Dating Advice – Should The Man ALWAYS Pay?

Last week someone asked me a really interesting question. She asked me if a guy should always pay when dating a girl? And my first thought was, “GREAT FREAKING QUESTION”. Then my second thought was “Hell TO THE NO”. Hell nah the guy should not always pay.


Well because as we all know, with dating things often don’t work out. That’s just how it goes. I’ve been there and you probably have too. So now imagine how the guy feels if he paid for the first, second, third, and fourth dates and then you guys decided to go your own separate ways. Ma man would feel like crap because he probably invested about $600 in getting to know you and that money just went down the drain. He could have used that money to pay down his student loans – like me. He could have invested that money in the stock market. Or he could have used that money to help his family with something. And, yes, you can EASILY spend $600 in New York City on four dates.


So if things don’t work out, what is the guy left with? Yeah, that’s right, nothing. Nada. Zilch, except for a $600 credit card bill, a wounded ego, and a wounded heart.

Look, I know that there are quality girls out there that won’t let a man spend all this money if they weren’t interested. And I know that there are many girls out there that won’t let a man pay for all four dates. But I also know that there are a lot of girls out there that ain’t got no problem in letting a man take them out well knowing that things aren’t going anywhere.

So I think in this scenario, there’s enough blame to go around on both sides because ma man probably knows deep down that she ain’t feeling him but he decides to try anyways.

So to all ma fellas, before you go opening your wallet, text, talk on the phone, facetime, and then text some more before hanging out.

Because you’ll know quickly if there is a connection or not.

And if there isn’t a connection, cut your losses early and use your money for other things. But if there is a connection, try and do things that don’t require much money like a coworker tells me. A useful rule of thumb here is to stay away from alcohol. Bars, lounges, and clubs are usually where the big spending takes place.

And to all ma ladies out there, pick up the tab every once in awhile. I would suggest picking up the tab no later than the third date. And if you REALLY REALLY REALLY want to wow a guy, pay for the first date. I’ve been on a ton of first dates, and only TWO girls have actually paid for that first date. And both of those girls, I ended up taking very seriously and I’m still friends with them till this day after many years.

Why? Because girls hardly ever do that and her paying for the first date clearly communicated to the kid that she taught that I was AWESOME.

8 Comments - Add Comment