Tokimeki Memorial Pocket is a Simulation game, developed by KCEK and published by Konami, which was released in Japan in 1999. Because of the Gameboy's cartridge limitations, the number of girls had to be split off across two cartridges. Despite this, both games manage to hold a handful of voice samples for each girl. Additionally, three new girls were added to the Pocket editions, being Naomi Munakata, Kyoko Izumi, and Patricia McGrath.

The date is April 1997. You begin attending Kirameki High School when you learn your neighbor and friend from childhood, Shiori Fujisaki (long redheaded girl), is one of your classmates. You make it your goal to make her fall in love with you within three years and on graduation day, have her confess her love to you. Of course, there are other girls in your school as well. What will your future hold with them? Only time can tell...

This is the basic story line of Tokimeki Memorial. Impress other girls through academic and athletic skills, and take them out on dates. Sound too easy? Not so, because in between all of this high school romance, you must juggle exams, sports competitions, fashion trends, and much more all while maintaining a good relationship with the ladies. And you don't bring only one of the girls out on dates: you have to plan dates with all of them! Patricia (short blonde girl), for example, will not be happy with you if you don't maintain good status with her friends. Also, if you spend time studying, for example, your athletic abilities will decrease, as well as increase you stress level, and decrease your stamina and amusement! You need to balance these all out in order to excel. Now does it sound as easy?

This game is also available in two versions: sports and culture. In the sports version, you have a yearly competition with sports clubs from other schools, whereas the culture version, you create an exhibit on culture.