In some examples, at least one processor executes instructions to, during a chat session, obtain, from a computing device of a first user, session data associated with the chat session and a first user, obtain a first set of data identifying a set of price drop items associated with the chat session, and obtain a second set of data identifying a set of attribute values associated with one or more attribute features of each item type. Based on the first set of data and the second set of data, a third set of data including affinity value data for each price drop item is generated. A fourth set of data identifying a set of items each with a score is obtained. A fifth set of data is then generated based on the third set of data and the fourth set of data.