After a first date gone wrong with Clyde, a "nice guy," record store owner Rob Brooks recounts her Top Five Heartbreaks and a recent emotional run in with her past.

Rob stews over her recent encounter with Mac and builds a secret playlist. Simon and Cherise take Rob to a concert, where she meets the lead singer, Liam - who might just be the distraction she needs.

Rob obsesses over the identity of Mac's new girlfriend, falling deeper into the rabbit hole – and finally finding sympathy for her predicament in an unexpected place: Liam. But when her night with Liam ends with a thud, Rob realizes she may be stuck in a pattern that only she can break.

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.

Rob receives a call about a rare record collection and calls up her friend Clyde to join her on an adventure up town. But is friendship really what either of them wants?