System and method of generating digital item recommendations

A server for generating digital item recommendations for a given user of an online recommendation platform hosted by the server, the online recommendation platform hosting a plurality of digital items, the server comprising a processor and a non-transitory computer-readable memory storing instructions, and the processor, upon executing the instructions, being configured to:

• generate a set of digital items to be recommended to the given user, the generating being based on past user interactions with the online recommendation platform,
• the set of digital items including:
• a sub-set of core digital items selected for the user based on the past user interactions, for a given core digital item of the sub-set of core digital items, the set of digital items further including:
• at least one auxiliary digital item to be provided to the given user in response to a respective user interaction of the given user with the given core digital item during appreciation thereof,
• the at least one auxiliary digital item having been determined based on (i) past user interactions of the given user with the plurality of digital items and (ii) an assumption that the given user has executed the respective user interaction with the given core digital item;
• and
• transmit the set of digital items to an electronic device associated with the given user.