Check Please! …Who Should Grab For It When It Arrives?


This has probably been a debate since the beginning of time. The million dollar question?

Who is responsible for the check at the end of a date?

Now I don’t claim to have the correct answer or to represent the opinions of all singles. .. so as a disclaimer don’t take this as Gospel!

In relation to this topic many people have debated on whether or not Chivalry is dead. Now I wouldn’t go so far as to say that it is dead, but I don’t doubt that it has been in and out of a coma for a few years. lol

The reality is that lot of men just aren’t chivalrous anymore. In addition, a lot of women aren’t requiring OR being very deserving of chivalrous behavior. The standards are just no longer there.

Now do I believe that there are rules in regards to who pays for a date? Of course I do!

Ultimately, I believe that this topic/situation/dilemma can help to determine the compatibility between two people. Let’s explore how…

I personally believe that a man should usually plan, execute and pay for a date with a woman he is interested in getting to know. A woman’s concern should only be seeing whether or not she is free on the date he mentions, choosing an appropriate ensemble, making sure she’s ready when he arrives so that he doesn’t have to wait & being the best company on whatever adventure the guy has decided to take her on.

I think that the art of “courting” has long been lost within this modern generation of situationships and the fear of coming across as “thirsty”.

Either men don’t know how to court women, women don’t know how to be courted. .. or people are just too lazy and accepting of mediocre displays of interest to realize that we are taking all of the fun and beauty out of dating.

Now what I am about to say will probably spark the verbal opposition of at least 90% of women, but once I explain maybe some of you may get where I’m coming from.

When I go on a 1st date with a man and the check arrives… 9 times out of 10 I offer to pay for my own portion of the date. It’s always interesting to see what happens next. So much so that I sometimes have a little bet with myself about what kind of response I think he’ll give me.

I do this for more than one reason.

1. I want to see his initial reaction. .. as alot of men go through the “Is she just here for a free meal” thought process.

2. I want to show that I am willing and capable to fund myself if the moment requires. Ya know SOME men still feel like you owe them something after a little meal. Shame.

3. And ultimately I do this to see if the guy is actually going to allow me to pay for my own meal on a date he asked me on. You’d be surprised at how many men actually have said to me “You sure? .. Okay cool.” And with a sigh of relief they let me pay for my own sh*t.


I’d like to say that I never went out with them again. Which is exactly what happened with all but ONE of them.

But that one well… he was extra FINE ya’ll and just beautiful to look at so I let him make it lol. Luckily, I think he was just nervous that evening because I never had to pay for anything else when I was with him. So I try not to count him in that list. ?

So anywho I think the number of dates you two have been on together, who extended the invite and the nature of the date/relationship determines who should pay.

Here is my version of the “Date Pay Rules”:

1. Men should always pay for the 1st date.

Exceptions: If the woman initiated the date then she should offer to pay & be prepared to. Although. .. I think a quality guy should offer to cover instead… especially if he truly wanted to be there with her. I also PERSONALLY believe that a woman should allow a man to pursue her & ask for her time, not the other way around. But… that is the traditional side of me so that only applies to those of you who prefer that style of dating.

2. Going dutch is perfectly acceptable, especially if and as long as it has been discussed and agreed upon beforehand.

3. A woman SHOULD insist on paying for at least one date once it is clear that the relationship has progressed past pursuit & is weeeeellllll within the courtship phase.

Note: I think women should approach this very delicately. You should be able to show a man that you enjoy his time & that you are prepared to be an equal in your romantic interactions with each other. This must be done in balance because you do not want to shift the courtship and sell yourself short. A dinner tab or movie ticket on occasion is okay as long as he still continues to court you in addition to your generosity. A real man will recognize and appreciate your efforts without decreasing his in response.

4. Once you’re in an official relationship it should be completely give and take. I still feel that the man should pay MOST of the time, but at this point women have a responsibility to be an equal partner in this (and all) aspects of the relationship.

Now, aside from all of that, I get the fellas’ pain. You can waste a lot of money paying for dates with women you have no chemistry with and never want to see again. If you go on 2 bad dates a week… spending an average of $60 per date… you can easily waste an upwards of $480 in just a month!

So yeah, I get it.

This is why I always advise guys to plan low commitment, inexpensive 1st dates. Especially if, aside from a few brief phone conversations, you don’t know much about her at all.

Lunch dates are perfect because they are on a time constraint… so if she’s boring, loud, rude or not as cute in natural light then all you have to give her is an hour of your life and then you move along. Both of you go back to work and Voilà you’re done!

Coffee shops, book stores and even “Hey let’s meet up and walk around the Upper West Side.. or Central Park” are also great ideas. All are pressure free and low to no cost. In addition, they make CONVERSATION the heart of the date which proves or disproves chemistry and compatibility!

So ladies… learn how to be courted and when you do, enjoy every minute of it. Put those pocket books away and let that man show you just how much, or how much he is not interested in you. Sometimes if we just sit back and submit ourselves to the traditional roles of dating when can weed out the losers quickly and give more of our time to the quality men out there.

Fellas… stop thinking that you have to have a driver pick her up and bring her to the restaurant that you rented out for the night so that you could cover it from wall to wall with roses. It’s not that deep! Lol

Although that is beautiful. .. AND it ain’t trickin’ of you got it, save the grand gestures for future dates. You don’t even know her yet… make sure you at least can tolerate her before you spend all your money on a date with her.

Most women (I said MOST) have no problem at all meeting you at a coffee shop or book store for a 1st date.

One guy invited me to Central Park for our first date and we sat on a bench and talked for HOURS! It was one of the most authentic dates I’ve ever been on and it was free. If the 15 lb rat wouldn’t have invaded our personal space we probably would have stayed there all night talking and vibing with each other. Lol

So be smart about these dates and respect the rules. They can make or break the relationship before it even gets started. Trust me! Lol

Happy Dating! 😉

Did this post hit home? Let me know!