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Dating Older or Older Dating!!

Updated: Feb 26


I really do not know how to start this, but lately, I have been going through the motions and really thinking through what the implications of dating someone older are. I mean the funny thing is if you are twenty-five, and he is forty-five the age gap does not seem to be significant. When you hit your thirties, and he is over sixty you start to wonder if this is indeed possible.


I recently met an older gentleman lets call him Mr.X. Well, Mr.X was well dressed and refined with just enough breeding. Came from good stock just as I like them and boy oh boy was he a gentleman indeed. In fact, Mr.X for an American could be compared to an Englishman any day. I was excited about this date and decided to put on something casual for the date. I had to think through it all. Something not too sexy, perhaps, not too young looking,  a bit on the sophisticated side I said to myself. My date was supposed to pick me up, and so he did.

I can never forget getting into the car and the first thing I noticed is how much older he looked than the night when we first met. He was a handsome gentleman probably in his day, a charmer considering he had been married three times before as he would later reveal to me.


However, I could not but help notice the liver spots on his hands. My eye caught sight of them, and I was like thinking at the back of my head. Boy oh boy, this is an old man I am dealing with. Then I thought about his charm and told myself to stop being so superficial.

On the way to the restaurant, he had to go to the bathroom and while at the restaurant he had to go at least another four times. Considering we where there for about three and a half hours this was I guess usual for a man his age or was I overthinking it? That said the date went fine. His stature though frail was very pleasant and he was an absolutely great delight. He dropped me home, and that was that I never saw him again.


Now, this is where the story gets a bit complicated. I never heard from him again. Though at the date he was so excited and could not even believe his luck as he had told his friends we had in common. But when he found out how young I was and that I was much younger, I think that perhaps put him off as he said he did not realize how young I was. I mean being in your thirties is really not that young.


Anyway brings me to my topic of today. Dating older is a matter of choice, but especially for women dating older men, there is a lot to think about. A lot of these guys are set in their ways and coming into their lives means fitting into a role, a space that they have made for that particular person. Your enthusiasm for life maybe just a bit more spunky than theirs, and you may want to tone it down. Though here in Los Angeles the average sixty years old will behave as if he is thirty-five and wants to have a good time and stay single.


Dating older is really a production, and you better be ready for it. Most older men really do have a routine. You play the younger woman, and you have to put up and cater to their life. Also, they are just not as virile and my guy was a bit on the scrawny side. I did not even want to imagine him with his clothes off. He would have probably provided me with a dream life, the type women read of in magazines with an allowance for designing our dream home and money to spend on as many Chanel purses as one could need. However, the spark of youth was missing you know someone that you could have fun and toss around with. I am not saying every 68-year-old man is like he is. But if you know where I am coming from you get my drift.


I think you should date any age but for the right reasons and I also believe in falling truly profoundly and passionately in love with someone. They also have to match you physically though I don’t really mind either way. I did feel like I was going to dinner with an old man who was frail. I felt like Wonder Woman next to him, strong tall, beautiful and powerful. Maybe it was a bit too much for him. Or perhaps he was a bit too frail…….lol

Dating an older man can definitely be a piece of work. You really need to know what you are doing and what the end goal is. Unless of course, you are after his purse strings! Then my advice to you will be to you will to put on all the stops, take no prisoners and grab yourself a Sugar Daddy!!!

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