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.

• Nick Hornby
• Veronica West
• Sarah Kucserka

• Nadine Malouf
• Rainbow Sun Francks
• Debbie Harry