Issa Endures (and Worsens) A Series of Terrible Dates in ‘Insecure’ Season 2 Trailer


Issa Rae has shared the trailer for the second season of Insecure, and it picks up where the last left off — which is to say, Issa is now immersed in the abyss of dating, following (spoiler) the explosive deterioration of her relationship with Lawrence (Jay Ellis) that made up a good part of the first season’s second half.

The trailer begins with Issa once again engaging in a confidence-building/deflating monologue with a mirror, then plunges into a montage of bad and/or awkward dates. She tells her bestie Molly (Yvonne Orji) that “of course [she] wants Lawrence back” — which leads to a perhaps ill-planned sexting whim — as we see him, in the meantime, continue his status-shifting antics as he exercises and further embodies the ideals success Issa resented him for lacking at the beginning of Season 1. (But seemingly, he’s still not over her, either.) Meanwhile, Molly is processing the new knowledge that her white male coworker is earning more money than her.

Season 2 begins its eight-episode run on HBO on July 23. Watch the trailer: