Insecure's Kendrick Sampson joins Issa Rae and Prentice Penny on Wine Down

Source: Merie W. Wallace/HBO / HBO

Insecure is headed into the season finale this Sunday and there is a lot on the line for season 4. It looks like Issa and Molly are done for good after Molly accidentally-on-purpose sent Issa a shady text that revealed her true ain’t-sh!tness. Issa and Lawrence are back in the sack but will be they be couple again? Issa has to decide how to put Nathan in his proper place now that she’s back with Lawrence. Everything is a f***ing mess.

One of this season’s most powerful moments came last week when Nathan revealed his battle with being bipolar and made Issa feel *this* small when she tried to come at his neck for “ghosting”. Issa (the real one) gives some perspective on why that scene was so important.

“I think that that puts so much in perspective. It goes from a typically millennial dating experience of a man not being able to use his words and then coming back around like ‘we good right?’ To, like, ‘oh he actually had personal mental health issues that he needed to deal with and he needed to take the time to do that. You become more understanding…”

On what would appear to also be the penultimate episode of the after-show companion piece Wine Down, Kendrick “Nathan” Sampson joins Issa and showrunner Prentice Penny to talk about everything that happened on “Lowkey Trying”. The trio also touches on the awkwardness of his lingering feelings for Issa and what might come of that in the finale.