Hazards of Mid-Life Dating

In the Beginning

Dating is very simple when you’re young; there isn’t any personal baggage involved. As we get older things happen that change the way we look at life. I myself got married kind of young, my new wife was only eighteen and I was five years older than her. I met her when she was sixteen and she began planning our wedding almost immediately. In those days that was considered normal. Most people at that time just wanted to get away from their parents; marriage seemed like the best way to do that. Although our marriage wasn’t made in heaven and we never quite got along, we still managed to stay together for thirty years. Arguing constantly will take its toll on a marriage; after a while it just seemed like one big thirty year battle, one argument leading into the next like chain smoking, with the same inevitable conclusion ; the death of a marriage. I built the coffin and she nailed it shut.

On my first day of freedom I began searching the newspapers for a place to go where I could possibly meet someone “special”. I wasn’t going to sit around feeling sorry for myself; I would take the bull by the horns. I managed to find a social event to attend that same evening. A little dancing, a few beers and all would be right with the world again. It’s been thirty years but it would all come back to me; I was sure of it. One thing I noticed right away as I entered the social gathering, the women were much older than I remembered. Of course I was still twenty in my own mind, thankfully there wasn’t any mirrors around just the one attached to the ceiling, it was called a disco ball. I immediately headed for the bar area to begin the process of inebriation. I sat next to two women who were also trying to get inebriated. I ordered an Amstel Light from the lady bartender; laid 2 dollars on the bar and waited thirstily. I glanced over at the woman seated next to me at the exact same time as she stole a glance at me; she smiled. Five dollars more sir I heard the bar lady say. Seven dollars for a bottle of beer? Dating was going to be expensive.

I gave the bartender the extra five dollars plus a three dollar tip: I didn’t want the lady seated next to me to think I was cheap. My first mistake. I sat there staring around the room trying to get acquainted with my surroundings when I felt my lap suddenly become very wet. “Oh my god, I spilt my drink” said the lady sitting next to me, “I’m so sorry, I’m such a klutz” I jumped up and looked down at my crotch area; “You have great aim” I said with a laugh. She offered to pay the cleaning bill but of course I declined and instead offered to replace her drink. My second mistake. She didn’t decline and ordered something called a Mojito; fourteen dollars please said the bar lady. Does Mojito mean gold in Spanish?

Her friend that was seated beside her somehow disappeared and now my new best friend was yakking it up pretty good. She was on her second Mojito and I could see that the bottom of her glass was arriving very quickly so I said “want to go for a drive”? Dumb question but I was running out of money. She leaned over and whispered in my ear “let’s go to my place”. I grabbed a napkin and wiped my ear and said “great idea”. The trip to her apartment was uneventful; she lived on the top floor of a four story walkup. “Its good exercise “she said as we finally reached the fourth floor landing. She took out her key and unlocked the door. I headed straight for the couch. She excused herself and went into the bathroom.

I perused the living room from my seated position and noticed some really old looking family photos. The pictures looked like they were from the nineteen forties. She told me she was 49 years old; may have to rethink that I noted. When she emerged from the bathroom she was adorned in just her underwear, your basic full breasted bra and tiny panties with leopard spots on them. She said “are you excited”? She proceeded to turn around very slowly to give me the full effect. She then took hold of my hand and pulled me from the couch and into the hallway that led to her bedroom.

I sat on one side of the bed and watched as she began to dismantle herself. Her beautiful black shiny well coiffed hair came off first leaving just some grey stubble. She put the wig on the dresser very carefully attaching it to a Styrofoam head with a face that someone drew on with a magic marker. Next to be removed were her lower row of beautifully straight gleaming white teeth. Again she very carefully arranged them in a jar of gorgeous aqua blue liquid that reminded me of Bermuda where my X wife and I spent our honeymoon. I was beginning to wish I was back there with my wife. Then came the really depressing part. Her bra came off along with her boobs. Falsies, in this day and age? I had this strange feeling that I was going to bed with a bald headed toothless old man. I kept thinking to myself as she took herself apart in front me, she must have done this many times before in front of other men because she had no inhibitions about it. She even seemed proud that she was able to coax me into sharing her bedroom with her.

In The End

Well I was getting out of there somehow or other. She said “take off your pants, what are you shy?” Yeah I’m shy I said, scratching my head, give me a few minutes to digest all this. She said “well don’t take too long because I’m really horny” and she sat on her side of the bed just staring at me. Suddenly God intervened, the phone rang. She jumped up and ran into the kitchen. That’s it, I’m out of here. I put my shoes on and grabbed my jacket. I peaked into the kitchen area and saw her reflection in the kitchen window. She was seated on a step stool next to the phone talking and smoking a cigarette. As I sneaked past the kitchen doorway I heard her say to the person on the other end of the phone something about me being gay. A small price to pay for getting out of there with my libido still intact.

Comments greatly appreciated.

Comments 8 comments

loren866 profile image

loren866 4 years ago

It was a great story and a good lesson to be learned.


Leesleez profile image

Leesleez 4 years ago from New York Author

Thanks for commenting


Glenn Stok profile image

Glenn Stok 4 years ago from Long Island, NY

As I started reading I was thinking about mistakes I've made, such as offering to take a lady out to dinner at the first meeting, only to have her order everything on the menu. But as I continued reading, I never imagined that your story would take a turn for the worse. Especially the way it happened. 

Very well written and humorous.  You built up the plot and then you sprang the surprise.


Leesleez profile image

Leesleez 4 years ago from New York Author

Actually she ( or was it he) sprang the surprise. Thanks for reading.


Ann 4 years ago

Saved by the 'bell'


Patti 3 years ago

I'd like to say that this could only happen to you, but I've heard a lot of dating horror stories in the last few years. Great, well-written story.


Leesleez profile image

Leesleez 3 years ago from New York Author

Thanks Patti. Actually I left out the best part but no one would believe it.


ralph-barclayweb 2 years ago from wantagh, ny

Whether fact or fiction - you tell a great story, with lots of humor, and vivid descriptions.

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