After a first date with nice guy Clyde goes wrong, 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; Cherise and Simon take Rob to a concert, where she meets 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 finds sympathy in an unexpected place, Liam; when her night with Liam ends with a thud, Rob realizes she may be stuck in a pattern only she can break.

In hopes of understanding why her relationships continue to fail, Rob decides to track down her top five heartbreaks; what starts out as a satisfying romp down memory lane ultimately leads her to the one conversation she has been avoiding.

Rob gets a call about a rare record collection and calls up her friend, Clyde, to join her on an adventure uptown -- but friendship may not be what either really wants.

On a busy Saturday at Championship Vinyl, Rob and Cherise run after two teens who steal records; when Liam returns from tour, Rob is caught between the fantasy of a night spent backstage as a rock star's date and the reality of what Clyde offers.