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 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.

  • Savta Pur­ple

    It can be tough to date an older man but there are a lot of benefits.

  • Trish Kendall

    Older men have a deeper appre­ci­a­tion for a younger woman and you are likely to be told how beau­ti­ful you are, how much you are loved and appre­ci­ated every­day. That was my experience.

  • Amy Michelle Mosier

    I mar­ried an older gen­tle­man, which is great, but this arti­cle is about an already mar­ried man that owns a jet and lives in another state. I think this story applies to just a few trashy Hol­ly­wood types, not real people.

  • Sam Fur­self

    There goes these bunch of money hun­gry mis­tresses defend­ing their sin­ful ways.. tsk tsk! You aught to he ashamed of yourselves.

    • Ted Heiss­ner

      And yet they sup­ply some­thing their com­pan­ions need. Their sugar dad­dies wouldn’t be with them if their wives sup­plied what they need emotionally.