Season 4 Wine Downs

Something that Insecure does very well is knowing how to start a conversation on social media. For the past three seasons, creator Issa Rae and showrunner Prentice Penny sat down with a weekly guest to discuss the major events that went down in each episode and the inspiration behind certain storylines over a glass of wine. This season, the Wine Downs explored how the characters in the show evaluated their relationships as they determine who and what comes with them in the next phase of their lives. The coffee shop setting lends itself to these intimate conversations between the cast, exploring key themes from the episode while also paying homage to a type of space where creatives work and thrive.

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S4 Ep 1: Lowkey Feelin' Myself

Creator and star Issa Rae and showrunner Prentice Penny break down the first episode and how they’re setting the tone for the rest of the season.

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S4 Ep 2: Lowkey Distant

Issa Rae and Prentice Penny sit down with Yvonne Orji to unpack Molly’s relationship with Andrew and Issa’s friendship with Condola.

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S4 Ep 3: Lowkey Thankful

Issa Rae and Prentice Penny are joined by Christina Elmore to discuss Condola and Lawrence’s interesting first Thanksgiving together and debate whether or not it’s possible to be friends with an ex.

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S4 Ep 4: Lowkey Losin' It

Issa Rae and Prentice Penny sit with Natasha Rothwell to discuss the shifting dynamics within the friend group.

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S4 Ep 5: Lowkey Movin' On

Issa Rae, Prentice Penny and Jean Elie discuss Issa and Molly’s blowout fight as well as the dynamic between Ahmal and Kelli.

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S4 Ep 6: Lowkey Done

Issa Rae and Prentice Penny unpack Issa’s mindset after her fight with Molly at the block party.

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S4 Ep 7: Lowkey Trippin'

Issa Rae and Prentice Penny are joined by Alexander Hodge to talk about what Molly and Andrew learn about themselves and their relationship during their first vacation together.

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S4 Ep 8: Lowkey Happy

Issa Rae, Prentice Penny and Jay Ellis dive deep into the unfinished business Lawrence and Issa have with each other.

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S4 Ep 9: Lowkey Trying

Issa Rae and Prentice Penny are joined by Kendrick Sampson to discuss Nathan’s lingering feelings for Issa and destigmatizing mental illness.

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S4 Ep 10: Lowkey Lost

Issa Rae and Prentice Penny sit down with Amanda Seales to unpack the finale.