: Reviewers on Wherever-I-Look and Decider highlight the realistic portrayal of 20-something dating and the struggle between staying in a comfortable relationship versus returning to the brutal single life.

: Issa spends the episode avoiding Lawrence to delay a conversation about their stagnant relationship. A tense run-in at a Rite Aid highlights Lawrence's obliviousness to the actual problems between them.

: At her job at "We Got Y'all," Issa struggles to propose effective ideas for middle school students, feeling increasingly alienated by her culturally out-of-touch coworkers.

: Directed by Cecile Emeke and written by Issa Rae , this episode originally aired on October 16, 2016. Insecure: Season 1/ Episode 2 "Messy As Fuck" - Overview

: To bounce back from a dating drought, Molly treats herself to a "Molly Maintenance Day". She explores various dating apps like Tinder, Hinge, and OKCupid before bumping into Jared, who remembers her as the girl from the "Broken Pussy" open mic.

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