Techniques are described for providing automated functionality to assist a user in purchasing an item for a recipient. An automated system may track various information about a series of item purchases from one or more services through which items can be purchased, and use information about past item purchases to provide various automated functionality for users that want to purchase items for various recipients. Types of functionality provided by the system include assisting in preventing recipients from receiving inappropriate items by monitoring item gift purchases and item self-purchases and responding to user requests to determine whether a specified gift would be appropriate for a recipient. In addition to information about past item purchases (e.g., whether a recipient has already received a copy of an item), the system can also use other information when determining whether a purchase of an item for the recipient is appropriate.