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I’m currently in the classic older man and younger woman relationship. I’m 50 years old, Nancy is 30, and we are both divorced. I was not looking for anyone when Nancy came into my life. She is beautiful and sweet, and I absolutely adore her.

I could think of a million reasons why it doesn’t make sense to have a relationship with a younger woman. But she doesn’t feel that way at all. So why am I writing? At this juncture in my life, I simply can’t see this relationship in the long term.

I have told Nancy not to waste time with someone like me; I have far less life to live than she does. She insists I have plenty of time left, though I cannot see where this could possibly go and be good for both of us. Am I simply sounding like some insecure, middle-aged idiot, or should I enjoy what we have and see where it leads?


Simon, if you know something in your own heart that prevents this, or if there is an issue you haven’t resolved, such as having children, that’s one thing. But if it’s simply the idea of the years, the years don’t matter.

To suggest the difference in age is the problem implies being close in age would guarantee success. But that is not true. Many couples in the United States divorce, and most of them are close in age.

It is love that is the center of everything, not the number of years since your birth. It is love which creates alignment and balance between two people. What matters is that you love each other and belong together. In addition, there is no guarantee Nancy will outlive you.

Being an insecure, middle-aged idiot is no fun, so we suggest you enjoy what you have and see where it leads.

Wayne & Tamara

Free Will

My story is like most others. All the signs were there, but for some reason, I wanted to believe the lies.

My former boyfriend met his ex-wife behind my back. I also suspected an affair with his boss. That thought nagged me. So one night when he was away, I looked up her address and drove there. Lo-and-behold! His car was parked in her driveway at four in the morning. He said he left it there for convenience while he went out with friends for the night.

I guess the question you get most is why. But I don’t want to know why he did these things, but why did I stay with someone who would cheat on me? Why would I want to believe the lies so much I went against my own logic?


Tiffany, if you are less than 70 years old, you have been raised all your life to believe we can make any relationship work with the right amount of hard work, compromise, and communication. That is what the “experts” claim. It isn’t true.

The end result of believing every relationship can be worked on and worked through is there aren’t any warning signs anymore. It is like saying since medical people can effectively treat burns, you no longer need to remove your hand from a hot stove.

You wanted a loving, monogamous relationship. That is who you are. He wanted to play the field and be intimate with whomever he wanted. That is who he is. Neither of you had the ability or the right to change the other. You tried to apply what you desired in a relationship, and what the “experts” claim is possible, to the man you had. It didn’t work.

At the time, you couldn’t see there could be someone else for you who would be loving and monogamous. That is where you needed to go because no one has the power to change the behavior of another.

Wayne & Tamara

Wayne & Tamara are the authors of The Young Woman’s Guide to Older Men, The Friendship Solution, and Cheating in a Nutshell—available from Amazon, Apple, and booksellers everywhere.

Photo Credit: Aranprime


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