Rob Brooks, a female record store owner in the rapidly gentrified neighborhood of Crown Heights, Brooklyn revisit past relationships through music and pop culture, while trying to get over her one true love.

Zoë Kravitz
Robyn "Rob" Brooks

David H. Holmes
Simon

Da'Vine Joy Randolph
Cherise

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In hopes of understanding why her relationships continue to fail, Rob decides to track down her Top 5 Heartbreaks. What starts out as a satisfying romp down memory lane, ultimately leads her to the one conversation she’s been avoiding. Meanwhile, Cherise starts to put her musical talents out there.
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