After a first date gone wrong with 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 Cameron's big news about Mac, falling deeper into the rabbit hole when Cameron lets slip another detail that makes things worse for Rob. She finally finds sympathy for her predicament in an unexpected place.
In hopes of understanding why her relationships continue to fail, Rob decides to track down her All-Time Top Five Most Memorable Heartbreaks, finally confronting Mac about their unfinished business.
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.
Rob reconnects with Liam when he returns from tour. His band has blown up and Rob is caught in the fantasy of dating a musician. But the reality of what Clyde is offering acts as a counterweight.
Rob has a run in with Mac and his fiancée, Lily at Cameron's "Last Hurrah" party. She calls Clyde for back up, but things get complicated when true feelings rise to the surface.
It's Simon's turn to recount his Top 5 Most Memorable Heartbreaks. This might explain why he's been so nervous around his Barista crush and his jaded outlook on love.
Rob reflects on the night of her birthday, where we learn she finally got clarity on her feelings about Mac. Cam and Nikki's baby finally arrives, prompting Rob to finally take a chance and go after what she really wants.
