Old Fashioned Dating Rule 2: The Man Plans and Pays

This is one old fashioned rule that I think really does still apply today. For all that women are equal, women still love the men who pay. It shows her that he is a gentlemen and women still crave gentlemen. Now let me clarify here. I’m not necessarily saying pay every time and I’m certainly not saying pay beyond your means in an attempt to impress her. I am saying that for the first date, you, the man really should plan and pay.

You’ve met the woman and hopefully you engaged her in enough conversation to learn some of her likes and dislikes. This is why conversation is so important. If you have learned some of her likes it makes planning that first date so much easier. If she likes spicy food then taking her to a Thai restaurant may be an option. However, don’t do anything you really don’t like. That will give her the belief that you enjoy that activity as well and she will have an expectation that the two of you will continue to do those things. If you learned she likes opera and you don’t, don’t take her to an opera on your first date.

Tip #1: Planning

You’ve learned a little something about her so what do you plan? Try to find something that is enjoyable for both of you. Plan something that is non-threatening. By this I mean make it public. She might not know you well enough to be comfortable dining at your place. Save that one for later.

Keep it simple. Don’t try to plan anything too grand on a first date. First dates are about getting to know the other person. If you try for something too grand and it falls through she will be disappointed. However, if you are a ‘grand’ kind of guy, make sure you have a backup plan just in case it does fall through. “The smallest deed is greater than the grandest intention”. This is especially true on a first date. The last thing you want is to disappoint your lady on your first date.

Plan to pick her up, and plan how the evening will end. If you’re going for dinner and everything is going great then have a secondary plan. Perhaps you could go for a walk after you’ve finished eating or perhaps a movie. If the date is going well you don’t want to end it too soon. You also don’t want an uncomfortable date to drag on too long. A date can be ended after dinner.

So have your plans in place. Keep it simple and have an exit plan and a plan to extend the night if it’s going well.

Tip #2: Paying

There really is an etiquette around paying. If you want a woman in the ‘friend zone’ then by all means suggest going dutch. If you want a woman for a date and a potential partner you really do need to pay on the first date. So while you’re making your plans, make sure you account for everything including gas and parking money on top of the cost of the meal or activity you have planned. Have enough money to cover an extended date in the event that if the two of you decide to go for a walk and then stop at a pub for a drink, make sure you have the money to cover the drinks as well.

Now that you’re out on the date there are ways to pay that don’t make it awkward or uncomfortable. If you choose a restaurant, once you’re ready to request you bill, make sure you speak up and ask for the complete bill. If your server brings the bill, without making it obvious simply slide the bill towards yourself and keep it beside you until you’re ready to pay.

I’m going to give you a warning here. It’s okay to check the bill over quickly for any obvious mistakes, but don’t spend a lot of time scrutinizing the bill. The reason why is that women don’t like cheap men. If you look at the bill for too long it gives the woman the impression that you really didn’t want to spend that much on her, that you’re cheap. If you do notice a mistake on the bill don’t make a big issue out of it. Don’t complain to your date. Simply call the server over point out the mistake and ask her to correct it. Then when it comes time to pay do so without making a huge point of it.

Old Fashioned Rule #2: The Man Plans and Pays

I say yes that this rule still applies. At the very least, for the first date, it shows the woman that you are capable of making decisions, that you are in control, that she can rely on you. It also shows her that you are a gentleman.

Plan carefully. Try to plan something you know she likes or is interested in. Have a plan to end the evening and have a plan to extend it if it’s going well.

Pay. Make sure you can afford the evening you have planned. Pay for everything, but keep it discreet. Don’t make a point of it. You don’t want to be obvious. If you are, the woman will know that you are only doing this to impress her and she’d much rather get to know the real man and not the showcase man.