A weight management system can be implemented which assists a user in losing a target amount of weight before the conclusion of a weight loss program. Such a system can assign the user to a behavioral segment, and may further assign the user to an attitudinal segment as well. The weight management system can provide recommendations for the user's diet and exercise based on health information provided by the user and the segment or segments to which the user is assigned. These recommendations can be updated during the course of the weight loss program based on the user's continued progress or lack of the same.