Hyperlinked icons, images, and emoji may be shared by users in a real-time messaging environment, such as text messaging. A user may send a message including a clickable emoji to a receiving user, where the received clickable emoji is displayed in the message. If the received clickable emoji is selected by the receiving user, web content linked to the emoji is retrieved and displayed. Messaging server(s) monitor messages, events, and social trends collecting contextual data. Content providers use collected contextual data to efficiently deliver targeted content.