A reader actually asked the above question (in more or less those words) in view of my recent friendship with L, an active WL. Since real life will likely put a screeching halt to any kind of blogging for a few weeks (or at least significantly reduce it), I will answer this question now.
I'm assuming that the author refers to making friends with a WL that I have seen as a client in an active sense, rather than (to some extent) as dictated by circumstances, like how Erin and I wound up working for the same company. The answer(s) to the questions are as follows: "Almost certainly no" (as in 99.999999999999%) for any other WL that I see/will see and "Yes, I would give it a try again if the clock were wound back and based on what I know about L now" for her.
Let's start with the first answer. The reason why I didn't say "Absolutely not" even though my answer is pretty close is that I think outright denials about future possibilities are generally intellectually dishonest. It's easy to sound like a Hero of Clarity ahead of the time and ahead of all the head-spinning. However, I think I will almost certainly never pursue another friendship with a WL for the following reasons.
For those familiar with the Myers-Brigg personality test/types (Google it if you want to understand more), I am an "ISTP". In simple terms I am primarily introverted (i.e. preferring internalised analysis and thinking and comfortable in my own company/isolation), prefer to rely on concrete data/analysis in discerning the world, prefer thinking things through based on logic and reason, as opposed to acting based on an internal "feeling"/barometer, yet I am also spontaneous, flexible and open-ended but with a healthy desire for order.
In short, for someone who's not desperate for friends/company and with my kind of mentality and knowledge of the rules of the game (i.e. money for company and not emotions), there's little within me that pushes myself towards wanting such a friendship generally. More importantly, my extreme inner-drive that comes through in terms of upholding fundamental personal values such as not wanting to hurt another person, wanting to do my best with the resources available etc, means that relating with me can be rather intense. That coupled with a difficulty in expressing feelings and emotions cogently/succinctly (I frequently wonder if L and others quietly wonder if I am a bit emotionally "slow") can be a recipe for disaster for those who just don't "get" people like me.
And I am indebted to the authors of this website for their description of the typical ISTP's attitude towards sex. I find it especially applicable when it comes to my attitude towards casual encounters:
Sexually, the ISTP approaches intimacy as a physical act rather than an expression of love and affection. They are earthy and sensual beings who enthusiastically experience sex with all five senses. They bring spontaneity, creativity, and enthusiasm into the bedroom, and enjoy new experiences. Since aesthetic beauty has such strong appeal to them, they appreciate the "setting", i.e. bedding, lingerie, cologne, etc.
Yep, whilst my values system absolutely demands that I respect the inherent dignity of every person that I am with, 99% of the time my casual interlocutor is just a "number". No emotions are left behind or expected. Sorry if this offends.....
Then there are the practical considerations as well. With my personality type, I tend to prefer smaller group or 1-on-1 social interactions and not everyone is as keen on this. Then there's the issue of how I and the other person is to explain our friendship to the wider, sceptical world and my own need to respect the fact that I am in a stable relationship. Only those that I am confident about having the emotional stability, insight, and fortitude to understand why we can possibly have a friendship despite how we met and despite my personal relationship background will really get a look in. In short, from my point of view, my friendship with L broke with my usual type and to some extent I can't explain it. Personalities and personal characteristics are not, after all, fixed.
As for why I would choose to try the friendship game with L again if the clock were wound back? I will just let my last posts speak for themselves since I am aware that she occasionally reads this blog and I could be getting corny.
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