Ladies, Meet Benjamin.

I have had many women (and men actually) ask me when and/or if it is appropriate for a woman to pick up the check for a date.  This is always a tricky subject and usually one of the most awkward moments of the night is when the server puts the bill between the couple on a date and you both stare at each other wondering who is going to grab the bill. Side note: Let’s hope that part is the only awkward moment of your date.

Regardless, I have created some personal rules that I have been following when dating for when I should pay for the check.  Please feel free to make these rules your own guide to financial obligations when dating also.

First Date

My general rule of thumb is that whoever initiated the first date should actually pay for the bill (dependent of gender).  However, I do think it is a very chivalrous and gentlemanly act for the man to offer to pay for the first date. Ladies should always offer to go dutch and split the bill, but most men will refuse this notion regardless. Trust me in the fact that just offering and not assuming the man is paying goes a long way, though.

Second Date & On…

This is where I get a little disappointed in the female population.  A lot of women are under the impression that the man should always pay for the date. 

Ladies…it is the 21st century. If you want to pull the “man should always pay for a date card” then you might as well think that women should not be allowed to vote, provide for their families, or become CEOs of organizations.  We live in a world where women are making the same or more in salary than some men their own age so unless you are dating Joe Millionaire I think it is only fair to pay for the check every once in a while.

I want to be clear that I am not saying a woman should pay the majority of the time. I am just saying that the man should not have to be stuck with the financial burden on every date. My general thinking is to either pay every other date or if the man has paid for three of four dates in a row, make sure the next one with him is something extra special that the woman sets up and pays for.  If he has taken you to four expensive dinners, the movies, and a baseball game with no unanswered payment, just make sure you reciprocate with a nice dinner and/or something special (and I don’t mean pizza and an On Demand movie).

I also believe it is an appreciated gesture for the woman to offer to pay for her portion of the check on every date, too.   Like I said, most men will refuse this appreciated notion anyways. However, I understand that is not a universal thought among women.

My fellow lady friends – when you are out with a George, Thomas, Alexander, Andrew or Benjamin don’t forget to bring their money counterparts on the date with you.

I hope you found this financial advice helpful – you can put it on my tab ;)

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