The Biggest Fear I Had to Face About Dating an Older Man


I was dating an older married man, which is a relationship that comes with its own set of concerns.

I was dating an older married man, which is a relationship that comes with its own set of concerns. I was worried that if anything happened to him in the way of a health issue or an accident, I would be the last to know. Would the phone just stop ringing one day? Would I need to check the newspaper to see if he was still alive and healthy? We lived in different states, so it wasn’t as if my local news channels would broadcast any information concerning my boyfriend, the Stetson man. These were the thoughts that often raced through my mind at the start of our relationship. My friends were aware of the Stetson man’s existence very early into the relationship; for obvious reasons, most of his friends and family were not aware of my presence. I was in contact with his attorney friend, who I got to know because he often traveled with us. Really, he was my only outside connection to my boyfriend, and we became very close. The attorney was closer to my age, and so we had more in common. I enjoyed him being around, like when we would have pop culture trivia contests, a topic that the Stetson man knows nothing about. That first fall together, I was continually worried about my boyfriend flying in his private airplane. At one point, I sat his attorney friend down and voiced my concerns. He chuckled, and then he reminded me that my boyfriend drove a V12-engine sports car. The attorney thought that the Stetson man was safer in the air with a pilot at the controls than he was on the roads, speeding the way he normally did. I had often heard the running total of speeding tickets he had wormed his way out of—the last count was over 15. But my worrying did not subside, and late that fall, my concern was at its peak. A foreboding feeling had come over me, and I could not help but think it had to do with my boyfriend. He was older—much older—he flew many times a week, he drove recklessly, and he was under a tremendous amount of stress. My uneasy feeling had to be about him. Who else could it be? Again, I brought up my concerns to the attorney, but instead of answering me, he ignored what I’d said and asked if I wanted to attend an upcoming horse race with him; he was in the process of obtaining tickets and needed a head count. When he mentioned the date, I already knew the Stetson man had other plans that weekend: his wedding anniversary. And then I realized that the attorney had been tasked with keeping me occupied during the anniversary weekend. The plan was to take a private plane to the race. The Stetson man’s plane was not an option because he and his family would be using it as part of the anniversary festivities. When that weekend finally arrived, I was at home alone, with the foreboding feeling in full force. After the race, I had flown on a commercial flight back to the Stetson man’s state on the evening of his anniversary, and I was waiting for him the next morning when he phoned and said that he was on his way over to see me. As soon as he walked into my hotel room, I knew something was not right. It was then that he told me that the plane carrying the attorney and his friends had crashed on their return from the race. There were no survivors. I lost a dear friend that day, as well as a connection to my boyfriend. As time unfolded, I discovered how drastically the airplane crash changed the dynamics of our relationship. - See more at:


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