There is no hard and fast rule on how generous or how practical with money the guy should be in life in general and in his interactions with women who he is meeting and dating specifically. My observations suggest that being too generous or reckless with money is just as detrimental to attraction as being stingy. Being a cheap guy communicates to a woman that you either don’t like her enough to enjoy treating her, or that you are just cheap in general. She will also conclude that you are going to be tight-fisted down the road, if you start seeing each other and developing a relationship, refusing to enjoy your life as much as, in her opinion, you should be.
Being too generous with a woman, especially when you just met her is also a problem. It will consciously or subconsciously communicate to a woman that you are either so desperate for female attention that you are eager to buy it, or it will place you in the friends zone, where you take the role of the provider or a “sponsor” instead of being a date or lover that you should be.
Generosity and cheapness are relative terms, as different people have different standards and expectations when it comes to money, spending, and dating. However, being a guy who is petty is an absolute no-no regardless of how you choose to use your money. No woman is attracted to a petty guy who counts every penny. The other day I was sitting at a restaurant with a friend. A guy and a girl were sitting at a table next to us. They were obviously on their first date. When the bill arrived, the guy pulled out his calculator and started struggling to figure out the exact percentage of the tip that he should leave. I looked at a girl and smirked. She looked at me and rolled her eyes. While that might not have been a deal breaker for her, I would be very surprised if they actually went out again. Even if the reason the guy pulled out a calculator was because he was struggling to figure out the proper tip, it still looked really tacky. The same applies to splitting a bill. Generally, during the first 4-5 or even more dates you should never split a bill. Treat the girl on your first and second date. If you go to two places, i.e. to dinner and dessert, buy the dinner and let her buy the dessert. If you treat her 3 times, let her treat you the fourth time, but don’t sit there and divide the bill between the two of you, as it’s extremely unromantic.
One common reason that guys come across as cheap or petty is because they think they have to take their date out to an expensive place, which is out of their budget. Then, when they arrive there, the guy tries to be very careful about what they order. He is likely to resent a girl who orders an expensive dish or a drink. However, there is no one good reason to take a girl out to a place that you don’t feel financially comfortable going to. You are much better off going out to a place which is less expensive, but where you also don’t need to worry about ordering something you can’t afford. You will then enjoy your meal and your time with a woman instead of worrying about the bill.
