A Cougar’s Tale: I Wasn’t Smart Enough To Date You When I Was That Age

I assumed our age would make a difference, but no matter the clues I gave, you still asked me on a date. When I finally got up the nerve to ask your age and my response was “Fuck”, politely placed under my breath. And you, just smiled. No matter, you were a delight and so I agreed to see you again. 

Seeing you again was like a breath of fresh air. I also liked how you enjoyed a night at home. Movie, dinner couch time. One of the best. Dinner, drinks, a movie at home. 

The kicker…what got me going for you, was you wanted to watch baseball with me. That meant more to me than anything. 

Of course we ended up for the same team. Me for the Indians because I was a respectable Cardinals fan and the Indians had been your team since childhood. I haven’t had anyone to watch baseball with since Cleats. And through the post season, we watched your team make it to the World Series. 

It wasn’t their year, but in the end I enjoyed every moment of us watching and talking about baseball with you. And, basketball. Can’t wait for March Madness. 

Then there was the election. Still the election. What a rollercoaster? Again, our team didn’t win. You were so invested in her campaign, even so much more than me. We licked our wounds like most of the country and prepared for “the shit show” as we call it now. 

We finally discussed what our expectations were for the relationship. Mine were to enjoy the time with you and see where it goes. Yours were the same. Except, your final intention was to get married and have a family, “with someone who doesn’t have any children. I want my own family.” Once I realized the romantic relationship was finite, I checked out, and you did too. I totally agree with you and know when I was 25 I wouldn’t have imagined ending up with someone 12 years older and already had children. But when I was 25, I would have passed on you sadly. 

I was never as mature as you are now at 25. Never as motivated and driven. Never stuck to my beliefs and instincts. It’s terribly sad to realize, but our timing was off. I’m not sure who is ahead and who is behind. Even a 25 year old Sally would have missed you completely. 

I always wondered why women and men go younger? I know now. It’s a piece of our past we enjoyed. My family had already began at 25, but that time of life is amazing. “It’s all happeneing” some say. For you it definitely is. 

This experience has taught me not to count out any age guy. You may remember that night we talked about “how old could you go?” You asked me so I told you when I was 36, I went out with a 58 year old. You were shocked. 

“That’s too old.” He said.

“What?” I said. “It’s just 22 years older.”

“Yeah”, you said. “That’s a bit much.”

“Yes, we are aware how you feel on the subject.” 


Here’s what I am most thankful for. My new friend. We didnt break up, we evolved. We still talk daily, now that the romance is gone. We can even hangout and you are almost in the bromance, if you want to be. I enjoy you so much…so much more than I ever did when we were dating. And believe me, I enjoyed you then. 

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4 thoughts on “A Cougar’s Tale: I Wasn’t Smart Enough To Date You When I Was That Age

  1. AWESOME explanation…. IF ONLY all women would open up to the possibilities of meeting someone older. They MIGHT even meet the perfect man for them. I am a 47 yo male that has dated from 30 to 50 and I still find those in fear of dating ‘out of their range’ women. Seriously, what difference does it make???

    Liked by 1 person

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