A story of an “old school” date…


Happy Sunday. I was hitting a bit of a writer’s block” when I decided to share an “old school” dating story. This one was funny enough to make it onto a major NY City Radio Station about 20 years ago. You see, I am a “long time” dater. I have had plenty of “long-term relationships” over the years to include a failed “short-term” marriage. I think over the long-term I have spent more time dating than most, making me what I often refer too as a “professional dater”. If there was such a thing, I most certainly would have earned my PhD in dating by now…

So I was 23. I have 2 terrific girlfriends (who are married now, one is in London, and one lives in my town) who were my “partners in crime” in my 20’s. We relished in the notion that every weekend we would be “out in the big City”. And boy did we paint NY City red, blue and all the colors of the spectrum. On this one particular Friday night, we were invited down to the Park Avenue Country Club for an open bar event. I cannot even tell you who invited us, but I do remember the night was “on the house” so as broke “twenty somethings” we were most happy for the opportunity to drink for free. It was at this Country Club that I met him. Michael from Manhattan. A boy about 5 years older than me and very eager to take me out on a date. Due to all of this free liquor I was very well intoxicated by the end of the evening, so I agreed to a date. I lived in Thornwood, NY at the time and he was more than willing to come up from the City via Metro North and take me out on a date.

We spoke by phone a few days later and made our plan. I was to pick him up at the train station and we were to dine at the lovely chain restaurant I shall not name, but possesses a favorite day of the week in its name. I often picked this establishment in my twenties, because not having cell phones back in those days, the ladies bathroom possessed a pay phone which was most handy should I have needed to make a phone call to a girlfriend for a quick escape plan.

The big Friday night came, and as soon as I collected him off the train I knew before he even got into the car, that he wasn’t my man. After all, he wore a fake “pleather coat” with a fake fur collar! YUCK! A “fashion don’t” in those days and I’m quite sure even by today’s standards. But I decided, like I always do, to grin and bear it. The first major “no no” he did was move my gear shift in an attempt to be playful. Being a City boy, he didn’t understand how to drive a car, nor did he understand that moving my gear shift with me not paying attention, could have shifted us into neutral and made us roll back into another car. Needless to say, I firmly educated him to “never” touch my gear shift. He got the message.

At the restaurant, I was ready to go home. I decided to order something fast and simple so I could get him back on that train as soon as possible (why coffee dates are so much better as I have learned). I ordered a pasta and a glass of water (in those days my entire bill probably came to about $10). He ordered steak and shrimp and 2 strong drinks. Clearly he was having a better time than me, taking his time on the meal. I almost made my “get a way” phone call in the lady’s room when the check finally arrived at the table. Upon seeing the check, I quickly handed him a $20 bill and stated “this is all I have”. Now as you know, if I hand a boy money for the bill on a first date, I am most definitely not interested in seeing him again and I most definitely did not want him paying for my meal thinking we were going to see each other again. And I was quite certain that by stating “this is all I have” that I would get a $10 bill change from him. NOPE! He took my $20 and put it in his wallet. He said “thank you”. That was that!

So I quickly deposited him at the train and never saw him again. However a few months later, a major NY City radio station was advertising for “worst dating stories”. I couldn’t help myself. I called and told the story and when the DJ put it on the air, he yelled out “Michael, in Manhattan, give Leslie her $20 back ya cheap bastard!!!!” I did record this on an audio cassette tape and believe it is still in the bowels of my closet in a box somewhere.

So remember women, keep your money in your purse…Unless you REALLY don’t like him….Keep small bills on hand…never expect change.

Hope you are enjoying this gorgeous weekend. Thanks for reading…


4 thoughts on “A story of an “old school” date…

  1. Maybe he saw it as reumbursement for his metro travels. LOl. I dont miss dating by that i mean the “shopping” phase not the “in it, dig you, want you” phase. Root canal has more appeal. Ive been on those too soon for dinner dates where you wish you could fake choking so someone would pull you away from the table and literally save you!

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