Read the original Men's Fitness article here
Avoid awkwardness with these three rules.
It used to be simple: The guy paid for everything. This made sense at a time when most women didn’t work, or if they did, when they didn’t make nearly as much as men.
These days, things are more confusing. Some women will be offended if you ever hesitate to take your wallet out when you’re on date. Others will be uncomfortable if you spend a lot; a woman can worry that you think that she can be bought, or that spending money means you expect her to have sex later.
Use these three simple rules to solve the "who pays" problem.
For initial meetings, the "who pays?" problem is one to be avoided. Don’t take her anywhere overly expensive or try to use money to impress her. You’ll make most women uncomfortable, and even a gold-digger won’t sleep with you. Why should she? You’ve shown her you’ll spend money in pursuit, so she’ll want to keep that pursuit going.
When the time comes to pay, take out your wallet. Some women will fumble around their purse as if they are looking for money; ignore this. If she offers to contribute, tell her that she doesn’t have to; many times these offers are just for show. If she persists, then assume that she sincerely wants to contribute, and let her.
If paying for the first few dates creates an issue for you, choose less expensive dates instead of trying to get her to chip in for more expensive ones.
Rule No. 1 doesn’t apply if she creates an awkward situation. On a recent first date, I opened a tab and we ordered a couple rounds of drinks. Then, without asking my opinion, she ordered a $300 bottle of champagne. Waiting for the bill for this was like listening to a ticking time bomb.
I sometimes tell this story to clients and ask what they’d do. Men who say that they would pay for the champagne are men whom I know will need extra training. The ability to recognize when to set boundaries and how to communicate those boundaries is one of the most important factors in being attractive to women. Women don’t want a pushover.
In fact, many women will consciously or subconsciously “test” you with various behaviors that push the envelope, just to see how you will react. It’s not generally as blatant as ordering an expensive bottle of champagne and doesn’t have to revolve around money, though it can.
Either way, you should never accept this sort of behavior. Even if you could easily afford the cost, you should value yourself more than to let a woman treat you like an ATM. On the other hand, don’t react emotionally. In this example, once I set my boundary, the woman told me she intended to pay for the bottle herself, and did. I’ll never know if that’s what she always intended, or if she just started backpedaling when I called her out, but hey, it resolved the situation.
If she hasn’t offered to contribute to anything by the end of the third date – not dessert, not the valet, not the tip, not even a round of drinks – then she probably never will.
That may be OK with you, or it may not. Some of my clients like taking care of their partner. Others find it offensive. I can’t tell you what to like, but if her behavior does happen to be a dealbreaker for you, throw the last chance “Hail Mary” pass first. Go on a date with a little bit of cash, but “forget” your wallet. If she says she’ll take care of things like it’s no big deal, then the situation might be salvageable. If she suggests going to get your wallet or expresses any reluctance or even dissatisfaction, then you know that the two of you won’t be compatible.
Congratulations. You just saved yourself a relationship full of drama and conflict.