

Now that you have answered these questions honestly, you alone can decide if you want to go ahead and pursue her. If you do decide to pursue her, I have something to tell you.

Do Not Make It A Competition

Do not. Absolutely not. Don’t even think about it. Yes. You are a man, you want to be the guy that gets her what she wants without batting an eyelash. Good stuff. But please remember that she has been doing stuff by herself, so she is not going to automatically hand over the reins. She’s going to need to adjust. And she may have this silly idea of trying to protect your sense of dignity by not asking you for stuff she feels you probably would be better off not buying. Don’t take it the wrong way. She does not want to hurt you, that’s how she sees it.

Do not try to impress her with silly stuff like that. She’s with you and that should count for something. Don’t become a workaholic because you’re wanting to beat ‘the standard’. She needs you, not cheques and alerts and fancy gifts. She has seen enough workaholics, man. No one is saying you shouldn’t get to the top of your game. Do it for you, not because you want to impress her or her circle of friends. The point is, whatever you do, do not make your relationship a competition. You’re better off without it.

Finally Brethren…

Ask yourself this important question: If I was the lady, would I pick me? Are you your type? No sir, she will not love you for who you are. Okay, lets clear things up a little. The problem is not your financial status. Do you have a feasible plan? Are you working on something? How do you manage the little resources you have? Do you take care of your body or you smell like a bad decision? No need to tell me the answers buddy!

Before you run off…

We would love to get your sincere opinion.

Ladies: Can you marry or date a broke guy and on what terms would you consider such guy?

Guys: Can you marry or date a lady far richer than you or would you rather stick to your “standard”?