A bit of context first. A little over 6 years ago I ended my one and only relationship which had lasted the previous 22 years. In essence, we grew up together. Learning about life while at the same time slowly exploring our sexuality. As things go, the fire died out to the point that she starfished and I stopped initiating when I felt the desire from her disappear. This lasted for the last 5 years of our marriage before I accepted that the days of old would never return.

Since my divorce, I have tried to find my own pleasure once more, but having experienced my previous partner go from the sex drive of a teenager/early 20's to nothing at all, I have some hangups about my own ability to perform. Was it me? Did I just lack the ability to please her? These are only a small number of my inner worries.

Needless to say, even though I can write the most detailed and imaginative stories for random women here on Reddit, I find myself completely skittish and lacking in confidence out in the real world. I have spent the last 6 years in dating apps, been on 3 first dates and managed to make it to the first kiss with one of the three. It didn't survive though. The whole bar scene/hook-up culture/one-night stand thing is a no go for me as I find I am the quiet, reserved type and such situations require way too much in the way of outward "presentation" to make me even the slightest bit comfortable. The thought of a newbie night at a lifestyle club has crossed my mind, but feels monstrously daunting.

My self-image has been suffering and as a result I do not see myself as a potentially attractive person to anyone that my personal preference has me attracted to. Could it be that I am still hung up on her? Or that, despite my imagination and desires, I fear failing to perform with someone new? I have thought about paying for such services but I live in Canada where it is illegal to pay for those things. The fear of being set up and charged on top of the other worries is just too much. Hell, I tried strip clubs just to feel myself get hard in person with another woman, but failed. Paying for attention was just as bad as having the past partner just lay there, giving in out of some warped view of obligation.

So here I am, desiring physical connection with a woman that I find appealing, along with the mental connection that will get me out of my head. But, despite wanting these things, being so emotionally crippled, I have failed to meet a woman to fulfill this role or even get out of my own head long enough to see the possibility of such a woman existing for me ever again.

Has anyone experienced this? How did you get past it? Any advice from the opposite side that might aid in finding someone to let in? Any and all input is welcome.