"When I Look Upon the Stars" started with Aeroplane Kei (Leo KU, the character Kei means a kind of chess) visited his girlfriend June (Anita CHAN) in Japan for his leave from Shenzen to give her a surprise. However, June's heart has been away from Kei while started the relationship with Kei's best friend Sam (Sam LEE). Sam came to Japan for being a comic artist while he took care of June while he is a guy who always sticks with local girls. Kei tried to get back the relationship but he failed while June sticked to Sam. Kei get lost for his hearts and he accidentally met Kiki (HSU Chi) who worked as a model and waitress. Kiki tried to comfort Kei but subsequently she lost her boy. Two broken hearts resulted that Kiki asked Kei to be his boy for 24 hours while Kei accepts.