Trying to figure out this dating world as a 50+ man is a bit complicated. Especially when you have been off the market and out of the habit for the past 25 years. It is a whole new ball game. But it seems the “Games” are still the same.

Being a man in his prime, I am not about to jump into the cesspool and play games of a kind. I don’t have time for that shit. I would rather focus on things that actually bring joy, meaning, progress, happiness, and mental stability to my life.

Now don’t get me wrong, I do think that dating and a potential relationship can add a lot of those same attributes to my life. It is putting in the effort and time to develop a relationship that seems to be hard.

My one and only interest whom I have spoken about before is proving to be a challenge. When my friends and my family ask me about him, I am honest and I call him my comfortable distraction. A 27 year age difference is a lot and our values, goals, and ambitions are very different. They are sometimes confusing and frustrating.

We both said we are interested to see where this distraction leads. But damn it is proving difficult to even find time to spend together. I would say we got into our first little “tiff” over it. And we have been a bit distant since then.

I do know that I don’t want to be the one putting in all of the work and communication. I did that for 25 years. I know that type of relationship not what I want to do again. it was mentally and physically exhausting.

In my relationship with Kerry, if I didn’t come home and start any type of conversation, he would not speak to me all night. I could be happy. I could be sad. I could have had a hard day at the office. It could have been any number of things. If I didn’t start up the convo, it never happened.

And God for bid I ask him how is day was. I would get yelled at and told, “it is the same as every other day. Why do you keep asking?” I stopped.

I would also have to ask, “Do you love me? Do you love me?” and one day I got yelled at. It was years ago.

He yelled again, “Why do you keep asking me that?”

I never asked again. And Kerry never told me again that he loved me. I am learning now that this took a real toll on my self worth and my self esteem. I feel those emotions now as I move through with time with my current interest. I am very guarded. I ask him when we can spend time together, I get very little, and he has a lot going on so I try to be patient. But then I find out he has time to hang with other friends and I don’t feel I am getting the same courtesy.

I go right back to those feeling of no-self worth, and all the insecurities that go with it. Im too old. I’m too fat. Im not good looking enough. Im not exciting enough. Fuck I don’t know. And then my mood goes downhill and all the self deprecating thoughts come into my head. I spiral a bit.

I don’t want that. My friend Dave said, “Well then, you know what to do.” I should give up. But then he smiles and I don’t want to give up. Im struggling to say the least.

Age is a big thing. He is starting his life and career and I am excitedly anticipating retirement. I want to play! I want to change my life and move in. a different direction. I don’t want to be tied to my house. What the fuck should I do?

UGH.