Everyone has a different relationship with money. Don’t assume that the guy you’re dating looks at a dollar bill the same way you do. The topic of finances is not something you should discuss too early in the relationship, and don’t judge a guy by whether or not you think he has money. Don’t be a gold digger! It’s shallow, and guys don’t want to feel used. When you bring up money on a date you will either sound like you’re bragging or like you’re broke. It’s a double-edged sword. There are ways to let the other person know you’re financially secure without saying a word or showing off.
Never discus money or the cost of anything in dollars and cents during the initial stage of connecting with someone. Consciously avoid talking about it. Whenever the question of the bill arises-the amount of a charge, the cost of the tickets, the price of gas, etc. —just be generous and gracious. Whether he picks up the tab for a two-hundred-dollar dinner or a two-dollar ice-cream cone, thank him very sincerely. Offering to pick u the tab, split the bill, or leave the tip will go along way with a man. If you offer to chip in and he doesn’t let you, just thank him.
But if he lets you pick up the tab or splits with you and you just started dating, it’s not a good sign. It could mean he’s cheap, strapped, or just not interested-none of which bodes well for you. If he lets you leave the tip he might just be testing you to see if you would put any skin in he game. Men want to be generous because they decided to be, not because it is expected. Guys can easily be rubbed the wrong way by women who expect generosity. It immediately sends red flags and raises the gold-digger alert. This is why showing appreciation and making the offer to contribute go a long way.
Often women find themselves in a position where they make more money than the guy they are dating. If you want to do something nice for him treat him to a date, do It nonchalantly and discreetly. Men have to feel like they can provide, and for some men it can be emasculating if they can’t spend money on a woman. You should really appreciate it if a man with limited resources goes out of his way to plan an inexpensive, but thoughtful, date.