So, I had an incredibly fucked-up childhood in a toxic abusive environment and never really learned how to people.
When I was younger I was... abrasive, let's say. Or possibly just an insufferable prick. I would argue with people on the internet a lot and generate a lot of conflict - not from a desire to troll (as many assumed), I was just raised in a test-to-destruction environment where loud table-slapping debate was just how you learned things - kind of cage-match debugging sessions kind of thing.
This didn't make me many friends, understandably.
Anyway, decades passed and I learned to mellow out a bit, to go along to get along, and to develop some soft skills like y'know, tact, and... compassion for people's emotional investment in their intellectual position, if that has a name.
Well and good, the people I talk to don't generally want to strangle me, chalk it up as a win.
But increasingly of late I've been hearing disparaging talk of 'people pleasers', which as best I can tell seems to refer to people who do all the things I was yelled for not doing half my life: going along to get along, valuing other people's needs and emotional sore spots, taking a cooperative, defensive-driving kind of approach to social ineraction - and I am confuse.
I lack a proper framework to parse this all intuitively; I had to build my social skillset manually by trial and error, and things obvious to others remain somewhat mysterious to me.
I'm not actually ASD (just ADHD), but my lack-of-intuitive-grasp on certain things presents a similar profile. Can someone give me a longhand explanation of the border between not-an-asshole and people-pleasing?
Depends a lot on context.
I'm also a "self made social skills person", although I can't claim the same background or difficulty level as yours. But I am clearly a weirdo who can't grasp half the unspoken social conventions, they require a lot of analysis on my part, so I get you.
"People pleaser" isn't always a bad thing. You can tell by who is saying it and how, if they are making it sound like a selling point then it is. It can mean it's someone helpful and charismatic.
If it's used negatively it means a human doormat or bootlicker although without the loyalty to a person/group you'd expect from a bootlicker. Unlike the doormat, which is passive, the people pleaser will actively go out of their way to give you what you want. This is the person that wants to bring you a cup of coffee you never asked for, the person who will never disagree with anyone, the first one to raise their hand when there are errands to get through, etc.
Since they are willing to set aside their own wants to do what others want, they can be seen as lacking personal ambition and independence, or as someone who can't be trusted since they are easily swayed.