As record store owner Rob Brooks tries to get back on the dating scene, her first date with a nice guy ends badly. She starts counting down her top five breakups, while she meets a face from her past.
After her recent meeting with Mac makes her agitated, Rob decides to make a secret playlist. Rob meets the musician Liam after she goes to a concert with Simon and Cherise.
After Rob's brother, Cameron, tells her about Mac's big news, Rob finds herself falling into a state of depression, as she becomes obsessed with knowing all the details. Rob finds solace in the most surprising place.
As she attempts to figure out why her love life is a complete disaster, Rob sets out to find her Top Five Heartbreaks. As she starts with Mac, her latest ex-boyfriend, she tries to get closure to their failed relationship.
As Rob asks her friend Clyde to accompany her on a trip uptown after she gets a call regarding a collection of vintage records, she wonders if she might have feelings for Clyde.
As Rob runs into Liam again, she becomes fascinated with the idea of dating a musician. But she starts to reconsider her feelings as Clyde comes into the picture.
Rob runs into an awkward situation when she meets Mac and his fiancée Lily at a party. As she turns to Clyde for emotional support, things get complicated between them.
As Rob's friend, Simon, looks back at his failed relationships as well, new discoveries about his Barista crush comes to the surface, which also sheds light on why his view on love isn't very promising.
As Rob's birthday approaches, she finds herself coming to terms with her failed relationship with Mac. She begins to face her past choices.
As Rob finally becomes ready to put her past relationship with Mac behind her, she starts to look forward to the future. When Cam and Nikki have a new baby, it encourages Rob to begin a new chapter in her life and follow her heart.