After a first date and hookup gone wrong with nice guy, Clyde, record store owner, Rob Brooks, goes into an emotional tailspin in which she recounts the ups and downs of her All-Time Top Five Most Memorable Heartbreaks: childhood sweetheart Kevin Bannister, cool girl Kat Monroe, guy who gets her Simon Miller, off-limits Justin Kit, and perfect match Russell „Mac” McCormack. Rob also reveals the impact of an unexpected encounter.