Season 3 Wine Downs

Something Insecure knows how to do is ignite conversation across the social sphere. As the third season of the hit comedy got underway, HBO wanted to give fans more of what they love: insight into the mind of creative powerhouse Issa Rae. This thinking — paired with a desire to lean into the buzzworthy topics each episode presents — inspired a fresh approach to behind-the-scenes video: the Insecure Wine Down. Taking a note from Rae’s own practice of “wine-ing down” with her closest friends, Season 3 revamped the concept to feature both Issa Rae and showrunner Prentice Penny as poolside hosts of the weekly, episodic series. Accompanied by guests from the cast, sangria and bright sunshine, the Wine Downs focused on the key themes and personal experiences that informed the episode’s creation and performance. The organic conversation led to candid commentary and insights into the personal mishaps that informed some of the characters’ “questionable-like” decisions.

Each piece had a social-first teaser, where the cast and hosts played “truth or dare,” with questions that related to the show, driving buzz and promoting the longer videos. This fun, relaxed take on behind-the-scenes content became staple viewing for Insecure viewers, who looked forward to new installments following each new episode of Season 3.

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S3 Ep 1: Better-Like

Creator and star Issa Rae, showrunner Prentice Penny and actor Yvonne Orji (Molly) discuss their characters' boundaries and baes over a cold glass of bubbly. See them break down the Season 3 premiere.

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S3 Ep 2: Familiar-Like

Creator and star Issa Rae and showrunner Prentice Penny wine down and discuss why they chose to focus on Daniel's story.

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S3 Ep 3: Backwards-Like

Creator and star Issa Rae, showrunner Prentice Penny, and Y’lan Noel (a.k.a. Daniel) dig into Issa and Daniel’s history and break down their relationship in “Backwards-Like.”

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S3 Ep 4: Fresh-Like

Creator and star Issa Rae, showrunner Prentice Penny, and Lisa Joyce (Frieda) discuss We Got Y'all's fundamental issues and Issa's steamy adventure with Lyft Bae: Nathan.

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S3 Ep 5: High-Like

Creator and star Issa Rae, showrunner Prentice Penny and Yvonne Orji (Molly) discuss an unexpected reunion and the girls’ weekend that went awry in “High-Like.” Spoilers follow.

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S3 Ep 6: Ready-Like

Creator and star Issa Rae, showrunner Prentice Penny and writer-actor Natasha Rothwell discuss friendship growing pains.

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S3 Ep 7: Obsessed-Like

Creator and star Issa Rae, showrunner Prentice Penny and Kendrick Sampson (a.k.a ghost-bae a.k.a. Nanceford a.k.a. Nathan) discuss his character's shady behavior and Issa’s over-the-top reaction.

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S3 Ep 8: Ghost-Like

Creator and star Issa Rae, showrunner Prentice Penny and Yvonne Orji (Molly) break down Molly’s ghost-busting move and the way the finale sets up Season 4.