Check Please!

dinner check




You’ve been emailing for about a week. What a hunk! You shopped for the cutest little dress in the mall, and finally here you are. Corner table, candle glow…where did the time go?


The waitperson brings the check and puts that brown leather holder right in the middle of the table. The time of reckoning is here! Nobody moves a muscle toward it. Uncomfortable much? Of course it is!! It is a “defining moment” for many women and though it might come as a surprise to women, guys have their own dialogue going on in that cute little head of theirs. Wanna know what it sounds like??


“Well, women want to be ‘liberated’? This is what it looks like!”  “She makes as much money as I do. Why should I pick up the check?” “If I pick up the check, she is going to think I expect her to sleep with me. I learned my lesson from the last woman I took to dinner.”


And what is she thinking? “If this man is really a gentleman, he will pick up the check.” “If he doesn’t pick up the check, this is it for HIM.” “What? He isn’t going to pick up this check??”.


A dinner check, and even who pays for a cup of coffee can set the tone for everything that happens or doesn’t from that moment on. Why is that? Because we have attached so much meaning to this gesture and never really talk about it before we go out with someone.


Men have had experiences with women who HAVE taken advantage of them. Clients have told me many times about women they met online who will only meet them for dinner, order expensive wine and entrees and then ditch them…truly the sad definition of a “Dinner Date”.


There has always been confusion about what it means sexually when a man wines and dines a woman. There are also leftover emotions for Baby Boomers who turned the world upside down during the women’s movement. Women struggling over wanting to be cared for/cared about by having a man pick up the check. Men left without clear rules or roles now have whiplash. Picking up the check can be an opportunity for passive-aggressive anger or a genuine moment of not knowing what-the-hell to do now.


What can you do to make your next date free from this “deal-breaking” ending? Men…you can let her know “Dinner is on me”  if you genuinely feel that you want to give her that gift. Note, I said “gift”, not “expectation”. If you want to “go Dutch”, tell her that ahead of time, and share honestly your feelings about this arrangement.



Women…men do not read minds! I know we think they do, but believe me when I tell you most of them always need to be told what you are thinking. Don’t assume they will pick up the check (What’s with that???). Offer to pay your part. Bring cash with you and put down your part of the bill on the table. Allow him but do not expect him to say “No, let me pay.”


Know your own beliefs, attitudes and values about money and be prepared to accept that he/she may have very different ones from yours. Though some would say the first date sets the tone for the relationship spending patterns, I don’t buy it. If the relationship continues, it is crucial that you talk about money. I speak from experience when I say if those values are not the same it can mean a great deal of struggle and sadly in some cases, make the relationship impossible.


Here’s hoping if you follow this wisdom you will see him/her again but even if you don’t, both of you will have better digestion!

Bon Appetit !!



1 Comment

  1. ExitAisle on January 12, 2016 at 9:55 am

    Almost no topic raises more hackles than money… my own rules were always…

    no more than coffee for a first meeting because more than likely it will be the last…

    before spending more than coffee costs have the discussion and make clear your preferences…

    my preference is to split the expenses… I never saw reason at this age and stage of life to carry an unfair burden of relationship expenses… more than once this caused a parting and I considered that a good outcome…

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