Second Act Dating: Don’t Jump In Too Quickly

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I thought that finally, at age 50, I had found the one.  His name was Gregory.  He checked almost every box in the mental list I had constructed and carried around in my head once I began dating after my divorce. Kind. Intelligent. Funny. Honest. Handsome. Faithful. Financially stable. So why wasn’t I happy?

The first two months were wonderful. I was in a whirlwind of intense passion and thought that maybe I had found my true soulmate.  One of the things I loved most about Gregory was his expressiveness. He had no qualms about speaking of the future. I was ready, at his suggestion, to move in the following month. Yes, it was soon, maybe too soon for such things, but dating at 50 brings an awareness of the scarcity of time and can, for better or worse, cut through much of the holding back one does at a younger age.

I told myself not to be afraid, that if have the good fortune to meet such an amazing man who seemed to be everything I had ever wanted, I should go boldly forward without fear.  Two months into the relationship, just as I was arranging to forward my mail and give the neighbor the key to my apartment, things changed.  He changed.  The first thing I noticed was that that the beautiful, sincere words that made my heart soar suddenly and inexplicably disappeared.  Where once he had spoken eloquently of an intense longing for me, he began to focus on things of a much more mundane nature; ie, how many bags of mulch he had put into the front flower beds. In the beginning he texted me love poems and links to love songs, now he was sending pictures of his dinner.  It was as if the passion and intensity had abruptly been extinguished.

I thought it might be a phase, one of the typical ups and downs relationships experience.  I told myself that the intensity at the beginning is not something that can be sustained long-term.  Yet this change is typically a gradual dissipation, which is replaced over time with something more substantial and meaningful, though not nearly as exciting.  However, this change in Gregory wasn’t gradual or evolving; it occurred almost overnight.  I had no idea what had happened.

I didn’t realize it at the time, but the catalyst for this change was something that at first seemed to have nothing at all to do with us. Gregory’s 33 year-old daughter and her 22 year-old boyfriend moved into one of his upstairs guest rooms while I was there.  Both were unemployed and showed no interest in finding jobs.  They spent their days smoking cigarettes and weed, playing video games, lounging around, and no doubt having plenty of sex.  This arrangement was supposed to be temporary, but it soon turned into weeks and months.  As time passed, I found myself deeply longing for the man who had so swept me off of my feet.  His demeanor and attitude changed drastically. I thought it would be best to simply end the relationship.  However, I remained steadfast and supportive, believing that his houseguests would soon move on so we could eventually turn our attention back to our beautifully blossoming romance.

That never happened.  Instead, I learned that this wonderful man was enmeshed in an unhealthy, codependent relationship. While Gregory, age 66, got up daily and went to work as an attorney, the daughter slept in and loafed around the house.  The sink was full of dirty dishes. No chores were completed.  Resentment began to build in him, yet he was unwilling to set any firm rules.  The stress bled over into our relationship. Although he was never harsh or inconsiderate, he wasn’t fully present, vacillating between being distracted or self-absorbed.

His daughter talked of grand plans to find work in Pennsylvania, but those plans never materialized.  As I watched Gregory struggle, I began to see his utter feeling of helplessness to change the situation.  He knew that what was happening wasn’t right, but he was so conflict-averse that he couldn’t bring himself to confront them. I learned from other family members that he had rescued the daughter her entire adult life.  He felt guilty about his divorce, I surmised, and he assuaged his guilt by bailing her out of disaster after disaster. As intelligent and intellectually sharp as Gregory was, he couldn’t see how the situation was directly affecting our relationship.

At the age of 50, I chose to date older men for many reasons.  Older men tend to have grown children who live their own lives. Gregory was a great guy.  He checked so many boxes so I gave it time. I had gentle talks with him about what might be most helpful, but it never seemed to sink in.  He would agree that things needed to change, but would never follow through with any action. His home situation ran counter to everything I believed in and tried to practice in my daily life. Our relationship took a back seat to his codependence.  It finally spelled the end for us.

I learned something very valuable from this experience.  Even though there is an aspect of acceleration in dating over 50, it’s important not to let that sense of urgency override prudence and a healthy dose of optimistic caution.  I thought Gregory was the one.  He wasn’t.  He was, however, a great teacher.  He made me aware of the value of time and how not to let those first few fiery months fuel major life decisions.  My heart is heavy when I think of how quickly our passion dissipated into a lukewarm kind of complacency.  Yet I am also grateful for the lesson it taught me.

I hope that Gregory also gained something from our time together.  I don’t know if he still has two houseguests, but if he does, I hope that he finds a way out of that complicated emotional maze and can do the difficult task of detaching from his daughter with love.




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