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.

Trying to understand why her relationships fail, Rob decides to track down her top five heartbreaks.

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.