Also I'm still doodling away, although doodles don't really make it to MLPG so I mgith as well give the link out - this doodle was done for April fools: https://twitter.com/UCNSFW/status/1377745227604185096
I just want to go into a bit of detail here and say that, despite how ridculously off-tone this comic doodle is, it's basically certain the Anon-PB relationship would play off eachother like this.
Yes, I envision Anon AND PB have a very solid Anonymous relationship, simply because PB is the closest thing Monstro has to an actual 4chan user, which is Anonymous's entire society and the culture he was born into.
It's not NICE, but it IS something that gives them a nice relationship arc, even if in my head I know Anon's personal issues would clash with PB's personal values - but, well, that's just sort of what a relationship IS, really. They basically work to bring eachother's best out, and it's hard bloody work sometimes, but by god is the result worth it: people probably wouldn't even recognise PB if she didn't have the uncurable habit of being a cheeky little shit, And Anon might actually not feel like he doesn't belong in any sort of reality, with a strong incling of staying in this reality that involves him and PB having an Understanding.