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.

In hopes of understanding why her relationships continue to fail, Rob decides to track down her Top 5 Heartbreaks. What starts out as a satisfying romp down memory lane, ultimately leads her to the one conversation she’s been avoiding. Meanwhile, Cherise starts to put her musical talents out there.