When Should I Actually Have Sex With Someone?

[WDK]

I got out of a relationship in late 2019. I went on lots of dates in the last 18 months and talked to several hundred women and I screened all of them for some basic criteria to establish a good fit. I had never done this before, and i did it so I wouldn't waste my time or the woman's. After all those dates, I found one girl that I liked a lot that met all the non-negotiables. For several reasons, part being a values difference, part being she was too busy to pursue anything serious (MBA plus fulltime job), I am now single.

I've decided I'd like to focus on my life purpose and spend some time each week going out and talking to women for the pure purpose of honing my skills. I did this last night and got 2 numbers without focusing on the outcome of actually doing that. I focused on eye contact and having fun interacting with them (a very difficult thing for me sometimes).

I have tried any woman that wanted me, that didn't end well. I also tried getting the "right woman" which didn't actually end up working long term even though I spent 18 months finding one I really liked and thought would work out. Also, part of me realizes that since I'm working on my life purpose if I don't have any outlet for my sexuality at all, it may lead to worse habits. I have not had sex for as long as 3 or 4 months because I didn't find a good match even though I was going on dates every week. I could do that again if necessary.

If I am trying to get better with women through practicing the core skills, should I have sex with women that do not fit my basic criteria (Them not having kids, politically moderate or non-polarized, and non religious or at least does not go to a traditional church) ? Or would that be detrimental to them and myself by getting caught up in a distraction?

Edited October 3, 2021 by WDK
Edited for brevity

[Harlen Kelly]

9 hours ago, WDK said:

I also tried getting the "right woman"

There is no ''right woman'', there are right womEn. There are hundreds of thousands of women who would fit the psychological, physical and emotional criteria you are looking for, so get the childish idea of ''the one'' out of your brain, is cancer. 

I would suggest you to have fun for a couple of months and be a little flexible with your criteria for a sex partner, after exhausting for desire for sexual variety and doing some soul searching (ie working on your life purpose as you previously mentioned), aim for a monogamous relationship with a high-quality chick if that's what you want. 

[WDK]

Thank you I appreciate the advice!