Harlem night(plural being harlem nights) are an unspecified amount of time(could be a minute, hour, day, etc) filled with nothing but complete Ls and despair. The opposite of a harlem night would be a balling night.
by TotallyNotRockman#3581 March 29, 2020
The act of one wearing a Denim Jacket, Jeans (usually of the same color as the jacket) and Light colored Timberland Boots. Ultimately looking like an urban tuxedo, that one may wear when going to their high school prom.
"Did you see Julez Santana in that new Dipset video? Looks like he's ready for that Harlem Prom Night"
by ChuckWellington January 6, 2012