Producer Masego's brother's tailor trouble with his new school pants has us all flashing back to our high school fashion fails.

From awkward first crushes to questionable fashion choices, we're diving deep into the cringeworthy, hilarious, and sometimes heartbreaking world of high school "cool." We explore the lengths we went to (and maybe still go to) for social acceptance, dissect the ever-shifting definition of "cool," & share our own tales of teenage triumphs and epic fails.