I can be insufferably insistent at times. If someone says they’ll do X with me, or for me, I will pester them until they do, “playfully” jabbing at them the longer they don’t do whatever they said.

My immediate problem is I have an extremely hard time asking for help, in any context. I think it stems from trust issues. My immediate thought when something needs to be done is “I will do it, or it won’t be done and I will deal with that outcome”, because I think the chances someone else will actually do it when asked, the way I want it done, are pretty low.

Makes you a rock star at work until you break under that expectation you set. Makes for weird relationship dynamics when you help all the time and never ask/expect that it will be reciprocated. It’s just not a great position for fostering healthy interpersonal dynamics in general. I’d argue that it might also sap energy from working towards some things you want done, and are unhappy, deep down, are left undone.

I think there’s even a name for it - helper syndrome or something. It’s a weird “It actually works pretty well, until it doesn’t” position.