A system and method of advertising based on the automatic determination of an advertising recipient's location and inferences of preferences derived from usage behaviors is disclosed. The advertising recipient's location that is considered in delivering a specific advertisement may be the current location or one or more historical locations. Proximity considerations with regard to other people, locations, or physical objects may influence the advertisement that is to be delivered. The advertisement may be delivered to a mobile device that has location-aware capabilities such as a Global Positioning System-based system.