Dating Insecurities

I have said before that I believe most things happen for a reason or to get us where we are supposed to be in our life. This might be a juvenile ideology but it has gotten me through some bad times and many of the wrong turns I have made. It also seems to have worked for me since I am at the most perfect place I could imagine. Married to a man I never thought I would be lucky enough to have. This does not mean however that I never sit back and wonder about my psyche or how I could have behaved or acted the way I did in the past. There is always something to learn from our past behaviors or actions.


I was having a conversation with Aaron a few nights ago and I told him that when I was single it was easier for me to go on a sex date than a real date. I have been reflecting on this the past few days because I think it was kind of a sad statement I was making about myself. I hope I am not the only person who has ever felt this way. If so I am pretty fucked up.


I find it hard to believe that I could bare my body to someone easier than I could bare my personality or who I was to someone. I know growing up I never felt good about my personality or my looks due to the great parenting I had. Even into my mid 20’s this poor self image was following me. I remember remarking to someone that I always felt thought my zipper was down because people were always looking at me. They told me not to be stupid people were looking at me because I was handsome. I honestly never even gave a thought to the possibility I might be good looking until this point. I imagine I went home looked in the mirror at myself for a few hours and still did not believe I was good looking. In addition I had played sports in high school and continued in college and worked out and ran, but still never even considered I had a good body. I guess I tried not to think of me. As for my personality even though people liked me and I was myself I never quite had faith in myself or knew who myself was. It was probably not until my 40’s that I began to like myself and know my true self.


Pictures of Mike in his 20's.

So go figure here I am in my 40’s and 50’s not ugly with a fairly good personality, good looking, good body but too insecure to date, well not to date but to ask someone out. If I had been asked I most likely would have said yes in a hot second. When I asked friends why they thought I wasn’t asked out they said the impression they got was that people were afraid of me or they thought I was unattainable. I thought that was a joke.


I think it was always the fear of rejection that kept me from asking someone out. Despite knowing I was a so-called, “good catch,” in the back of my head I kept hearing that voice saying I was not good enough. It’s odd when I think back almost all of my relationships have started out in bed. Maybe that is why most of them did not work out. I never took the time to “really,” get to know them first. Unfortunately for me one good night in bed was enough when it never should have been.


Picture of Mike at 40 and 55.

I find it so odd though that I had no qualms about having sex with someone I did not know and did not feel like I was exposing myself to getting hurt Probably at this point I had more confidence in my body as it was something tangible that could be measured unlike my personality. Aren’t we supposed to be at our most vulnerable when we are having sex with someone? I was actually more vulnerable and nervous sitting in a bar or restaurant waiting for a date than waiting for a sex date to arrive at my house or maybe the thought of cumming was stronger than my nervousness.

I was always so surprised at how easy it was for me to talk to a sex date after having sex. Maybe as I said before it was because I had exposed so much of myself to them already. After cumming and really letting go I would feel completely free in a sense. That feeling of compete relief and being totally spent I suppose allowed me to lower my guard. I was always pretty particular about my sex dates and did a fairly good job of sussing them out in our texts or over the phone. I do not think that harbouring a secret fantasy that my sex date and I would begin dating did me any good. A better one would have been to just have imagined all the different ways he or I were going to pump and dump the whole night


Going on a date had its own set of pressures that I did not enjoy, First and foremost I was going to be wondering if the person was going to like me. See, right there that’s a good indication I was a little fucked up I should have been wondering if I was going to like them. Then all during the date I would be mind fucking myself I would wonder who should pick up the bill, was it too soon to go, should I kiss him goodnight or shake hands, should I say I had a good time? Almost worse than not liking the person was when they liked you, and said they wanted to see you again and you had to say no or you could feel bad and lie and say yes and cancel at the last minute. All of these things that I would have to address would be going in circles in my mind. For someone who did not enjoy conflict this was not fun, Strange because at work I always thrived on conflict.


I remember one time I did in fact ask someone out I met online. I was so excited. He seemed to be everything I could want in someone. At the last minute he told me he did not go out with smokers, which I am, anyway I said that was not a problem. When I told my friends about this they asked what I was going to do. I said if he is good as he sounds and looked on his profile I will never smoke again. Anyway I met the man at the Ritz across the street from my house for drinks. When we were leaving he said he was going to catch the subway. I said I had to go that way and would go with him. As soon as I dropped him at the subway I went running to the nearest shop to buy some smokes. To say the least he was nothing that he said he was. I think that was my last date.


Another funny incident just came to mind. I would usually always host my sex dates but for some reason I can’t remember why, I ended up at some guys house. Well it was about 3:00 AM and I was sneaking out of his apartment and all of a sudden I hear him yelling see ya later quick draw.

(Guess I came a little too quickly.)


Not hanging out with a gay crowd I am not even sure if we do date anymore. I was adverse to even joining an online dating service. Again a poor self image thinking what was wrong with me that I needed a dating service. What was wrong with being honest and just saying I wanted a relationship and did not meet many single gay guys. I do believe dating sites are a bit contrived but it seems just about everybody uses them. Another time I will talk about this, but I think it is sad that it seems so difficult to meet people in a social situation these days because people are so caught up in their lives.


I do think my insecurities made me lose out on a lot. Dating ought to be fun. I wish I had believed more in myself as I really do enjoy meeting people all different kinds of people. I would even venture to say I am a people person. Even if the date stunk you could always learn more about what you did want or didn’t want in a person and who knows you might just fall in love.


Age gap relationship couple, Aaron and Mike on their wedding day.