Shortly before COVID hit last March I had decided to hire an escort to have time with. Now, to clarify this would be considered a higher tier one, meaning more money, that also goes to socials, parties, etc. and wasn't just some cracked out meth head that basically stays at a hotel having one guy after another.
Anyway, this was something that I had considered going through with for a while, as for a very long time I was having issues with my dating life. Through 2017, 2018, and 2019 I was just having nothing but horrendous experiences with women (dating, approaches, numbers,etc.). I was getting women to approach me or ask me out, just to get flaked on. I was getting no results with dating apps or sites. I was forcing myself to approach women that I often felt little to no attraction to, as "practice", and they would just awkwardly stare at me. This was getting to the point where I felt my mental health was starting to legitimately suffer and I noticed I was feeling tons of anger and anxiety. I've already posted this a million times on here but the repetitive thoughts going on in my mind were "I'm 6'4", go to the gym regularly blah blah blah and yet I can't even land a date with a 3?". I was at a stage where I was considering just full blown giving up, as the quality of my overall mental health and well being was not worth compromising. However, during this time I had also started posting on this forum, which made me realize that the issues I had were far more prevalent throughout men of the general population than I had realized at the time.
February of 2020 I had contacted this escort that I had found through tons of research and searching online. We texted back and forth a lot and I explained what I was looking for, etc. We met at a local coffee shop for half and hour, it was part of her screening process and it allowed me to see if it would be a good fit for me or if I'd bail. She actually came across as very normal and interacting with her was much more enjoyable than all of these women I had been approaching despite the fact I wasn't even attracted to half of them. A couple weeks later we met at an incall location that she hosted, it was a small guest house that was in a neighborhood near the downtown area of my city, lots of apartment complex around, etc. Without getting into details, I basically just spent time talking with her, making out and I had a sexual finish. After that I had considered going back for more but I refrained from doing so, as while I did enjoy it I also was aware that this was not a habit to develop. I do remember afterwards that I felt a surge of confidence and that I was approaching women pretty readily afterwards and seemed to have better interactions, but shortly COVID hit and everything was closed down.
Since COVID hit I've had next to no interactions with the opposite sex and I feel that I need to have a confidence booster. For a couple months I was considering meeting up again with this same woman but I hesitated until more recently where I decided to follow through with it and scheduled something later this week. Can something like this be of benefit or is this potentially a bad habit that could develop that could stunt me in some ways in regards to dating? I have the power to be able to call this off and it's something that I've been debating internally, weighing the pros and cons, etc.
I also have behaviors related to experiencing emotions in regards to getting hooked on different things, though I have enough awareness to be able to cut them off early. I really enjoy poker and have experienced and resisted the feelings of enjoying this thrill regularly, though every so often I allow myself to go to the casino to play in tournaments. I also have had similar experiences with partying, investments, etc.