If you're a man, you have to accept the fact that dating is an unfair proposition. Forget everything you've heard about economic equality; women expect you to pay. It doesn't matter if she makes twice what you do. It won't do a bit of good to complain about the hypocrisy, the entitlement mentality, even the downright greed of some women. This is simply the way it is. You're essentially in the position of someone who wants to play poker. To get a seat at the table, you've got to buy in.

Of course, like any good gambler you need to manage your money intelligently. Unless you're into making a statement (and the statement may not be what you had intended), it's insane to take someone out on a first date to a fancy restaurant and drop two or three hundred dollars. If you think that a lavish night out is going to guarantee you some tender affection later, think again. It may happen, but then again it may not. Chances are, the woman will resent the slightest implication that she's being "bought". A man's attitude toward sex should be that it is always appreciated, but never expected.

Men tend to be comfortable in bars, and instinctively assume that a drink or two will put a woman in a romantic mood. But first dates between total strangers (such as people who have met online) should normally be at a coffee shop. Financially, the worst that happens is that you blow ten bucks on a couple of lattes and never see the woman again. Coffee shops also offer the advantage of a quick and graceful exit if things are clearly not going well. The money you can blow in the upscale restaurant or cocktail lounge is bad enough, but wasting the night there with the wrong person is worse.

Even after the first date, you can get away with spending modestly without earning the dreaded label of "cheap". If she likes to cook, why not suggest she make a nice dinner and you provide the wine and dessert? Even if you offer to pay for some or all of the food costs, it's still a lot less expensive than having the same meal in a restaurant. (And if she hates to cook, or even takes offense at your suggestion that she do so, you're better off finding this out sooner than later).

Aside from what they're going to spend directly on meals and such, men have to factor in some indirect costs of dating. I can't emphasize enough the importance of looking good. Women may not be as hung up on men's appearance as men are about women's, but they definitely notice. The man who is in reasonably good shape, wears nice clothes, has a good haircut, and, in general, presents an image of health, fitness, and style, has a huge advantage over other men.

You may say, "But I see nice-looking women all the time with fat slobs". And that's true. But generally, those are married couples. The wife puts up with the husband only because she's used to him and doesn't see any realistic alternative. If she was meeting him for the first time, she'd run the other way. She's not unlike a person who owns a fifteen year old car that has dents, ripped upholstery, filthy carpets, and a crack in the windshield. If the car still runs, she doesn't even notice the damage any more. She'll keep it until it dies. But when she's buying a new one, she wants everything perfect.

It needn't cost a fortune to make the most of your appearance. Although gyms can provide motivation and a wide variety of equipment, they can be expensive. The truth is, you can get all the exercise you need for free, by taking brisk walks and doing pushups and stretches in the living room. (If you think you need state-of-the-art equipment to stay in shape, keep in mind that Herschel Walker, one of the greatest running backs of all time, never lifted weights. Throughout his entire career, he trained by doing pushups, sit-ups, and sprints).

You can keep your clothing costs in line by buying fewer, but better quality, items, and looking for sales. You don't need to spend fifty dollars for a good haircut; the key is simply to get one that's contemporary- looking but age-appropriate, and to get it before it's obvious that you need it. Good skin-care products for men are available in every supermarket and drug store, at reasonable prices. Once you get into the habit of looking your best, it becomes almost second nature.

As your relationship with a woman becomes more serious, you'll have to be prepared to spend some money on gifts. Women love gifts from a man anytime, and they expect them on the "obligatory" occasions---Christmas, Valentine's Day, her birthday. But don't cop out and get her a gift certificate, unless it's for a personal-care service like a massage or pedicure. Instead, learn to be comfortable in stores. I've found over the years that male shoppers get an incredible amount of attention and helpful advice from female salespeople. They love it that you're the kind of guy who cares about getting something for his special lady, and they'll knock themselves out to make sure it's appropriate for the occasion.

In between those special occasions, I strongly recommend giving small-but-frequent gifts, for no reason other than that you were "thinking of her". You can get a lot of mileage out of a ten-dollar container of skin cream or bubble bath from a nice store---something that makes her feel pampered. Of course, you don't want to do it so regularly that she resents it when you show up without a gift in your hand. With women, it never hurts to keep them a little bit off-balance.

©2008

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