[quote=@Poi]Tl;dr Friend is doing a 1x1 with me and often annoys me with instant notifications or multiple notifications in the same time frame.
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I have been in this boat, though mine was in Skype rather than Discord as it was a few years ago. My partner would pester me [i]every day[/i] with the question of essentially “Where’s the post?” as if I was beholden to him. This was not a pace I was comfortable with, so I started acting spiteful. My method probably would not be beneficial to your situation, but at some point you are going to have to draw a line and say effectively that enough is enough and you need to not do this and they need to [i]understand[/i] that.