Popsugar Entertainment Kendrick Sampson Insecure: Issa Rae and Kendrick Sampson Season 5 Photos Will Issa and Nathan Get Back Together on Insecure Season 5? See the Promising Set Photos 11 February 2021 by Chanel Vargas View On One Page Photo 1 of 2 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 1 Previous Next Start Slideshow Kendrick SampsonInsecureIssa RaeTV