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Who Pays

Some women are insulted if men always insist on paying. It may make them feel as if they are being bought or patronized, as if they can't afford to pay their own way.

you should always pay...

On first dates

First impressions are important -- on most first dates, your best bet is to make the first move when the bill comes, and if she shows no sign of resistance, go for it. This goes not just for the very first date, but throughout the early stages of the relationship. Paying for things is not just the gentlemanly thing to do, it also indicates that you are responsible, steady and well-established. Women like that; it helps them decide whether or not you are relationship-ready.

If you asked her out

A good general rule when it comes to these situations is to ask yourself, "Who asked who?" If you instigated the date, then you will be expected to pay. In fact, it's good to be prepared to pay, regardless. Nothing looks more pathetic than a guy's sheepish expression when he doesn't have enough money with him to cover the charges; and in today's world of credit and debit cards, this shouldn't be an issue.

On special occasions

For special events, such as your anniversary, her birthday, holiday dinners or even just to spontaneously celebrate her achievements -- like being hired for a new job or getting into law school, for example -- you should offer to pay. First of all, it makes you appear gracious and classy. Second, it's a great way to show her how proud you are of her. Just remember that the key is in the delivery; don't make a big show of your largesse by letting her know how much a meal cost. What a tacky move! Simply smile and say, "This one's on me, honey."