Be Cheap in the Beginning

by Jake McMillan

I believe strongly, as a guy, that we should be cheap when starting to date someone new. I know I am in a minority when I say this.

Many women and men believe men should pay for women on the first date and that it should be men who should woo their lady with trips to nice (read: expensive) restaurants and shower them with gifts. This is all wrong and I’ll explain why.

No matter how passionate and intense the romance is at the beginning of a relationship, the reality is that this will fade and at some point or another your partner will ask you why don’t you take her out to nice places anymore or hardly ever buy her flowers, etc. It’s the same principle as when Harry tells Sally in ‘When Harry Met Sally’ why he doesn’t take his girlfriend to the airport at the beginning of the relationship:

Harry Burns: You take someone to the airport, it’s clearly the beginning of the relationship. That’s why I have never taken anyone to the airport at the beginning of a relationship.
Sally Albright: Why?
Harry Burns: Because eventually things move on and you don’t take someone to the airport and I never wanted anyone to say to me, ‘How come you never take me to the airport anymore?’

By being cheap in the beginning, it means when you do eventually make an extravagant gesture now and again it has more meaning. It’s all about managing expectations. If you spend a lot on them in the beginning, you are setting a dangerous precedent which you will ultimately fall short of, whereas if you are cheap then their expectations are low and you can only exceed them.

Therefore, being cheap is a good strategic move relationship-wise. It’s also, let’s face it, good for your bank balance.

If you’re doing a fair bit of dating and paying for all these dinners and taking women out, it can get damn expensive. You can justify the expense for the woman of your dreams, but you can’t for all the others you’re wasting your hard earned cash on.

The one down-side in the being cheap approach is that women don’t like it and may not want a second date if you appear too tight-fisted. That is why you have to start managing their expectations even before the first date begins. I always tell women I’m about to go on a date with that I am cheap and that they should expect to pay for their own food.

I hope they don’t think I am joking?

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