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.
Rob has a run-in with Mac and his fiancee, Lily, at Cameron's Last Hurrah party; she calls Clyde for backup, but things become complicated when true feelings rise to the surface.
It is Simon's turn to recount his top five most memorable heartbreaks, which might explain his jaded outlook on love and why he has been so nervous around his barista crush.
A milestone birthday forces Rob to confront her past and the end of her relationship with Mac.
The sudden closing of their beloved venue, DeSalle's, sends Rob on a quest to recapture the past -- if only for a night; Simon and Cherise take bold steps in their personal lives, and it may be time for Rob to do the same.