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Podcast - The New Dirty John


"DL" ASKS:


I’m a 52 year old male and have been single most of my life. My last relationship ended ten years ago. I have had zero luck meeting anyone on dating apps since I hit 50. I do a little better online, but it never goes anywhere. Career wise, I have a job that requires extensive travel and frequent moves. I’ve finally come to terms with the fact that I will always be single. I have a friend, M, who is 59. We met each other thirty years ago through work. She lives 500 miles away from where I now live. Back then, we went on a date. However, I was interested in dating younger women and also interested in starting a family (which never happened). So it never went anywhere, but we have stayed in touch over the years as distant friends. Like me, she has also been single for a long time since her thirties (and childless).


Recently, I’ve been thinking about her with more interest. The last time we met, she looked attractive to me and her body is still amazing. I told her this, which was very well received. We have been emailing and texting very frequently ever since. The communication has also assumed sexual innuendo. We have agreed to meet up for a weekend soon, in a city she has always wanted to visit. I paid for her trip through my loyalty card points. I will be flying in as well. I did make it clear that I have friends I can stay with while we are in town. I didn’t want her to think that I presume we will be sharing the same hotel room.


Obviously, I would like to spend our nights together and also have sex. I have not had sex since my last relationship (yes, that’s ten years) and she has implied that she has not had sex for a much longer time than that. I plan to just have a fun weekend, and if she invites me back to her room, great! If not, I’m okay with that. My question is if we do sleep together, it’s obvious that this will not be a relationship, unless it is a long distance one. My job will never let me settle down, and I know that is a choice I made long ago that hindered relationships. I don’t want to hurt her. If I was really that selfless, then sex should not be on my mind, but let me be honest: I’m aching to have sex with her.


Looking at her is what changed my outlook to date an “age appropriate” woman and I find her much more sexually appealing now than younger women. She is comfortable in her body, and in her current lifestyle and routine. I am assuming that at our ages, we should just go for what we want. I presume she knows our life paths are different, but what it she expects more after sex? Your suggestions will be helpful, because there is so little out there for singles at this stage of life.


Hear our answer in this week's podcast.