I've only ever heard the term used to make fun of old people and corporations trying to sound cool. I've never heard someone use it sincerely and I don't think I've even heard someone actually use it in an attempt to sound cool. I'm quite certain I've only heard the word ironically and I really can't imagine someone using it sincerely.
Did anyone actually ever say "On fleek"?
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Some_Fellow_411
It’s actually from AAVE (African American Vernacular English) so it can sound really awkward when people say it to sound.. hip/cool, because it’s just not from their dialect. Also half the time they don’t quite realize why they’re emulating American Black people or even who they’re emulating. Very strange stuff imo
micika
Some people I know use it unironically, and theyre not weird or something, they belong to the more popular bunch