A system and method are disclosed that enable an online real-time ad viewer to interact with an ad assistant for information about the advertised product or service. When the ad viewer opens an ad, the system analyzes and matches a human ad assistant who may be capable of describing the product/service to the user. The system may match ad viewers to ad assistants based on viewer-selected preferences (e.g. talkativeness, personality type, language, cognitive abilities). The online ad viewer could then interact with the ad assistant through a webcam in real-time. The system tailors an online ad experience with a human touch which may lead to more confident purchases by the customer end and makes advertisements more efficient. The system may a...