After a failed first date with a nice guy, record store owner Rob Brooks recounts her top five heartbreaks.

Rob stews over her recent encounter with Mac; 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 realises 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.