Random words
These are words that seem striking to me. Mostly they're just long/obscure.
eleemosynary
susurration
encomium
internecine
vituperative
pulchritude
messlessness
plenitude
palimpsest
grandiloquent
lugubrious
Bad words
learnings
This word is extremely uncomfortable to hear, just say teachings or lessons... From the wiktionary page linked: "from circa 2000 it became a buzzword in business speak, particularly in constructions such as “key learnings” or “apply these learnings”"
orientated
This word sounds clumsy with the extra syllable, I think oriented means the same thing and sounds much more natural
gotten
I don't like most American words/spelling but I can get over them however this one tends to tick me off for some reason. It's weird because I'm okay with forgot and forgotten but not with got and gotten.