Single and in his mid-thirties, Derek re-enters the dating world after back-to-back, long-term relationships. Follow his messy journey as he shares his desperate dating adventures with his best friend, Jalen, and their favorite bartender, Lia.
Latest episodes
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19 min
Episode 10 - Nice To Meet You, Derek
After getting overwhelmed and running from life, Derek returns with a new-ish outlook on life.
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15 min
Episode 9 - Order in the Bar
Derek and Lia finally go on their "date" and Jalen becomes the voice of reason.
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19 min
Episode 8 - Turning the Paige
Paige's resurfacing and Jalen's surgery finally push Derek into therapy. See how it all plays out.
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20 min
Episode 7 - Ballsy Move
Jalen talks to his therapist as his surgery date gets closer and Derek doesn't know what he wants.
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21 min
Episode 6 - RIP Malik
Derek goes on a date with Lia’s friend, Whit. See how he ends up crying in a cemetery for the first date.
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21 min
Episode 5 - Drunk In Love
Jalen, Malcolm, and a reluctant Derek head out for a night on the town, joined by Lia and her friend Whit. Drinks are poured, feelings are shared, and secrets are spilled.
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20 min
Episode 4 - Mothaf**ka
Jalen tries to hook Derek up with a woman 16 years older. Does Derek hit it off with the cougar or is he too wet behind the ears for her?
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21 min
Episode 3 - Finessed
Derek explains to Jalen and Lia how his last date left him with a black eye and stolen wallet.
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19 min
Episode 2- Black Enough
Derek deals with his interracial dating insecurities by lying to his date about his dating history.
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18 min
Episode 1 - Bull, SH*T
Derek, desperate to regain his confidence, inexplicably arranges a date with a married woman seeking a 'special experience'. Follow him as he recounts his journey to find love to h…