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An event or occurrence that is both endearing as well as painfully irritating all at the same time
Listening to people talk endlessly about how cute their kids are is very endearritating.
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Adjective: Adorably annoying; aggravating, but cute.
As an adverb: endearingly.
"My dog is SO endearritating when he tries to shove his head under my hand while I'm trying to write. I mean, it's so frustrating but it's hard to scold him for doing something so sweet."